WorldWideScience
 
 
1

Palladium-catalyzed carbon-monoxide-free aminocarbonylation of aryl halides using N-substituted formamides as an amide source.  

Science.gov (United States)

A carbon-monoxide-free aminocarbonylation of various N-substituted formamides with aryl iodides and aryl bromides using palladium acetate and Xantphos is described. The developed methodology is applicable for a wide range of formamides and aryl halides containing different functional groups furnishing good to excellent yield of the corresponding products. N-substituted formamides are used as an amide source wherein a Vilsmeier-type intermediate plays a major role, thus eliminating the need of toxic carbon monoxide gas. PMID:21618964

Sawant, Dinesh N; Wagh, Yogesh S; Bhatte, Kushal D; Bhanage, Bhalchandra M

2011-06-09

2

Palladium-catalyzed carbon-monoxide-free aminocarbonylation of aryl halides using N-substituted formamides as an amide source.  

UK PubMed Central (United Kingdom)

A carbon-monoxide-free aminocarbonylation of various N-substituted formamides with aryl iodides and aryl bromides using palladium acetate and Xantphos is described. The developed methodology is applicable for a wide range of formamides and aryl halides containing different functional groups furnishing good to excellent yield of the corresponding products. N-substituted formamides are used as an amide source wherein a Vilsmeier-type intermediate plays a major role, thus eliminating the need of toxic carbon monoxide gas.

Sawant DN; Wagh YS; Bhatte KD; Bhanage BM

2011-07-01

3

N-substituted-1-deoxynojirimycin compound and preparation thereof  

UK PubMed Central (United Kingdom)

The invention belongs to the technical field of organic chemistry and pharmaceutical chemistry, and particularly relates to an N-substitution-1-deoxynojirimycin compound and a method for preparing the same. Derivatives of 5-substitution amino ribose furanoside, under the actions of alkali triethylamine or/and a methanol solution of sodium methoxide, or/and methanol solution of potassium carbonate, or/and methanol solution of sodium hydroxide, or/and methanol solution of potassium hydroxide, are stirred at the room temperature, and the obtained product reacts with Ac2O to obtain the N-substitution-1-deoxynojirimycin compound. The compound and the method have the characteristics of easy obtaining of the reagents, low cost, simple operation and easy industrialization.

HUAWU SHAO; HAIRONG LUO

4

Alpha-amido-N-substituted amide compounds, medicament composition containing the same and use thereof  

UK PubMed Central (United Kingdom)

The invention belongs to the field of pharmaceutical chemistry, and discloses alpha-amido-N-substituted amide compounds or pharmaceutically accepted salts thereof having a structural formula as below. The invention also discloses pharmaceutical compositions containing the compounds or the pharmaceutically accepted salts thereof. The alpha-amido-N-substituted amide compounds or the pharmaceutically accepted salts thereof have anti-tumor and/or anti-cancer activities both in vitro and in vivo, can effectively resist various tumor cells and/or cancer cells, and can be used for preparing medicines for treating tumor and/or cancer.

FAJUN NAN; JIA LI; JIAN DING; GANG LIU; CHUANMING XIE; ZEHONG MIU; WANYI TAI

5

N-substituted indenoisoquinolines and syntheses thereof  

UK PubMed Central (United Kingdom)

N-Substituted indenoisoquinoline compounds, and pharmaceutical formulations of N-substituted indenoisoquinoline compounds are described. Also described are processes for preparing N-substituted indenoisoquinoline compounds. Also described are methods for treating cancer in mammals using the described N-substituted indenoisoquinoline compounds or pharmaceutical formulations thereof.

CUSHMAN MARK S; MORRELL ANDREW E; NAGARAJAN MUTHUKAMAN; POMMIER YVES G; AGAMA KELI K; ANTONY SMITHA

6

Hemoglobin adducts of N-substituted aryl compounds in exposure control and risk assessment.  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Arylamines, nitroarenes, and azo dyes yield a common type of metabolite, the nitroarene, which produces a hydrolyzable adduct with protein and is closely related to the critical, ultimate toxic and genotoxic metabolite. The target dose as measured by hemoglobin adducts in erythrocytes reflects not o...

Neumann, H G; Birner, G; Kowallik, P; Schütze, D; Zwirner-Baier, I

7

N-substituted iminodiacetic acids  

International Nuclear Information System (INIS)

[en] The chemical preparation of several new N-substituted iminodiacetic acid derivatives are described. These compounds when complexed with sup(99m)Tc provide useful radiopharmaceuticals for the external imaging of the hepatobiliary system. (U.K.)

1982-01-01

8

Evaluation of N-substitution in 6,7-benzomorphan compounds.  

UK PubMed Central (United Kingdom)

6,7-benzomorphan derivatives, exhibiting different mu, delta, and kappa receptor selectivity profiles depending on the N-substituent, represent a useful skeleton for the synthesis of new and better analgesic agents. In this work, an aromatic ring and/or alkyl residues have been used with an N-propanamide or N-acetamide spacer for the synthesis of a new series of 5,9-dimethyl-2'-hydroxy-6,7-benzomorphan derivatives (12-22). Data obtained by competition binding assays showed that the mu opioid receptor seems to prefer an interaction with the 6,7-benzomorphan ligands having an N-substituent with a propanamide spacer and less hindered amide. Highly stringent features are required for delta receptor interaction, while an N-acetamide spacer and/or bulkier amide could preferentially lead to kappa receptor selectivity. In the propanamide series, compound 12 (named LP1) displayed high mu affinity (Ki=0.83 nM), good delta affinity (Ki=29 nM) and low affinity for the kappa receptor (Ki=110 nM), with a selectivity ratio delta/mu and kappa/mu of 35.1 and 132.5, respectively. Further, in the adenylyl cyclase assay, LP1 displayed a mu/delta agonist profile, with IC50 values of 4.8 and 12 nM at the mu and delta receptors, respectively. The antinociceptive potency of LP1 in the tail-flick test after sc administration in rat was comparable with the potency of morphine (ED50=2.03 and 2.7 mg/kg, respectively), and was totally reversed by naloxone. LP1, possessing a mu/delta agonist profile, could represent a lead in further developing benzomorphan-based ligands with potent in vivo analgesic activity and a reduced tendency to induce side effects.

Pasquinucci L; Prezzavento O; Marrazzo A; Amata E; Ronsisvalle S; Georgoussi Z; Fourla DD; Scoto GM; Parenti C; Aricò G; Ronsisvalle G

2010-07-01

9

Evaluation of N-substitution in 6,7-benzomorphan compounds.  

Science.gov (United States)

6,7-benzomorphan derivatives, exhibiting different mu, delta, and kappa receptor selectivity profiles depending on the N-substituent, represent a useful skeleton for the synthesis of new and better analgesic agents. In this work, an aromatic ring and/or alkyl residues have been used with an N-propanamide or N-acetamide spacer for the synthesis of a new series of 5,9-dimethyl-2'-hydroxy-6,7-benzomorphan derivatives (12-22). Data obtained by competition binding assays showed that the mu opioid receptor seems to prefer an interaction with the 6,7-benzomorphan ligands having an N-substituent with a propanamide spacer and less hindered amide. Highly stringent features are required for delta receptor interaction, while an N-acetamide spacer and/or bulkier amide could preferentially lead to kappa receptor selectivity. In the propanamide series, compound 12 (named LP1) displayed high mu affinity (Ki=0.83 nM), good delta affinity (Ki=29 nM) and low affinity for the kappa receptor (Ki=110 nM), with a selectivity ratio delta/mu and kappa/mu of 35.1 and 132.5, respectively. Further, in the adenylyl cyclase assay, LP1 displayed a mu/delta agonist profile, with IC50 values of 4.8 and 12 nM at the mu and delta receptors, respectively. The antinociceptive potency of LP1 in the tail-flick test after sc administration in rat was comparable with the potency of morphine (ED50=2.03 and 2.7 mg/kg, respectively), and was totally reversed by naloxone. LP1, possessing a mu/delta agonist profile, could represent a lead in further developing benzomorphan-based ligands with potent in vivo analgesic activity and a reduced tendency to induce side effects. PMID:20599386

Pasquinucci, Lorella; Prezzavento, Orazio; Marrazzo, Agostino; Amata, Emanuele; Ronsisvalle, Simone; Georgoussi, Zafiroula; Fourla, Danai-Dionysia; Scoto, Giovanna M; Parenti, Carmela; Aricò, Giuseppina; Ronsisvalle, Giuseppe

2010-06-09

10

Screening candidate anticancer drugs for brain tumor chemotherapy: pharmacokinetic-driven approach for a series of (E)-N-(substituted aryl)-3-(substituted phenyl)propenamide analogues.  

UK PubMed Central (United Kingdom)

A pharmacokinetic [PK]-driven screening process was implemented to select new agents for brain tumor chemotherapy from a series of low molecular weight anticancer agents [ON27x] that consisted of 141 compounds. The screening procedures involved a combination of in silico, in vitro and in vivo mouse studies that were cast into a pipeline of tier 1 and tier 2 failures that resulted in a final investigation of 2 analogues in brain tumor-bearing mice. Tier 1 failures included agents with a molecular weight of > 450 Da, a predicted log P (log P) of either <2 or > 3.5, and a cytotoxicity IC(50) value of > 2 uM. Next, 18 compounds underwent cassette dosing studies in normal mice that identified compounds with high systemic clearance, and low blood-brain barrier [BBB] penetration. These indices along with a derived parameter, referred to as the brain exposure index, comprised tier 2 failures that led to the administration of 2 compounds [ON27570, ON27740] as single agents [discrete dosing] to mice bearing intracerebral tumors. Comparison of ON27570's resultant PK parameters to those obtained in the cassette dosing format suggested a drug-drug interaction most likely at the level of BBB transport, and prompted the use of the in vitro MDCK-MDR1 transport model to help assess the nature of the discrepancy. Overall, the approach was able to identify candidate compounds with suitable PK characteristics yet further revisions to the method, such as the use of in vitro metabolism and transport assays, may improve the PK-directed approach to identify efficacious agents for brain tumor chemotherapy.

Lv H; Wang F; Reddy MV; Zhou Q; Zhang X; Reddy EP; Gallo JM

2012-12-01

11

Photolytic inhibition and labeling of proteins with aryl diazonium compounds  

International Nuclear Information System (INIS)

In the course of preparing aryl azide derivatives for use as photoprobes, we have observed significant light sensitivity in the precursor aryl diazonium compounds. The photosensitive properties of this class of compounds are of interest since they will seek out cationic binding sites in biological targets, and can be employed to inhibit complementary targets at acid pH. The relationship between photolytic change in the structure of diazonium compounds and the corresponding change in function of a biological target are presented. Experiments are described in which the dark and light sensitive properties of a model diazonium compound, diazobenzene sulfonate (DBS), were determined. The ultraviolet spectra were used to evaluate the dark stability and light sensitivity og DBS. Chymotrypsin and trypsin served as functioning targets for further evaluation of the photochemical properties. Both enzymes are stable to the probe in the dark at acid pH. A rapid loss of enzyme activity was observed following flash photolysis of DBS-enzyme solutions. Photolytic incorporation of radioactive DBS into chymotrypsin was observed. Aryl diazonium salts can be employed to probe the availability of complementary sites in biological targets at different acid pH values. (Author)

1978-01-01

12

Ortho Metalation of n-Substituted Benezene-Sulfonamides by Excess n-Butyllithium. Condensation with Carbonyl Compounds. cyclizations.  

Science.gov (United States)

It was found that N-methyl- and N-phenyl-benzenesulfonamides undergo ortho metalation, as well as N-metalation, with excess n-butyllithium to form dilithiosulfonamides, as evidenced by condensations with carbonyl compounds to give ortho derivatives. Ortho...

H. Watanabe R. L. Gay C. R. Hauser

1968-01-01

13

ANTI-PROLIFERATIVE COMPOUNDS FROM A 3-ARYL-COUMARINE OR 3-ARYL-QUINOLIN-2-ONE AND USES THEREOF  

UK PubMed Central (United Kingdom)

The present invention is directed to molecules deriving from a 3-aryl-coumarine or 3-aryl-quinolin-2-one and having potent anti-proliferative and/or cytotoxic activity, especially against tumoral cells. The present invention also concerns the uses of these molecules in therapeutic application, for the treatment of different cancers. The invention also discloses the use of said compound for the manufacture of a medicament for treating cancer. The invention also concerns a process for inhibiting cell proliferation comprising contacting said cells with a compound of the invention.

SCHAPIRA MATTHIEU; LAMIGEON CYRILLE; GUTMANN MATHIEU; BARTHELAIX AUDREY; HUGO NICOLAS; COLAS PIERRE

14

Synthesis of C-2 Arylated Tryptophan Amino Acids and Related Compounds through Palladium-Catalyzed C-H Activation.  

UK PubMed Central (United Kingdom)

Tryptophan (Trp) and tryptophan derivatives are C2-arylated. A C-H activation process allows the preparation of both protected and unprotected arylated-Trp amino acids, directly from the amino acid precursor and aryl iodides. The obtained compounds are suitable for standard solid-phase peptide synthesis.

Preciado S; Mendive-Tapia L; Albericio F; Lavilla R

2013-08-01

15

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds  

Digital Repository Infrastructure Vision for European Research (DRIVER)

N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple a...

Carolin Fischer; Burkhard Koenig

16

New N-substituted azinylalkyl-azincarboxamide compounds useful e.g. in plant protection, for combating animal pests, arthropods, nematodes and plant diseases, and for protecting industrial materials against attack and destruction by insect  

UK PubMed Central (United Kingdom)

N-Substituted azinylalkyl-azincarboxamide compounds (I), and their analogs, salts and N-oxides are new. N-Substituted azinylalkyl-azincarboxamide compounds of formula (I), and their analogs, salts and N-oxides are new. X : O or S A 1>-A 4>N or C-Y 1>, provided that more than two N atoms are not in adjacent position A 5>CH or N either Y 1>1-8C alkyl, 1-8C haloalkyl, 1-8C alkoxy, 1-8C alkylthio, 1-8C alkylsulfinyl, 1-8C alkylsulfonyl, 1-8C alkylamino, di(1-8C)-alkylamino, (hetero)aryl or heterocyclyl (all optionally substituted), H, nitro, amino, CN or halo or two adjacent Y 1>5- to 6-membered ring system R 2>H or 1-8C alkyl, 1-8C alkyl 3-7C cycloalkyl, 4-9C spirocycloalkyl or 1-8C alkoxycarbonyl (all optionally substituted) and R 1>1-8C alkyl, 3-7C cycloalkyl, 1-8C alkyl(3-7C)-cycloalkyl, 3-10C alkylalkenyl, 2-9C alkenyl, 2-9C alkylcarbonyl, 4-8C cycloalkylcarbonyl, arylcarbonyl, 1-8C alkoxycarbonyl, 1-8C alkylsulfonyl, arylsulfonyl, 1-6C-alkoxy-carbonylcarbonyl, aryloxycarbonyl-carbonyl, 1-8C alkylamino-thiocarbonyl, 3-7C cycloalkylaminothiocarbonyl, -C(=O)-cyclobutane, -C(=O)-(CH 2) 2-CH 3, -C(=O)-CH(CH 3) 2, -C(=O)-(CH 2) 4-CH 3, -C(=O)-(CH 2) 5-CH 3, -C(=O)- cyclohexane, -C(=O)-CH 2-CH 3, -C(=O)-cyclopentane, -C(=O)-(CH 2) 3-CH 3, chloro-phenyl groups of formula (Q-10) or (Q-11), -C(=O)-O-CH 2-CH(CH 3) 2, -C(=O)-O-CH 2-CH 3, -C(=O)-O-(CH 2) 2-O-CH 3, -C(=O)-CH 2-CH(CH 3) 2, -C(=O)-O-CH 2-C?=CH, -C(=CH-CH(CH 3) 2)(O-C(=O)-CH 2-CH(CH 3) 2), -C(=O)-cyclopropane, -C(=O)-O-CH 2-phenyl, -C(=O)-O-(CH 2) 2-CH 3, -C(=O)-O-CH 2-C?=C-CH 3, phenyl group of formula (Q-22), -C(=O)-O-CH 2-CH(Cl) 3, cyclopropane group of formula (Q-24), -C(=O)-O-CH(CH 3) 2, -C(=S)-O-phenyl, -C(=O)-C(CH 3) 3, -C(=O)-O-CH 3, adamantane group of formula (Q-29), dimethyl-cyclopropane group of formula (Q-30), 2,4-dichlorobenzene group of formula (Q-31), trifluoromethyl-benzene group of formula (Q-32), methyl-benzene group of formula (Q-33), methoxy-benzene group of formula (Q-34), 3,4-dichlorobenzene group of formula (Q-35), fluorobenzene group of formula (Q-36), biphenyl group of formula (Q-37), cyclopropane groups of formula (Q-38)-(Q-44), -C(=O)-CH 3, -CH 2-CH=CH 2, -(CH 2) 2-CH 3, -CH 2-CH 3, cyclopropane group of formula (Q-49), phenyl groups of formula (Q-50) or (Q-51), cyclopropane groups of formula (Q-52)-(Q-55), -(CH 2) 5-CH 3, phenyl groups of formula (Q-57) or (Q-58), -S(=O) 2-CH 3, phenyl groups of formula (Q-60)-(Q-66), -C(=O)-C(=O)-O-CH 2-CH 3, -(CH 2) 3-CH 3, -(C=O)-O-(CH 2) 2-CH(CH 3) 2, -C(=O)-O-CH 2-C(=CH 2)-CH 3, -C(=O)-O-CH 2-CH=CH 2, phenyl groups of formula (Q-72)-(Q-74), -C(=O)-O-C(CH 3) 3, phenyl groups of formula (Q-76)-(Q-80), -C(=S)-NH-cyclopropane, -C(=S)-NH-CH 2-cyclopropane, -C(=S)-NH-CH 2-CH 3, -CH 2-CH(CH 3) 2, -CH 2-cyclopropane, -(CH 2) 2-CH=CH 2, CH 3 or phenyl group of formula (Q-84). [Image] [Image] [Image] [Image] [Image] [Image] [Image] [Image] [Image] [Image] - ACTIVITY : Plant Protectant Arthropodicide Nematocide Insecticide Antifouling Arachnicide Acaricide Antiparasitic Antihelmintic Protozoacide. - MECHANISM OF ACTION : None given.

FRACKENPOHL JENS; HENSE ACHIM; ARNOLD CHRISTIAN; FRANKEN EVA-MARIA; MALSAM OLGA; SANWALD ERICH; GOERGENS ULRICH

17

N-(substituted arylmethyl)-4-(disubstituted methyl)piperidines and piperazines  

UK PubMed Central (United Kingdom)

It has now been found that certain novel N-(substituted aryl)-4-(disubstituted methyl)piperidine and pyridine derivatives have provided unexpected insecticidal activity. These compounds are represented by formula (I): wherein m, n, q, r, and s are independently selected from 0 or 1; and p is 0, 1, 2, or 3; A is CH or N; and B, D, E, R, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7 >and R<8 >are fully described herein. In addition, compositions comprising an insecticidally effective amount of at least one compound of formula I, and optionally, an effective amount of at least one of a second compound, with at least one insecticidally compatible carrier are also disclosed; along with methods of controlling insects comprising applying said compositions to a locus where insects are present or are expected to be present.

DING PING; HENRIE ROBERT N.II; LYGA DANIEL H; LYGA JOHN W; ROSEN DAVID S; ZHANG QUN; YEAGER WALTER H; DONOVAN STEPHEN F; ZHANG STEVEN S; SHULMAN INNA; WANG GUOZHI; ZHANG Y L; GOPALSAMY ARIAMALA; WARKENTIN DENNIS L; RENSNER PAUL E; SILVERMAN IAN R; CULLEN THOMAS G; HENRIE II ROBERT N; COHEN DANIEL H; THEODORIDIS GEORGE; ZHANG STEVEN SHUNXIANG; YU SEONG JAE; ZHANG Y. LARRY

18

Arylgold(I) and aryl(triphenylphosphine)gold(I)compounds  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Novel monomeric benzyl- and aryl-gold(I) triphenylphosphine complexes have been prepared. Pure, uncomplexed 2-[(dimethylamino)methyl]-phenylgold(I) has been isolated from the reaction of tetranuclear bis {2-[(dimethylamino)methyl]phenyl}goldlithium (R4 Au2 Li2) with trimethyltin bromide.

Koten, G. van; Noltes, J.G.

19

Arylgold(I) and aryl(triphenylphosphine)gold(I) compounds  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Novel monomeric benzyl- and aryl-gold(I) triphenylphosphine complexes have been prepared. Pure, uncomplexed 2-[(dimethylamino)methyl]-phenylgold(I) has been isolated from the reaction of tetranuclear bis {2-[(dimethylamino)methyl]phenyl}goldlithium (R{4} Au{2} Li{2}) with trimethyltin bromide.

Koten, G. van; Noltes, J.G.

20

SUBSTITUTED 1-(AZOLIN-2-YL)-AMINO-2-ARYL-1-HETARYL-ETHANE COMPOUNDS  

UK PubMed Central (United Kingdom)

The present invention relates to 1-(azolin-2-yl)-amino-2-aryl-1-hetaryl-ethane compounds (I) and 1-(aminothiocarbonylamino)-2-aryl-1-hetaryl-ethane compounds (II) and their salts which are useful for combating animal pest, in particular insects, arachnids and nematodes. Furthermore, the present invention relates to a method for combating animal pests selected from insects, arachnids and nematodes, and to agricultural compositions for combating animal pests. Furthermore, the present invention relates to veterinary compositions for combating animal pests.

KORDES MARKUS; BREUNINGER DELPHINE; LE VEZOUET RONAN; KORADIN CHRISTOPHER; TEDESCHI LIVIO; PUHL MICHAEL; CULBERTSON DEBORAH L

 
 
 
 
21

Substituted 1-(azolin-2-yl)-amino-2-aryl-1-hetaryl-ethane Compounds  

UK PubMed Central (United Kingdom)

The present invention relates to 1-(azolin-2-yl)-amino-2-aryl-1-hetaryl-ethane compounds (I) and 1-(aminothiocarbonylamino)-2-aryl-1-hetaryl-ethane compounds (II) and their salts which are useful for combating animal pest, in particular insects, arachnids and nematodes. Furthermore, the present invention relates to a method for combating animal pests selected from insects, arachnids and nematodes, and to agricultural compositions for combating animal pests. Furthermore, the present invention relates to veterinary compositions for combating animal pests.

KORDES MARKUS; BREUNINGER DELPHINE; VEZOUET RONAN LE; KORADIN CHRISTOPHER; TEDESCHI LIVIO; PUHL MICHAEL; CULBERTSON DEBORAH L

22

SUBSTITUTED 1-(AZOLIN-2-YL)-AMINO-2-ARYL-1-HETARYL-ETHANE COMPOUNDS.  

UK PubMed Central (United Kingdom)

The present invention relates to 1-(azolin-2-yl)-amino-2-aryl-1-hetaryl-ethane compounds (I) and 1-(aminothiocarbonylamino)-2-aryl-1-hetaryl-ethane compounds (II) and their salts which are useful for combating animal pest, in particular insects, arachnids and nematodes. Furthermore, the present invention relates to a method for combating animal pests selected from insects, arachnids and nematodes, and to agricultural compositions for combating animal pests. Furthermore, the present invention relates to veterinary compositions for combating animal pests.

PUHL MICHAEL; KORDES MARKUS; CULBERTSON DEBORAH L; TEDESCHI LIVIO; KORADIN CHRISTOPHER; BREUNINGER DELPHINE; VEZOUET RONAN LE

23

ARYL HYDRAZIDE COMPOUNDS AND USAGE IN PREPARATION OF IMMUNOSUPPRESSIVE AGENT THEIROF  

UK PubMed Central (United Kingdom)

This invention relates to aryl hydrazide compounds of formula I, their geometricisomers, medical salts or hydrates, their preparation process and medical compositionscontaining the compounds. The invention also relates to usage of the said compoundsin preparation of drugs for rejection of foreign organ transplants and prophylaxisand/or treatment of certain auto-immune diseases such as rheumatoid, psoriasis,multiple sclerosis and systemic erythema lupus: Formula (I).

LI Song; HE Xinhua; ZHENG Zhibing; LI Yan; SHEN Beifen

24

Anti-proliferative compounds deriving from a 3-aryl-coumarine or 3-aryl-quinolin-2-one and uses thereof  

UK PubMed Central (United Kingdom)

The present invention is directed to molecules deriving from a 3-aryl-coumarine or 3-aryl-quinolin- 2-one and having potent anti-proliferative and/ or cytotoxic activity, especially against tumoral cells. The present invention also concerns the uses of these molecules in therapeutic application, for the treatment of different cancers. The invention also discloses the use of said compound for the manufacture of a medicament for treating cancer. The invention also concerns a process for inhibiting cell proliferation comprising contacting said cells with a compound of the invention.

MATTHIEU SCHAPIRA; CYRILLE LAMIGEON; MATHIEU GUTMANN; AUDREY BARTHELAIX; NICOLAS HUGO; PIERRE COLAS

25

ETHER BENZYLIDENE PIPERIDINE ARYL CARBOXAMIDE COMPOUNDS USEFUL AS FAAH INHIBITORS  

UK PubMed Central (United Kingdom)

The present invention relates to compounds of Formula (I) wherein Ar is optionally substituted phenyl or 6-membered heteroaryl moiety, or a benzisoxazole, pyrrolopyridine, or benzotriazole group; or a pharmaceutically acceptable salt thereof; processes for the preparation of the compounds; intermediates used in the preparation of the compounds; compositions containing the compounds; and uses of the compounds in treating diseases or conditions associated with fatty acid amide hydrolase (FAAH) activity, including pain, urinary incontinence, overactive bladder, emesis, cognitive disorders, anxiety, depression, sleeping disorders, eating disorders, movement disorders, glaucoma, psoriasis, multiple sclerosis, cerebrovascular disorders, brain injury, gastrointestinal disorders, hypertension, or cardiovascular disease.

FAY LORRAINE KATHLEEN; JOHNSON DOUGLAS SCOTT; MEYERS MARVIN JAY; THORARENSEN ATLI; WANG LIJUAN JANE

26

ETHER BENZYLIDENE PIPERIDINE ARYL CARBOXAMIDE COMPOUNDS USEFUL AS FAAH INHIBITORS  

UK PubMed Central (United Kingdom)

The present invention relates to compounds of Formula (I) wherein Ar is optionally substituted phenyl or 6-membered heteroaryl moiety, or a benzisoxazole, pyrrolopyridine, or benzotriazole group or a pharmaceutically acceptable salt thereof processes for the preparation of the compounds intermediates used in the preparation of the compounds compositions containing the compounds and uses of the compounds in treating diseases or conditions associated with fatty acid amide hydrolase (FAAH) activity, including pain, urinary incontinence, overactive bladder, emesis, cognitive disorders, anxiety, depression, sleeping disorders, eating disorders, movement disorders, glaucoma, psoriasis, multiple sclerosis, cerebrovascular disorders, brain injury, gastrointestinal disorders, hypertension, or cardiovascular disease.

FAY LORRAINE KATHLEEN; JOHNSON DOUGLAS SCOTT; MEYERS MARVIN JAY; THORARENSEN ATLI; WANG LIJUAN JANE

27

PHOTOTHERAPY METHODS AND DEVICES COMPRISING EMISSIVE ARYL-HETEROARYL COMPOUNDS  

UK PubMed Central (United Kingdom)

Disclosed herein are compounds represented by a formula: R1-Ar1-X-Ar2-Ar3-Het, wherein R1, Ar1, X, Ar2, Ar3, and Het are described herein. Compositions and light-emitting devices related thereto are also disclosed.

MOCHIZUKI AMANE; KHAN SAZZADUR RAHMAN; LI SHENG; ZHENG SHIJUN; CAYAS JENSEN; OKADA KEISAKU; HARDING BRETT T

28

Complex aryl copolymer compounds and polymer light emitting devices made by using the same  

UK PubMed Central (United Kingdom)

The present invention provides a compound which is (a) represented by the below formula (16-1) or (16-2) in the formula, Ar 1 and Ar 2 each independently represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group X 1 and X 2 each independently represent O, S, C(=O), S(=O), SO 2 , C(R 1 )(R 2 ), Si(R 3 )(R 4 ), N(R 5 ), B(R 6 ), P(R 7 ) or P(=O)(R 8 ) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, monovalent heterocyclic group, arylalkenyl group, aryl ethynyl group, carboxyl group, or cyano group R 1 and R 2 , or R 3 and R 4 may be connected mutually to form a ring X 1 and X 2 are not the same X 1 and Ar 2 bond to adjacent carbons in the aromatic ring of Ar 1 and X 2 and Ar 1 bond to adjacent carbons in the aromatic ring of Ar 2 Y 1 and Y 2 each independently represent a halogen atom, alkylsulfonate group, arylsulfonate group, arylalkylsulfonate group, boric ester group, sulfonium methyl group, phosphonium methyl group, phosphonate methyl group, monohalogenated methyl group, boric acid group, formyl group, or vinyl group Z 1 represents a hydrogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, aryl alkylthio group, substituted amino group, substituted silyl group, monovalent heterocyclic group, arylalkenyl group, or aryl ethynyl group or (b) represented by the below formula (19): wherein R 44 represents a hydrogen atom, alkyl group, aryl group, arylalkyl group, or a monovalent heterocyclic group.

DOI SHUJI; KOBAYASHI SATOSHI; NOGUCHI TAKANOBU

29

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds.  

UK PubMed Central (United Kingdom)

N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple aromatic halides by simple amines works with many of the described methods in high yield, the reactions may require detailed optimization if applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three main N-arylation methods in their application to the synthesis of biologically active compounds: Palladium-catalysed Buchwald-Hartwig-type reactions, copper-mediated Ullmann-type and Chan-Lam-type N-arylation reactions. The discussed examples show that palladium-catalysed reactions are favoured for large-scale applications and tolerate sterically demanding substituents on the coupling partners better than Chan-Lam reactions. Chan-Lam N-arylations are particularly mild and do not require additional ligands, which facilitates the work-up. However, reaction times can be very long. Ullmann- and Buchwald-Hartwig-type methods have been used in intramolecular reactions, giving access to complex ring structures. All three N-arylation methods have specific advantages and disadvantages that should be considered when selecting the reaction conditions for a desired C-N bond formation in the course of a total synthesis or drug synthesis.

Fischer C; Koenig B

2011-01-01

30

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds.  

Science.gov (United States)

N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple aromatic halides by simple amines works with many of the described methods in high yield, the reactions may require detailed optimization if applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three main N-arylation methods in their application to the synthesis of biologically active compounds: Palladium-catalysed Buchwald-Hartwig-type reactions, copper-mediated Ullmann-type and Chan-Lam-type N-arylation reactions. The discussed examples show that palladium-catalysed reactions are favoured for large-scale applications and tolerate sterically demanding substituents on the coupling partners better than Chan-Lam reactions. Chan-Lam N-arylations are particularly mild and do not require additional ligands, which facilitates the work-up. However, reaction times can be very long. Ullmann- and Buchwald-Hartwig-type methods have been used in intramolecular reactions, giving access to complex ring structures. All three N-arylation methods have specific advantages and disadvantages that should be considered when selecting the reaction conditions for a desired C-N bond formation in the course of a total synthesis or drug synthesis. PMID:21286396

Fischer, Carolin; Koenig, Burkhard

2011-01-14

31

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds  

Directory of Open Access Journals (Sweden)

Full Text Available N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple aromatic halides by simple amines works with many of the described methods in high yield, the reactions may require detailed optimization if applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three main N-arylation methods in their application to the synthesis of biologically active compounds: Palladium-catalysed Buchwald–Hartwig-type reactions, copper-mediated Ullmann-type and Chan–Lam-type N-arylation reactions. The discussed examples show that palladium-catalysed reactions are favoured for large-scale applications and tolerate sterically demanding substituents on the coupling partners better than Chan–Lam reactions. Chan–Lam N-arylations are particularly mild and do not require additional ligands, which facilitates the work-up. However, reaction times can be very long. Ullmann- and Buchwald–Hartwig-type methods have been used in intramolecular reactions, giving access to complex ring structures. All three N-arylation methods have specific advantages and disadvantages that should be considered when selecting the reaction conditions for a desired C–N bond formation in the course of a total synthesis or drug synthesis.

Carolin Fischer; Burkhard Koenig

2011-01-01

32

Aqueous high-temperature chemistry of carbo- and heterocycles. 29. Reactions of aryl hydrocarbons, aryl N-oxides and aryl carbonyl compounds in supercritical water at 460{degree}C  

Energy Technology Data Exchange (ETDEWEB)

A series of aryl hydrocarbons, aryl N-oxides, and aryl carbonyl compounds were subjected to thermolysis at 460{degree}C in water alone, in 15% aqueous formic acid, in 15% aqueous sodium formate, and, for comparison of purely thermal reactions, in cyclohexane. The runs were carried out initially for 7 min and, in most cases, also for 1 h. The aryl carbonyl substrates underwent mainly carbonyl reduction mainly under reduction conditions, with ring opening only observed in significant amounts for 1,4-naphthoquinone and 3,4-benzocoumarin. The arenes produced mainly reduction products with only low yields of ring-opened products observed. Aryl oximes underwent significant denitrogenation and subsequent reduction with only very little cleavage to simpler aromatic systems. The N-oxides underwent deoxygenation, and in the case of isoquinoline, ring opening of the heterocyclce was prevalent. 2-Aminobiphenyl was denitrogenated and cleaved to simpler systems in cyclohexane, but in the aqueous systems it underwent mainly cyclization to yield carbazole with only low yields of denitrogenated products. 2-Phenylphenol was unreactive under aqueous conditions with only low yields of deoxygenated products observed. 11 refs., 15 figs., 1 tab.

Katritzky, A.R.; Ignatchenko, E.S.; Allin, S.M.; Barcock, R.A.; Siskin, M.; Hudson, C.W. [University of Florida, Gainesville, FL (United States). Center for Heterocyclic Compounds, Dept. of Chemistry

1997-01-01

33

Use of fused aryl compounds for coloring keratin fibers, particularly human keratin fibers such as hair  

UK PubMed Central (United Kingdom)

Use of fused aryl compounds (I) for coloring keratin fibers, particularly human keratin fibers such as hair, is claimed. Use of fused aryl compounds of formula (A-CR1=B1) (I) for coloring keratin fibers, particularly human keratin fibers such as hair, is claimed. B1 : CR2-D, CR2-A, G1a-D or CR2-G=CR3-M-A R1-R3 : H, 1-6C alkyl or 5-16 membered aryl ring D : fused or non fused 5-16 membered (hetero)aryl ring optionally substituted A : fused tricyclic groups of formula (A1)-(A6) or (A7) (when B1 is CR2-A, G-D group or -CR2=CR3-M-A group) H1 : fused or non fused 5-16 membered (hetero)aryl ring optionally substituted R4 : H, 1-6C alkyl optionally interrupted by a heteroatoms of O or S, alkyl-1-6C-hydroxyl, alkyl-1-6C-amino, 1-6C alkoxy or 1-6C alkoxyalkyl either Y1 : O, S, or amino group (NR4) Z : -C pH 2p- (optionally substituted by one or more halo, OH, alkyl, haloalkyl, alkoxy, amino, mono- or dialkylamino, or mono-or dihydroxyalkylamino) or (-C qH 2qCO-) ZNCY1 : ring q : 1-3 p : 2-4 I1, J1 : N, O, S, CR5 or NR6 R5, R6 : H, 1-6C alkyl (optionally interrupted by a heteroatom comprising O or S), alkyl-1-6C hydroxyl, alkyl 1-6C amino group, a 1-6C alkoxy, or 1-6C alkoxyalkyl I2, J2 : O, S, N, amino group (-NR7), a carbonyl group (-C=O), C=S group, or -CR8R9 either R7, R8, R9 : H, 1-6C alkyl (optionally interrupted by a heteroatom comprising O or S), alkyl-1-6C hydroxyl, alkyl-1-6C amino group, 1-6C-alkoxy or 1-6C-alkoxyalkyl or R8R9 : a 5-6 membered ring (optionally saturated and optionally comprising one or more heteroatoms) I4, J4, K4, L : N, O, S, CR10, or NR11 R10, R11 : H, 1-6C alkyl (optionally interrupted by a heteroatom comprising O or S), alkyl-1-6C hydroxyl, alkyl-1-6C amino group, 1-6C alkoxy, or 1-6C alkoxyalkyl group, provided that, in the group A4, ring comprising I4, J4, N, K4 and L is aryl I5 : O, S, N, -NR12, -C=O, C=S, or -CR13R14 J5, K5 : N, O, S, CR15 or NR16 either R12, R13, R14, R15, R16 : H, 1-6C alkyl (optionally interrupted by a heteroatom comprising O or S), alkyl-1-6C hydroxyl, alkyl-1-6C amino group, 1-6C alkoxy or 1-6C alkoxyalkyl or R13R14 : a 5-6 membered ring (optionally saturated and optionally comprising one or more heteroatoms), provided that, in groups A5, cycle comprising I5, J5, K5 and N is aryl I6, J6 : N, O, S, CR17 or -NR19 K6 : O, S, N, -NR19, a carbonyl group, C=S or -CR20R21 either R17, R18, R19, R20, R21 : H, 1-6C alkyl (optionally interrupted by a heteroatom of O or S), alkyl-1-6C hydroxyl, alkyl-1-6C amino group, 1-6C alkoxy or 1-6C alkoxyalkyl or R20R21 : a 5-6 membered ring (optionally saturated and optionally comprising one or more heteroatoms), provided that, in groups A6, ring comprising I6, J6, K6 and N is aryl X : O, S, N, -NR22, carbonyl, C=S, or -CR23R24 either R22, R23, R24 : R17 or R23R24 : a 5-6 membered ring (optionally saturated and optionally comprising one or more heteroatoms) G1a, G : groups of formula (a1)-(a5) R1a : H, halo, 1-6C alkyl, alkyl-1-6C sulfonate, alkyl-1-6C carbonylalkyl, 1-6C alkylphenyl, phenyl, diphenylamino or morpholino R2a, R3a : H, halo, 1-6C alkyl or S-phenyl and M : linear or branched 1-20-membered chain optionally interrupted by a non-aryl ring comprising a heteroatom or non heteroatom, or optionally substituted (hetero)aryl. Independent claims are included for: (1) a dye composition, for dyeing keratin fibers (preferably human keratin fibers such as hair), comprising (I) in a medium (2) process for dyeing keratin fibers comprising applying the composition on the fibers, and optionally followed by rinsing and (3) a multi-compartment device containing a first compartment containing a dye composition and a second compartment containing one or more acidifying agents, alkalizing agents, solvents and/or zinc salts. [Image] [Image

PLOS GREGORY

34

METHOD FOR PREPARING N-SUBSTITUTED ETHYL-(2-DIALKOXYPHOSPHORYL-4-CYANO)-BUTANEIMIDATES  

UK PubMed Central (United Kingdom)

FIELD: chemistry of organophosphorus compounds, chemical technology. ^ SUBSTANCE: invention relates to a novel method for preparing N-substituted phosphorylated imidates bearing cyanoethyl-group in structure. Invention describes a method for preparing N-substituted ethyl-(2-dialkoxyphosphoryl-4-cyano)butaneimidates of the formula: wherein R means (C3-C4)-alkyl or isoalkyl R' means C(O)CH3, C(O)C6H5, Si(CH3)3. Method involves interaction of N-substituted ethyl-(2-dialkoxyphosphoryl)ethaneimidates with acrylonitrile in the presence of sodium ethylate as a catalyst in dioxane medium in the mole ratio N-substituted ethyl-(2-dialkoxyphosphoryl)ethaneimidate : acrylonitrile : sodium ethylate = 1:(1.05-1.15):(0.1-0.15), respectively, at temperature 40-60oC. Invention provides preparing new chemical compounds that are perspective for preparing biologically active compounds used in medicine and agriculture. ^ EFFECT: improved preparing method. ^ 4 ex

SHISHKIN V E; MEDNIKOV E V; ANISHCHENKO O V

35

Process for preparing N-substituted amine.  

UK PubMed Central (United Kingdom)

An N-substituted amine is produced by reacting an alcohol or aldehyde with ammonia, a primary amine or a secondary amine in the presence of a catalyst comprising (1) copper, (2) a metal selected from chromium, manganese, iron, cobalt, nickel and zinc, (3) a metal of the platinum VIII group and (4) a metal selected from alkali metals and alkaline earth metals.

ABE HIROSHI; AIKAWA JUN; OKABE KAZUHIKO; SOTOYA KOHSHIRO

36

Complex aryl copolymer compounds and polymer light emitting devices made by using the same  

UK PubMed Central (United Kingdom)

The present invention provides a polymer compound comprising a repeating unit of below formula (1) or (2), and a repeating unit represented by the below formula (6), and having a polystyrene reduced number average molecular weight of 10 3 to 10 8 : wherein, Ar 1 and Ar 2 each independently represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group X 1 and X 2 each independently represent O, S, C(=O), S(=O), SO 2 , C(R 1 )(R 2 ), Si(R 3 )(R 4 ), N(R 5 ), B(R 6 ), P(R 7 ) or P(=O)(R 8 ) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, arylethynyl group, carboxyl group or cyano group R 1 and R 2 , or R 3 and R 4 may be connected mutually to form a ring X 1 and X 2 are not the same and wherein X 1 and Ar 2 bond to adjacent carbons in the aromatic ring of Ar 1 , and X 2 and Ar 1 bond to adjacent carbons in the aromatic ring of Ar 2 wherein, Ar 3 and Ar 4 each independently represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group X 3 and X 4 each independently represent N, B, P, C(R 9 ) or Si(R 10 ) R 9 and R 10 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, arylethynyl group, carboxyl group or cyano group X 3 and X 4 are not the same and wherein X 3 and Ar 4 bond to adjacent carbons in the aromatic ring of Ar 3 , and X 4 and Ar 3 bond to adjacent carbons in the aromatic ring of Ar 4 -Ar 5 -X 6 -(Ar 6 -X 7 )a-Ar 7 - (6) in the formula, Ar 5 , Ar 6 , and Ar 7 each independently represent an arylene group, divalent heterocyclic group, or divalent group having metal complex structure X 6 represents -C C-, -N(R 21 )- or -(SiR 22 R 23 )y- X 7 represents -CR 19 =CR 20 -, -C C-, -N(R 21 )- or -(SiR 22 R 23 )y- R 19 and R 20 each independently represent a hydrogen atom, alkyl group, aryl group, monovalent heterocyclic group, carboxyl group or cyano group R 21 , R 22 and R 23 each independently represent a hydrogen atom, alkyl group, aryl group, monovalent heterocyclic group or arylalkyl group a represents an integer of 0-1 and y represents an integer of 1-12.

DOI SHUJI; KOBAYASHI SATOSHI; NOGUCHI TAKANOBU

37

Synthesis and In Vitro Antigungal Properties of 4-Aryl-4-Narylamine-1-butenes and Related Compounds  

Directory of Open Access Journals (Sweden)

Full Text Available A new series of 4-aryl and 4-alkyl-4-N-arylamine-1-butenes (homoallylamines) were synthesized and some of them transformed to 4-aryl or alkylquinolines. All of them showed strong antifungal activities against human pathogenic fungi in vitro, being Epidermophyton floccosum the most susceptible species.

V. Kouznetsov; J. Urbina; A. Palma; S. López; C. Devia; R. Enriz; S. Zacchino

2000-01-01

38

Unsymmetrical alkyl aryl thiourae compounds for use as cerebral blood flow tracers. [Rats  

Energy Technology Data Exchange (ETDEWEB)

The synthesis and characterization of an homologous series of inert nonvolatile /sup 14/C-labeled unsymmetrical alkyl aryl thiourea compounds is described for their use as regional blood flow (rCBF) tracers employing autoradiographic procedures. In alert normocapnic rats the single-pass extraction values into brain for these thioureas were found ranging from 0.497 for 1-methyl-3-phenylthiourea to 0.730 for 1-butyl-3-phenylthiourea. The commonly used rCBF tracers (14C) antipyrine and (14C) iodoantipyrine had single-pass extraction values of 0.451 and 0.553, respectively. Since 1-butyl-3-phenylthiourea diffused most readily into rat brain it was chosen as a potentially valuable rCBF tracer. Employing 1-butyl-3-phenylthiourea to measure rCBF nd its empirically derived brain extraction values the following flow rates in normocapnic rats were found: 3.2 ml . g-1 . min-1 for cochlear nucleus: 3.0 for inferior colliculus; 2.5 for medical geniculate; 1.9 for pontine gray and hypothalamus; 1.7 for caudate and cerebral cortex; and 1.2 for cerebellar gray and 0.41 to 0.50 for white matter structures. It was concluded from these studies that 1-butyl-3-phenylthiourea is more advantageous than iodoantipyrine for measuring rCBF, especially in those areas that possess very rapid rates of flow.

Goldman, S.S.; Haas, W.K.; Ransohoff, J.

1980-06-01

39

Photophysical investigations on some synthesized electron donor aryl-bridged compounds  

Energy Technology Data Exchange (ETDEWEB)

The measurements of electronic absorption, steady-state fluorescence emission and time resolved transient spectra are made for two novel synthesized aryl-bridged compounds: 2,6-bis(4,5-dihydro-7,8-dimethoxy)-isoquinolino benzene(DIB) and 2,6-bis(4,5-dihydro-7,8-dimethoxy)-isoquinolino pyridine(DIP) at the ambient temperature in presence of the well-known electron acceptor 9-fluorenone (9FL). The energy positions of the absorption bands of both DIB and DIP are found to be similar to those of the corresponding bands of naphthalene and isoquinoline. Solvent effect shows that the two closely lying bands (260 and around 310 nm) of both DIB and DIP are of {pi}{pi}* type. Steady-state polarization experiments demonstrate that these two close-lying bands are responsible for two different type of transitions, 260 nm is responsible for {sup 1}L{sub a}<-{sup 1}A and 310 nm is due to {sup 1}L{sub b}<-{sup 1}A. This polarization study also shows that {sup 1}L{sub a} and {sup 1}L{sub b} bands are largely overlapping. Large bimolecular fluorescence quenching rates (k{sub q}{approx}10{sup 11} M{sup -1} s{sup -1}) observed from both intensity reduction and fluorescence lifetime quenching of the acceptor 9-fluorenone(9FL) in presence of the aryl-bridged donors indicate that the electron transfer (ET) radius is slightly greater than the hydrodynamic radius. The possibility of occurrence of some other fast non-radiative process along with photoinduced electron transfer whose possibility was tested by cyclic voltammetry measurements and presence was confirmed by laser flash photolysis study has been discussed. Transient absorption spectral measurements reveal that in the excited singlet (S{sub 1}) of 9FL photoinduced ET reaction is present but in its triplet (T{sub 1}) only energy transfer process is operative. Laser flash photolysis experiments provide the direct evidence for ion recombination mechanisms for production of monomeric triplets of both 9FL and the donors DIB and DIP.

Misra, T.; Maiti, M.; Saini, R.D.; Panda, S.K.; Ganguly, T

2003-01-15

40

Aryl copolymer compounds and polymer light emitting devices made by using the same  

UK PubMed Central (United Kingdom)

The present invention provides a polymer compound comprising a repeating unit of below formula (1) or (2), and a repeating unit represented by the below formula (5), and having a polystyrene reduced number average molecular weight of 10 3 to 10 8 : wherein, Ar 1 and Ar 2 each independently represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group X 1 and X 2 each independently represent O, S, C(=O), S(=O), SO 2 , C(R 1 )(R 2 ), Si(R 3 )(R 4 ), N(R 5 ), B(R 6 ), P(R 7 ) or P(=O)(R 8 ) R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, ammo group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, arylethynyl group, carboxyl group or cyano group R 1 and R 2 , or R 3 and R 4 may be connected mutually to form a ring X 1 and X 2 are not the same and wherein X 1 and Ar 2 bond to adjacent carbons in the aromatic ring of Ar 1 , and X 2 and Ar 1 bond to adjacent carbons in the aromatic ring of Ar 2 wherein, Ar 3 and Ar 4 each independently represent a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group X 3 and X 4 each independently represent N, B, P, C(R 9 ) or Si(R 10 ) R 9 and R 10 each independently represent a hydrogen atom, halogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, amide group, acid imide group, imine residue, amino group, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group, substituted silylamino group, a monovalent heterocyclic group, arylalkenyl group, arylethynyl group, carboxyl group or cyano group X 3 and X 4 are not the same and wherein X 3 and Ar 4 bond to adjacent carbons in the aromatic ring of Ar 3 , and X 4 and Ar 3 bond to adjacent carbons in the aromatic ring of Ar 4 -Ar 5 - (5) wherein Ar 5 represents an arylene group, divalent heterocyclic group, or divalent group having metal complex structure.

DOI SHUJI; KOBAYASHI SATOSHI; NOGUCHI TAKANOBU

 
 
 
 
41

Alkylation of N-substituted 2-phenylacetamides  

Directory of Open Access Journals (Sweden)

Full Text Available Various N-substituted phenylacetamides were alkylated using different alkylating agents under neutral and basic conditions. Reactions were performed at different reaction temperatures and in various solvents. Also, a number of various catalysts were used including phase-transfer catalysts. Reactions were followed using GC or GC-MS technique and the presence as well as the yields of the alkylation products were established. Generally, the best yield and high selectivity in the studied reactions were achieved under basic conditions where in the certain cases some products, mostly N-product, were obtained solely in quantitative yields.

DUSAN Z. MIJIN; MILICA M. MISIC-VUKOVIC; SLOBODAN D. PETROVIC

2004-01-01

42

Synthesis and anticonvulsant evaluation of N-substituted-isoindolinedione derivatives.  

Science.gov (United States)

A series of N-substituted-1,3-isoindolinedione derivatives (2-16) were synthesized for the purpose of defining the effect of N-substitution on the anticonvulsant activity of these derivatives. The target compounds (2-16) were obtained by condensation of phthalic anhydride with the corresponding amine derivative. The structures of the synthesized derivatives (2-16) were confirmed by means of IR, 1H-NMR, 13C-NMR, MS and elemental analyses. The anticonvulsant activity of all compounds (2-16) were evaluated by subcutaneous pentylenetetrazole seizure threshold test at doses of 0.2, 0.4 and 0.8 mmol/kg compared with sodium valproate as a positive control. Their neurotoxicity were determined by the rotorod test. Many of the present series of compounds showed good anticonvulsant activity at the tested doses, as compared to sodium valproate. Three of them (4, 6 and 11) exhibited 100% protection against convulsions, neurotoxicity and death at all tested doses. Out of the series, two compounds (12 and 13) were completely inactive with 100% mortality. 3-(p-chlorophenyl)-4-(1,3-dioxo-2,3-dihydro-1H-2-isoindolyl)butanoic acid derivative (11) has emerged as the most active compound which is 20 times more active than valproate with ED50 8.7, 169 mg/kg; TD50 413, 406 mg/kg and PI 47.5, 2.4. The results revealed the importance of the combination of baclofenic and phthalimide moieties (compound 11) as a promising anticonvulsant candidate. PMID:15202553

Abdel-Hafez, Atef Abdel-Monem

2004-05-01

43

ALPHA-AMINO-N-SUBSTITUTED AMIDES, PHARMACEUTICAL COMPOSITION CONTAINING THEM AND USES THEREOF  

UK PubMed Central (United Kingdom)

The present invention relates to filed of pharmaceutical chemistry. Disclosed are a series of +--amino-N-substituted amide compounds having a structure of the following formula, the pharmaceutically acceptable salts thereof, and the pharmaceutical composition comprising the same. The +--amino-N-substituted amide compounds or the pharmaceutically acceptable salts thereof according to the present invention have anti-tumor and/or anti-cancer activities in vivo and in vitro, can effectively depress the growth of various tumor cells and/or cancer cells, and thus can be used in preparing drugs for treating tumors and/or cancers.

NAN FAJUN; LI JIA; DING JIAN; LIU GANG; XIE CHUANMING; MIAO ZEHONG; TAI WANYI

44

Process for preparing n-substituted amine.  

UK PubMed Central (United Kingdom)

An N-substituted amine is produced by reacting an alcohol or aldehyde with ammonia, a primary amine or a secondary amine in the presence of a catalyst comprising: (a) (1) copper, (2) a metal selected from the group consisting of chromium, manganese, iron and zinc and (3) a metal of the platinum VIII group; (b) (1) copper, (2) cobalt and (3) a metal of the platinum VIII group; (c) (1) copper, (2) a metal selected from the group consisting of chromium, manganese, iron, cobalt, nickel and zinc, (3) a metal of the platinum VIII group and (4) a melal selected from the group consisting of alkali metals and alkaline earth metals; or (d) (1) copper, (2) a metal selected from the group consisting of chromium, manganese, iron, cobalt, nickel and zinc, (3) a metal of the platinum VIII group and (4) a metal selected from the group consisting of aluminum, tungsten and molybdenum. a

ABE HIROSHI; AIKAWA JUN; OKABE KAZUHIKO; SOTOYA KOHSHIRO

45

Determination of drug-polymer binding constants by affinity capillary electrophoresis for aryl propionic acid derivatives and related compounds.  

UK PubMed Central (United Kingdom)

The binding constants (K(b)s) of 17 aryl propionic acid derivatives (APADs) and related compounds with polyvinylpyrrolidone (PVP K30) and vinylpyrrolidone-vinyl acetate copolymer (Kollidon VA64) in aqueous media were determined by affinity capillary electrophoreses (ACE). The K(b)s of APAD to polymers increase with octanol-water partition coefficients of the compounds. Kollidon VA64 is a stronger binder than PVP K30 to APAD compounds. The K(b)s are greater at pH 4 than at pH 9. Both hydrophobic interaction and hydrogen bonding may be involved. However, hydrophobic interaction appears to be dominant. The ACE method is simple and fast, which could be used to study drug-polymer interaction in aqueous media.

Jia Z; Choi DS; Chokshi H

2013-03-01

46

Synthesis and characterization of some N-substituted amides of salicylic acid  

Directory of Open Access Journals (Sweden)

Full Text Available The synthesis of some N-substituted aromatic amides in the salicylic acid series was achieved, by direct reaction between primary amines and salicylic acid in inert organic solvent, in the presence of PCl3. The compounds that were obtained, partially not described in literature, were characterized by chemical-physical methods.

Lupea Xenia Alfa; Padure Mirabela

2003-01-01

47

Magnesium-induced copper-catalyzed synthesis of unsymmetrical diaryl chalcogenide compounds from aryl iodide via cleavage of the Se-Se or S-S bond.  

UK PubMed Central (United Kingdom)

The methodology for a copper-catalyzed preparation of diaryl chalcogenide compounds from aryl iodides and diphenyl dichalcogenide molecules is reported. Unsymmetrical diaryl sulfide or diaryl selenide can be synthesized from aryl iodide and PhYYPh (Y = S, Se) with a copper catalyst (CuI or Cu(2)O) and magnesium metal in one pot. This reaction can be carried out under neutral conditions according to an addition of magnesium metal as the reductive reagent. Furthermore, it is efficiently available for two monophenylchalcogenide groups generated from diphenyl dichalcogenide.

Taniguchi N; Onami T

2004-02-01

48

Magnesium-induced copper-catalyzed synthesis of unsymmetrical diaryl chalcogenide compounds from aryl iodide via cleavage of the Se-Se or S-S bond.  

Science.gov (United States)

The methodology for a copper-catalyzed preparation of diaryl chalcogenide compounds from aryl iodides and diphenyl dichalcogenide molecules is reported. Unsymmetrical diaryl sulfide or diaryl selenide can be synthesized from aryl iodide and PhYYPh (Y = S, Se) with a copper catalyst (CuI or Cu(2)O) and magnesium metal in one pot. This reaction can be carried out under neutral conditions according to an addition of magnesium metal as the reductive reagent. Furthermore, it is efficiently available for two monophenylchalcogenide groups generated from diphenyl dichalcogenide. PMID:14750822

Taniguchi, Nobukazu; Onami, Tetsuo

2004-02-01

49

New N-substituted oxazolidine derivatives useful for preparing hydroxyalkylamino and polymeric hydroxyalkylamino derivatives for manufacturing e.g. high-performance composite materials for parts of automotives and electronics  

UK PubMed Central (United Kingdom)

N-Substituted oxazolidine derivatives (I) are new. N-Substituted oxazolidine derivatives of formula (I) are new. R3 : -H, -1-8C alkyl or 6-15C aryl R6 : CH 2-CHR1-O-CO-1-8C-alkyl, -CH 2-CHR1-O-CO-CR5=CH 2, -CH 2-CHR1-O-CO-NH-1-8C-alkyl, -CH 2-CHR1-O-CO-NH-6-15C-aryl, -CO-O-1-8C-alkyl, -CO-CR5=CH 2, -CO-O-phenyl, -CO-NH-1-8C-alkyl, -CO-NH-6-15C-aryl, -CH 2-CHR1-O-CO-CH 2-CO-CH 3, -CH 2-CHR1-O-CO-CH 2-CO-O-1-12C-alkyl and R1, R5 : 1-8C alkyl or H. Independent claims are included for: (1) the preparation of (I) (2) hydroxyalkylamino derivatives of formula (Y1-[A] m) (III) (3) the preparation of (III) comprising (d) reacting the N-substituted oxazolidine derivative with a compound (A) comprising urea, di-alkylurea, triazines such as melamine, melam, substituted melamine, preferably succinimidomelamine, phthalimidomelamine, alkylated melamine (preferably N,N-dimethylmelamine) or ammeline, guanamines such as benzoguanamine or acetoguanamine, and amides, preferably bi- or polyfunctional polyamides, polyureas and polyurethanes and phenols, preferably ortho- or para-substituted phenols, bisphenol and novolac, preferably novolac from ortho- or para-substituted phenols (4) N-substituted bisoxazolidine derivatives of formula (IV) (5) the preparation of (IV) comprising (a) reacting alkanolamine compounds of formula (HN-(CH 2 CHR1-OH) 2) (A) or (HNR2-CH 2-CHR1-OH) (B) with an aldehyde of formula (HC(R3)=O) (b) dehydrating formed methylol derivatives to give an oxazolidine derivative of formula (II) and (c1) reacting (II) with bifunctional compounds containing bifunctional dicarboxylic groups of formula (1-4C alkyl-O-CO-1-8C alkyl-CO-O-1-4C alkyl), (1-4C alkyl-O-CO-6-15C-aryl-CO-O-1-4C alkyl), (1-4C alkyl-O-CO-CH=CH-CO-O-1-4 alkyl) or their anhydrides, diisocyanates of formula (OCN-1-8C alkyl-NCO) or (OCN-6-15C-aryl-NCO), or organic carbonates of formula (1-4C alkyl-O-CO-O-1-4C alkyl), (1-4C alkyl-O-CO-O-phenyl), (phenyl-O-CO-O-phenyl) to give (IV) (6) polymeric hydroxyalkylamino derivatives of formula ([-Y1-B1-] p) (XIII) (7) the preparation of (XIII) comprising (d1) reacting the N-substituted bisoxazolidine derivative with a compound (A), where the amide is preferably polyamides, polyureas and polyurethanes (8) a mixture comprising at least one derivative (III) and/or at least a derivative (XIII) and at least one additive comprising UV stabilizers in the form of radical stabilizers and/or UV absorbers, fillers, reinforcing fibers and/or radical initiators and (9) the use of (III) and/or (XIII) and the mixture for manufacturing crosslinked semifinished products, molding materials or high-performance composite materials for highly stressed parts in automotives, mechanical engineering, electrical engineering and electronics. In formula (III), A : -CHR3-NR15-CH 2-CHR1-OR16 Y1 : hydroxy phenyl group of formula (a)-(d), triazine group of formula (e)-(h), (-N12-CO-NR12) (i), ((-C(O)-NX-R8-) m) (j), ((-O-C(O)-NX-R8-) m) (k) or ((-NX-C(O)-NX-R8-) m) (l) R1, R3, R5 : 1-8C alkyl or H R8 : 1-8C alkyl or 6-15C-aryl R10 : 1-3C-alkyl R11 : H, 1-4C alkyl, C 6H 5, C 6H 4-OH or 1-3C-alkyl-C 6H 4OH R12 : H, 1-4C alkyl, 6-15C-aryl or -CHR3-NR15-CH 2CHR1-OR16 R13 : 1-8C alkyl, C 6H 5 or heterocyclic groups (A13) comprising pyrrolidine-2,5-dion-1-yl group of formula (m), pyrrolidine-2,5-dion-1-yl, 3-methylene-pyrrolidine-2,5-dion-1-yl, piperidine-2,6-dion-1-yl, hexahydro-isoindole-1,3-dion-2-yl, decahydro-benzo[f]isoindole-1,3-dion-2-yl, isoindole-1,3-dion-2-yl or benzo[f]isoindole-1,3-dion-2-yl R14 : 1-8C alkyl or 6-15C-aryl R15 : H, 1-4C alkyl, 6-15C-aryl or -CH 2-CHR1-OR16 R16 : H, 1-8C-alkyl, -CO-NH-(1-18C alkyl), -CO-CR5=CH 2, -CO-O-1-4C alkyl, -CO-O-6-15C-aryl, -CO-CH 2-CO-CH 3, -CO-CH 2-CO-O-(1-12C-alkyl) or -Si(1-8C alkyl) 3 R17 : 1-12C-alkyl or -CH=CH-1-10C alkyl X : A or H and m, o : 1-30, where the linkage between the units A and Y1 takes place by at least one N atom, when Y1 unit contains a N-atom substituent, the linkage is in ortho and/or para-position to the hydroxyl group of the hydroxyaromatics, when the Y1 unit includes a hydroxyaromatic

RAETZSCH MANFRED; MEINECKE ANDREAS

50

Synthesis and cytotoxic evaluation of novel N-substituted amidino-1-hydroxybenzimidazole derivatives.  

UK PubMed Central (United Kingdom)

A new class of N-substituted amidino-1-hydroxybenzimidazole derivatives (15-24) were synthesized and evaluated for their in vitro cytotoxic activities against human leukemia cell lines, HL-60 and K562. The preliminary results showed that compounds 16, 20, 21 and 23 had moderate antitumor activity against HL-60 cell line. Further investigation on the mechanism of the observed cytotoxic effects demonstrated that compound 21 increased the expression of autophagic and apoptotic genes and induced apoptosis of HL-60 cells.

Alp M; Göker H; Ozkan T; Sunguroglu A

2013-07-01

51

METHOD OF PRODUCING N-SUBSTITUTED BIS[DIALKOXYPHOSPHORYL]ACETAMIDINES  

UK PubMed Central (United Kingdom)

FIELD: chemistry. ^ SUBSTANCE: invention relates to a method of producing N-substituted bis[dialkoxyphosphoryl]acetamidines, which can be used to produce biologically active compounds of formula: where R1 = i-C3H7, C4H9 R2=CH3, C3H5 X=-N(C2H5)2, -N(C3H7)2, -N(C4H9)2 -N(CH2CH2)2O. The disclosed method involves reaction of C-phosphorylated acetamidines of formula where R1=i-C3H7, C4H9 X=-N(C2H5)2, -N(C3H7)2, -N(C4H9)2 -N(CH2CH2)2O, with sodium with subsequent phosphorylation of the obtained derivative with dimethylchlorophosphate or diethylchlorophosphate in dioxane in molar ratio C-phosphorylated acetamidine: sodium: dialkylchlorophosphate equal to 1:1:1:1.05 and temperature 20-50C. ^ EFFECT: efficient novel method of obtaining the said compound. ^ 1 cl, 5 ex

SHISHKIN VENIAMIN EVGEN EVICH; POPOV JURIJ VASIL EVICH; MEDNIKOV EVGENIJ VIKTOROVICH; ANISHCHENKO OKSANA VITAL EVNA; SHEVCHENKO MARIJA ALEKSANDROVNA; GURBA EVGENIJA VIKTOROVNA

52

Group IB Organometallic Chemistry XIX.Synthesis and characterization of mixed-organocopper cluster compounds R4R'2Cu6 containing aryl and acetylide ligands.  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Mixed-organocopper cluster compounds Ar4Cu6(CCR)2 (Ar = 2-Me2NC6H4, R = phenyl, 4-tolyl, 2,4-xylyl or mesityl) have been prepared in high yield by the ligand-substitution reaction of Ar4Cu6Br2 with two equivalents of LiCCR. Ar4Cu6(CCC6H4CH3-4)2 has also been prepared via the aryl¡ªarylacetylide exch...

Koten, G. van; Hoedt, R.W.M. ten; Noltes, J.G.

53

SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL SCREENING OF VARIOUS N-SUBSTITUTED DERIVATIVES OF SULFONAMIDES  

Directory of Open Access Journals (Sweden)

Full Text Available In the present study, a series of N-substituted sulfonamides have been synthesized. The reaction ofbenzene sulfonyl chloride (1) with O-anisidine (2) yielded N-(2-methoxyphenyl) benzenesulfonamide (3), which onbromination with bromine in the presence of acetic acid gave N-(4,5-dibromo-2-methoxyphenyl)benzenesulfonamide(6). The two products (3) and (6) further on treatment with alkyl halides/acyl halide in the presence of sodium hydrideyielded thirteen different N-substituted sulfonamides. The compounds were characterized by IR, EIMS and 1H-NMRand screened against acetyl cholinesterase, butyryl cholinesterase and lipoxygenase enzymes. The results revealedthat N-butyl-N-(4, 5-dibromo-2-methoxyphenyl)benzene sulfonamide (6d) and N-pentyl-N-(4,5-dibromo-2-methoxyphenyl)benzenesulfonamide (6e) exhibited good inhibitory potential against lipoxygenase.

AZIZ-UR-REHMAN, WAJEEHA TANVEER, MUHAMMAD ATHAR ABBASI, SUMBAL AFROZ, KHALID MOHAMMED KHAN, MUHAMMAD ASHRAF, AND IFTIKHAR AFZAL

2011-01-01

54

Synthesis of N-substituted C-normorphinans and their pharmacological properties.  

UK PubMed Central (United Kingdom)

Several N-substituted C-normorphinans (VIII and IX) were synthesized and tested for their analgetic and narcotic antagonist activities and physical dependence capacity. Treatment of N-formyl- octahydro-2-pyrindine (IIIc) with polyphosphoric acid readily gave N-formyl-C-normorphinan (IV). The N-nor bases (V and VII) obtained from IV were converted to VIII and IX. The N-methyl derivative (I), which was previously reported to be inactive by Haffner's method, exhibited potent analgetic activity by the hot plate method and the AcOH-induced writhing test. Compounds VIII and IX showed pharmacological properties similar to those of N-substituted morphinans and exhibited agonist (analgetic) and/or narcotic antagonist activities. The C-nor analogue (IXa) of cyclorphan (IIc) exhibited potent analgetic and antagonist activities with no physical dependence capacity in the single-dose suppression tests both in rats and monkeys.

Takeda M; Inoue H; Noguchi K; Honma Y; Okamura K; Date T; Nurimoto S; Yamamura M; Saito S

1992-05-01

55

Synthesis of N-substituted C-normorphinans and their pharmacological properties.  

Science.gov (United States)

Several N-substituted C-normorphinans (VIII and IX) were synthesized and tested for their analgetic and narcotic antagonist activities and physical dependence capacity. Treatment of N-formyl- octahydro-2-pyrindine (IIIc) with polyphosphoric acid readily gave N-formyl-C-normorphinan (IV). The N-nor bases (V and VII) obtained from IV were converted to VIII and IX. The N-methyl derivative (I), which was previously reported to be inactive by Haffner's method, exhibited potent analgetic activity by the hot plate method and the AcOH-induced writhing test. Compounds VIII and IX showed pharmacological properties similar to those of N-substituted morphinans and exhibited agonist (analgetic) and/or narcotic antagonist activities. The C-nor analogue (IXa) of cyclorphan (IIc) exhibited potent analgetic and antagonist activities with no physical dependence capacity in the single-dose suppression tests both in rats and monkeys. PMID:1394632

Takeda, M; Inoue, H; Noguchi, K; Honma, Y; Okamura, K; Date, T; Nurimoto, S; Yamamura, M; Saito, S

1992-05-01

56

METHOD FOR PRODUCTION OF N-SUBSTITUTED MALEIMIDES  

UK PubMed Central (United Kingdom)

A method for manufacturing N-substituted maleimides is provided to inhibit the cause of side reaction during the synthesis process by using supported catalyst. A method for manufacturing N-substituted maleimides comprises a step of adding primary amine and anhydrous maleic acid under the presence of supported catalyst to synthesize the N-substituted maleimides in which an organic phosphonic acid is supported in solid carrier. The synthesis temperature is 100-140 DEG C. The organic phosphonic acid is insoluble with N-substituted maleimide and, whose melting point is over 150 DEG C. The organic phosphonic acid is selected from 2-phosphonobutane-1,2,4-tricarboxyl acid, 2-hydroxy phosphonoacetic acid, amino trimethylene phosphonic acid, 1-hydroxyethylidene-1, 1-diphosphonic acid, bishexamethylene triamine pentamethylene phosphonic acid, ethylenediamine tetramethylene phosphonic acid and diethylen triamine penta methylene phosphonic acid. The solid carrier is selected from diatomite, zirconium oxide yttrium oxide lineage ceramics, silica, silica-alumina, titanium dioxide, activated carbon, clay and montmorillonite.

OH HYUN TAEK; LEE HYUNG SUB; KIM JONG BEOM; SEO HYE WON

57

Synthesis and cytotoxic activity of N-substituted thiosemicarbazones of 3-(3,4-methylenedioxy)phenylpropanal.  

Science.gov (United States)

Five new N-substituted thiosemicarbazones of 3-(3,4-methylenedioxy)phenylpropanal were synthesized. Safrole, a natural product obtained from sassafras oil (Ocotea pretiosa), was oxidized to alcohol using BH3-THF and H2O2, followed by oxidation to aldehyde using pyridinium dichromate (PDC) and condensation with five N-substituted derivatives of thiosemicarbazide. Tests were performed to evaluate the cytotoxic activity with continuous chain KB cells (epidermoide carcinoma of the floor of the mouth). Compounds 5 and 6 showed IC50 values of 1.5 and 4.6 micrograms/ml, respectively. PMID:9639871

Joselice e Silva, M; Alves, A J; Do Nascimento, S C

1998-03-01

58

Synthesis and cytotoxic activity of N-substituted thiosemicarbazones of 3-(3,4-methylenedioxy)phenylpropanal.  

UK PubMed Central (United Kingdom)

Five new N-substituted thiosemicarbazones of 3-(3,4-methylenedioxy)phenylpropanal were synthesized. Safrole, a natural product obtained from sassafras oil (Ocotea pretiosa), was oxidized to alcohol using BH3-THF and H2O2, followed by oxidation to aldehyde using pyridinium dichromate (PDC) and condensation with five N-substituted derivatives of thiosemicarbazide. Tests were performed to evaluate the cytotoxic activity with continuous chain KB cells (epidermoide carcinoma of the floor of the mouth). Compounds 5 and 6 showed IC50 values of 1.5 and 4.6 micrograms/ml, respectively.

Joselice e Silva M; Alves AJ; Do Nascimento SC

1998-03-01

59

Synthesis and crystal structure of N-(3-benzylamino-2- cyano-3-methylthioacrylyl)-N'-(substituted phenyl)ureas  

Directory of Open Access Journals (Sweden)

Full Text Available Phenylurea groups were introduced into the frame of traditional cyanoacrylate and a series of N-(3-benzylamino-2-cyano-3-methylthioacrylyl)-N'-(substituted phenyl)ureas were synthesized. All compounds are new and their structures were confirmed by 1H NMR, 13C NMR and mass spectral analyses.

S.H. Zhong; M.L. Fan; B.Y. Liu; D.M. Wei; J.B. Liu

2013-01-01

60

Synthesis, characterization and dynamic NMR studies of a novel chalcone based N-substituted morpholine derivative  

Science.gov (United States)

The synthesis of a novel chalcone based N-substituted morpholine derivative namely, (E)-1-(biphenyl-4-yl)-3-(4-(5-morpholinopentyloxy) phenyl) prop-2-en-1-one (BMPP), using a two step protocol is reported. The compound is characterized by FTIR, GC-MS and FTNMR spectroscopy techniques. Advanced 2D NMR techniques such as gradient enhanced COSY, HSQC, HMBC and NOESY were employed to establish through-bond and through-space correlations. Dynamic NMR measurements were carried out to obtain the energy barrier to ring inversion of the morpholine moiety.

Baskar, R.; Baby, C.; Moni, M. S.; Subramanian, K.

2013-05-01

 
 
 
 
61

Method for oxidative cleavage of substituted vinylaromatics, involves oxidizing aryl vinyl compounds in presence of molecular oxygen to aldehydes or ketones, where enzyme is used as catalyst  

UK PubMed Central (United Kingdom)

Oxidative cleavage involves oxidizing aryl vinyl compounds in presence of molecular oxygen to aldehydes or ketones, where an enzyme is used as a catalyst. The enzyme is selected from fungal peroxidases and laccases, halogen peroxidase, lignin peroxidase, horseradish peroxidase and cattle milk peroxidase. The oxidation is carried out in a bis-tris buffer, acetate buffer, formate buffer or phosphate buffer under oxygen pressure, preferably an organic solvent. The aryl vinyl compounds having general formula (I), and aldehyde having general formula (II), preferably vanillin, and ketone having general formula (III). n : 0-5 R 1>saturated or unsaturated hydrocarbon with 1-10C, which are replaced by heteroatoms and further substituted, amino, 1-6C alkylamino, 1-6C dialkylamino, halogens, hydroxy or cyano, where two of the substituents R 1> are joined to form a ring and R 2> and R 3>independent of one another, H or one of the options for R 1>, where R 2> or R 3> are joined to an R 1> to form a ring. [Image] [Image] [Image

KROUTIL WOLFGANG; LARA MIGUEL

62

Synthesis and biological activity of 3-N-substituted estrogen derivatives as breast cancer agents.  

UK PubMed Central (United Kingdom)

3-N-substituted-estrogen derivatives were synthesized and characterized. Their antiproliferative activities against human ER (+) MCF-7 (Breast), ER (-) MDA-MB-231 (breast) and Ishikawa (endometrial) cancer cell lines were determined after 72 hours drug exposure employing CellTiter-Glo assay at concentrations ranging from (0.01-100,000 nM). The antiproliferative activities of these compounds were compared to tamoxifen (TAM), 4-hydroxytamoxifen (4-OHT, active metabolite of tamoxifen) and raloxifene (RAL). In vitro results indicated that compound 5 (IC50 = 12 µM) displayed comparable antiproliferative activity against MDA-MB 231 cell line; while compounds 6, 7 and 13 (IC50 = 12 µM) displayed higher activity against MCF-7 and Ishikawa cell lines, in comparison to TAM activity (19-33 µM).

Wan Z; Musa MA; Joseph P; Cooperwood JS

2013-07-01

63

Design & synthesis of N'-[substituted] pyridine-4-carbohydrazides as potential anticonvulsant agents.  

Science.gov (United States)

A series of N'-[substituted] pyridine-4-carbohydrazides were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity of the titled compounds was established after intraperitoneal administration in three seizure models, which include MES, scMET and 6 Hz model. The most active compound of the series was N'-[4-(4-fluorophenoxy)benzylidene]pyridine-4-carbohydrazide PCH 6, which showed a MES ED50 value of 128.3 mg/kg and 6 Hz ED50 value of 53.3 mg/kg in mice. The median toxic dose (TD50) was 343.6 mg/kg, providing compound PCH 6 with a protection index of 2.67 in the MES test and 6.44 in 6 Hz test. A computational study was also carried out, including calculation of pharmacophore pattern, prediction of pharmacokinetic properties and docking studies. PMID:21167624

Tripathi, Laxmi; Singh, Ranjit; Stables, James P

2010-11-24

64

Design & synthesis of N'-[substituted] pyridine-4-carbohydrazides as potential anticonvulsant agents.  

UK PubMed Central (United Kingdom)

A series of N'-[substituted] pyridine-4-carbohydrazides were designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity of the titled compounds was established after intraperitoneal administration in three seizure models, which include MES, scMET and 6 Hz model. The most active compound of the series was N'-[4-(4-fluorophenoxy)benzylidene]pyridine-4-carbohydrazide PCH 6, which showed a MES ED50 value of 128.3 mg/kg and 6 Hz ED50 value of 53.3 mg/kg in mice. The median toxic dose (TD50) was 343.6 mg/kg, providing compound PCH 6 with a protection index of 2.67 in the MES test and 6.44 in 6 Hz test. A computational study was also carried out, including calculation of pharmacophore pattern, prediction of pharmacokinetic properties and docking studies.

Tripathi L; Singh R; Stables JP

2011-02-01

65

Insecticidal N-substituted (6-haloalkylpyridin-3-yl)alkyl sulfoximines  

UK PubMed Central (United Kingdom)

Disclosed are N-substituted (6-haloalkylpyridin-3-yl)alkyl sulfoximine compounds as represented by formula (I), wherein X represents NO2, CN or COOR4 L represents a single bond, or R1, S and L taken together represents a 4-, 5- or 6-membered ring R1 represents alkyl R2 and R3 independently represent hydrogen, alkyl, fluoro, chloro or bromo n is an integer from 0-3 Y represents haloalkyl and R4 represents alkyl. Of particular importance is the compound [1-(6-trifluoromethylpyridin-3-yl)ethyl](methyl)-oxido-l4-sulfanylidenecyanamide. Further disclosed is a composition for controlling insects which comprises a compound as defined above and one or more insecticides, fungicides or herbicides such as methoxyfenozide, spinosad, spinetoram, imidacloprid, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, bifenthrin, clothianidin, zeta-cypermethrin, lambda-cyhalothrin, rynaxypyr and spirotetramat.

LOSO MICHAEL R; NUGENT BENJAMIN M; HUANG JIM X; ROGERS RICHARD B; ZHU YUANMING; RENGA JAMES M; HEGDE VIDYADHAR B; DEMARK JOSEPH J

66

6-Aryl-4,5-dihydro-3(2H)-pyridazinones. A new class of compounds with platelet aggregation inhibiting and hypotensive activities.  

UK PubMed Central (United Kingdom)

This paper reports on the synthesis and pharmacological activity of 6-aryl-4,5-dihydro-3(2H)-pyridazinone derivatives. The compounds exhibit an aggregation inhibiting action on human platelets in vitro and on rat platelets under ex vivo conditions, as well as a hypotensive action on rats. The strongest pharmacological effects were found with dihydropyridazinones, which have a 6-[p-[(chloroalkanoyl)amino]phenyl] substituent, together with a methyl group in the 5-position. The antiaggregation activity of compounds of this type is in vitro up to 16000 times and ex vivo up to 370 times greater than that of acetylsalicylic acid; the hypotensive action is up to 40 times as great as that of the comparative substance dihydralazine.

Thyes M; Lehmann HD; Gries J; König H; Kretzschmar R; Kunze J; Lebkücher R; Lenke D

1983-06-01

67

Intermolecular enantioselective Heck-Matsuda arylations of acyclic olefins: application to the synthesis of ?-aryl-?-lactones and ?-aryl aldehydes.  

UK PubMed Central (United Kingdom)

We describe herein a synthetically useful method for the enantioselective intermolecular Heck-Matsuda arylation of acyclic allylic alcohols. Aryldiazonium tetrafluoroborates were applied as arylating agents in the presence of Pd(TFA)2 and a chiral, commercially available, bisoxazoline ligand. The methodology is straightforward, robust, scalable up to a few grams, and of broad scope allowing the synthesis of a range of ?-aryl-carbonyl compounds in good to high enantioselectivities and yields. This new enantioselective Heck-Matsuda arylation allowed the synthesis of ?-aryl-?-lactones and ?-aryl aldehydes, which play a vital role as key intermediates in the synthesis of the biologically active compounds, such as (R)-baclofen, (R)-rolipram, (S)-curcumene, (S)-dehydrocurcumene, and (S)-tumerone.

Oliveira CC; Angnes RA; Correia CR

2013-05-01

68

Hybrid analogues of SFTI-1 modified in P1 position by ?- and ?-amino acids and N-substituted ?-alanines.  

UK PubMed Central (United Kingdom)

A series of compounds containing either non-proteinogenic ?-/?-amino acids or N-substituted ?-alanine residues (?-peptoid units) in P1 specificity position were synthesized based on the structure of sunflower trypsin inhibitor 1 (SFTI-1). The compounds were synthesized on a solid support; the N-substituted ?-alanines (?Nhlys and ?Nhphe) were introduced into a peptidomimetic chain via a two-step approach using acryloyl chloride and an appropriate primary amine. The inhibitory activities were characterized in vitro against bovine ?-chymotrypsin or bovine ?-trypsin. Three analogues displayed activity comparable to fully proteinogenic counterparts-monocyclic SFTI-1 and [Phe(5) ]SFTI-1. Moreover, all active peptidomimetics were resistant toward proteolytic degradation, even after 24-h incubation at room temperature. © 2012 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 100: 154-159, 2013.

Debowski D; Lukajtis R; Filipowicz M; Strzelecka P; Wysocka M; L?gowska A; Lesner A; Rolka K

2013-04-01

69

Synthesis, characterization and biological screening of N-substituted derivatives of 5-benzyl-1,3,4-oxadiazole-2yl-2"-sulfanyl acetamide.  

UK PubMed Central (United Kingdom)

A series of new N-substituted derivatives of 5-benzyl-1, 3, 4-oxadiazole-2yl-2"-sulfanyl acetamide (6a-n) were synthesized in three phases. The first phase involved the sequentially converting phenyl acetic acid into ester, hydrazide and finally cyclized in the presence of CS2 to afford 5-benzyl-1, 3, 4-oxadiazole-2-thiol. In the second phase N-substituted-2-bromoacetamides were prepared by reacting substituted amines with bromoacetyl bromide in basic media. In the third phase, 5-benzyl-1,3,4-oxadiazole-2-thiol was stirred with N-substituted-2-bromoacetamides in the presence of N,N-dimethyl formamide (DMF) and sodium hydride (NaH) to get the target compounds. Spectral techniques were used to confirm the structures of synthesized compounds. Synthesized compounds were screened against butyrylcho linesterase (BChE), acetylcholinesterase (AChE), and lipoxygenase enzymes (LOX) and were found to be relatively more active against acetylcholinesterase.

Siddiqui SZ; Rehman A; Abbasi MA; Abbas N; Khan KM; Ashraf M; Ejaz SA

2013-05-01

70

Identification of N-substituted 8-azatetrahydroquinolone derivatives as selective and orally active M(1) and M(4) muscarinic acetylcholine receptors agonists.  

Science.gov (United States)

We designed and synthesized N-substituted 8-azatetrahydroquinolone derivatives as selective M1 and M4 muscarinic acetylcholine receptors agonists. Optimization of selected derivatives led to the discovery of compound 7 as a highly potent M1 and M4 agonist with weak hERG inhibition. Oral administration of compound 7 improved psychosis-like behavior in rats. PMID:23816371

Takai, Kentaro; Inoue, Yasunao; Konishi, Yasuko; Suwa, Atsushi; Uruno, Yoshiharu; Matsuda, Harumi; Nakako, Tomokazu; Sakai, Mutsuko; Nishikawa, Hiroyuki; Hashimoto, Gakuji; Enomoto, Takeshi; Kitamura, Atsushi; Uematsu, Yasuaki; Kiyoshi, Akihiko; Sumiyoshi, Takaaki

2013-06-13

71

The cleavage of the aryl-O-CH/sub 3/ bond using anisole as a model compound  

Energy Technology Data Exchange (ETDEWEB)

The thermal decomposition of anisole as a prototype of the aryl-methyl-ether linkage of lignin and coals has been studied under supercritical conditions using tetralin as hydrogen donor solvent. The effect of homogenous Lewis acid catalysts have also been studied under the same conditions. The main reaction products are phenol, benzene, toluene and cresols. At high tetralin to anisole ratios the selectivity to phenol is almost 80% with little or no cresol production. This selective conversion can be carried out rapidly and cleanly at high temperature (>450 degrees C). Kinetic studies were undertaken using pyrolytic, donor solvent hydrogenolytic and Lewis acid catalysed regimes in the temperature range 400-500 degrees C. The kinetics of anisole decomposition in a large excess of tetralin have been found to be in good agreement with those published in the literature. The Lewis acid catalysts lower the activation energy relative to the pyrolytic and hydrogenolytic cases. The kinetic studies and their mechanistic interpretation lead to a mechanism involving surprisingly few radical species: methyl, phenoxy, phenoxymethyl and phenyl radicals. In the presence of FeCl/sub 3/, the selectivity towards phenols and cresols is enhanced, though a side reaction leads to polymerization at low (400-420 degrees C) temperatures. It is concluded that the aryl-O-methyl ether linkage in anisole can easily be broken at high temperatures, 450-500 degrees C, in supercritical hydrogen donor solvent to give phenol in high yield and selectivity. 23 refs., 4 figs., 5 tabs.

Afifi, A.I.; Hindermann, J.P.; Chornet, E.; Overend, R.P.

1989-04-01

72

Catalyst-controlled divergent C-h functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds with alkynes and alkenes.  

UK PubMed Central (United Kingdom)

Achieving site-selective, switchable C-H functionalizations of substrates that contain several different types of reactive C-H bonds is an attractive objective to enable the generation of different products from the same starting materials. Herein, we demonstrate the divergent C-H functionalization of unsymmetrical 2-aryl cyclic 1,3-dicarbonyl compounds that contain two distinct, nonadjacent sites for initial C-H functionalization, where product selectivity is achieved through catalyst control. By use of a palladium-N-heterocyclic carbene complex as the precatalyst, these substrates undergo oxidative annulation with alkynes to provide spiroindenes exclusively. In contrast, a ruthenium-based catalyst system gives benzopyrans as the major products. Examples of divergent, oxidative C-H alkenylations of the same substrates are also provided.

Dooley JD; Reddy Chidipudi S; Lam HW

2013-07-01

73

N-substituted carbamates and their use as gasoline additives.  

UK PubMed Central (United Kingdom)

The invention provides polyolefin-polyamine-N-substituted polycarbamates, useful for preventing or reducing deposits in engines, of the general formula: wherein n is 2 to 8; R<1> represents a polyolefin chain having a number average molecular weight (Mn) in the range from 500 to 9900; each R<2> independently represents a C2-C8 alkylene group; R<3> represents a hydrogen atom or a C1-C7 alkyl group; each R<4> independently represents a hydrogen atom, a C1-C7 alkyl group, or -COOR<5> with at least two of R<4> being -COOR<5> and wherein each R<5> independently represents a hydrocarbyl or substituted hydrocarbyl group containing up to 20 carbon atoms; a process for their preparation; and gasoline compositions and gasoline additive concentrates containing them.

JOHNSON THOMAS HOWARD

74

Synthesis, Characterization and Antimicrobial Activity of 2-hydroxy-5-bromo-4- methoxy-N-(substituted phenyl) chalconeimine  

Directory of Open Access Journals (Sweden)

Full Text Available A series of 2-hydroxy-5-bromo-4-methoxy-N-(substituted phenyl) chalconeimine was synthesized,characterized and tested for their antimicrobial activity. These new derivative was achieved by treating2-hydroxy-5-bromo-4-methoxy chalcone with substituted aniline at reflux temperature using ethanol assolvent in presence of H2SO4. Structures of the synthesized compounds were characterized using IR, 1HNMRand mass spectroscopy. The synthesized compounds were screened for their in vitro antibacterialactivity against bacteria S. aureus, E. coli, P. aeruginosa and S. Pyogenes. And antifungal activityagainst C. Albicans and A.Clavatus some of these compounds exhibited moderate to good activity.

Patil S; Utale P; Gholse S; Pande S; Thakur S

2013-01-01

75

Predicting the sensitivity of fishes to dioxin-like compounds: possible role of the aryl hydrocarbon receptor (AhR) ligand binding domain.  

UK PubMed Central (United Kingdom)

Dioxin-like compounds are chronically toxic to most vertebrates. However, dramatic differences in sensitivity to these chemicals exist both within and among vertebrate classes. A recent study found that in birds, critical amino acid residues in the aryl hydrocarbon receptor (AhR) ligand binding domain are predictive of sensitivity to dioxin-like compounds in a range of species. It is currently unclear whether similar predictive relationships exist for fishes, a group of animals at risk of exposure to dioxin-like compounds. Effects of dioxin-like compounds are mediated through the AhR in fishes and birds. However, AhR dynamics are more complex among fishes. Fishes possess AhRs that can be grouped within at least three distinct clades (AhR1, AhR2, AhR3) with each clade possibly containing multiple isoforms. AhR2 has been shown to be the active form in most teleosts, with AhR1 not binding dioxin-like compounds. The role of AhR3 in dioxin-like toxicity has not been established to date and this clade is only known to be expressed in some cartilaginous fishes. Furthermore, multiple mechanisms of sensitivity to dioxin-like compounds that are not relevant in birds could exist among fishes. Although, at this time, deficiencies exist for the development of such a predictive relationship for application to fishes, successfully establishing such relationships would offer a substantial improvement in assessment of risks of dioxin-like compounds for this class of vertebrates. Elucidation of such relationships would provide a mechanistic foundation for extrapolation among species to allow the identification of the most sensitive fishes, with the ultimate goal of the prediction of risk posed to endangered species that are not easily studied.

Doering JA; Giesy JP; Wiseman S; Hecker M

2013-03-01

76

Green chemistry approach to the synthesis of N-substituted piperidones.  

UK PubMed Central (United Kingdom)

An efficient green chemistry approach to the synthesis of N-substituted piperidones and piperidines was developed and applied to the synthesis of 1-(2-pyridinylmethyl)-piperidin-4-one, 1, a key starting material for the synthesis of LY317615, an antiangiogenic agent currently under development at Eli Lilly and Company (Chart 1).(1) The general utility of this methodology, which presents significant advantages over the classical Dieckman approach to this class of compounds, was also demonstrated by the direct synthesis of a series of substituted piperidones and piperidines, including potential dopamine D4 receptor antagonists 2 and 3, that have been evaluated in the clinic as antipsychotic agents (Chart 2).(2)

Faul MM; Kobierski ME; Kopach ME

2003-07-01

77

Lewis acid free high speed synthesis of nimesulide-based novel N-substituted cyclic imides  

Scientific Electronic Library Online (English)

Full Text Available Abstract in portuguese A primeira síntese de novas imidas cíclicas derivadas de nimessulida foi realizada via reação de uma imina preparada a partir de nimessulida com anidridos apropriados na presença de acetato de sódio. Usando este processo, uma variedade de imidas cíclicas N-substituídas foi preparada em bons rendimentos em ácido acético glacial. Alguns dos compostos sintetizados mostraram atividades anti-inflamatórias quando testados in vivo. Abstract in english The first synthesis of nimesulide-based novel cyclic imides has been accomplished via the reaction of an amine prepared from nimesulide with appropriate anhydrides in the presence of sodium acetate. Using this process a variety of N-substituted cyclic imides was prepared in good yields in glacial acetic acid. Some of the compounds synthesized showed anti-inflammatory activities when tested in vivo.

Kankanala, Kavitha; Reddy, Vangala Ranga; Mukkanti, Khagga; Pal, Sarbani

2010-01-01

78

4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.  

Science.gov (United States)

A series of 4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides were designed and synthesised. Their binding potencies as inhibitors of selected recombinant human carbonic anhydrase (hCA) isozymes I, II, VII, and XIII were measured using isothermal titration calorimetry and the thermal shift assay. To determine the structural features of inhibitor binding, the crystal structures of several compounds in complex with hCA II were determined. Several compounds exhibited selectivity towards isozymes I, II, and XIII, and some were potent inhibitors of hCA VII. PMID:20889345

S?džius, Jurgis; Baranauskien?, Lina; Golovenko, Dmitrij; Matulien?, Jurgita; Michailovien?, Vilma; Torresan, Jolanta; Jachno, Jelena; Sukackait?, Rasa; Manakova, Elena; Gražulis, Saulius; Tumkevi?ius, Sigitas; Matulis, Daumantas

2010-09-08

79

4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides as inhibitors of carbonic anhydrase isozymes I, II, VII, and XIII.  

UK PubMed Central (United Kingdom)

A series of 4-[N-(substituted 4-pyrimidinyl)amino]benzenesulfonamides were designed and synthesised. Their binding potencies as inhibitors of selected recombinant human carbonic anhydrase (hCA) isozymes I, II, VII, and XIII were measured using isothermal titration calorimetry and the thermal shift assay. To determine the structural features of inhibitor binding, the crystal structures of several compounds in complex with hCA II were determined. Several compounds exhibited selectivity towards isozymes I, II, and XIII, and some were potent inhibitors of hCA VII.

S?džius J; Baranauskien? L; Golovenko D; Matulien? J; Michailovien? V; Torresan J; Jachno J; Sukackait? R; Manakova E; Gražulis S; Tumkevi?ius S; Matulis D

2010-11-01

80

New 2-aryl-1,4-naphthoquinone-1-oxime methyl ether compound induces microtubule depolymerization and subsequent apoptosis.  

Science.gov (United States)

In this study, we describe the antitumor activity of QO-1, one of the new 2-aryl-1,4-naphthoquinone-1-oxime methyl ether derivatives. QO-1 is a derivative of macarpine, a natural occurring product from Rutaceae plant. It could potently inhibit cell growth when tested on 19 cancer cell lines. To investigate its mechanism, two cell lines (HeLa and MCF-7) sensitive to QO-1 were selected. Based on flow cytometry, it was found to induce G(2)/M-phase arrest. Moreover, it could cause microtubule depolymerization both in vitro and in vivo. On the other hand, QO-1 activated spindle assembly checkpoint (SAC) proteins. Expression of Bub1, one of the SAC, was gradually increased, reaching a peak after 16 - 20 h, and then gradually decreased. Instead, QO-1 increased the sub-G(1) population, which suggested a cell death population. Actually, expression of Bcl-2 family proteins and activation of caspase-3/7 were evidences of apoptosis. Consistent with these results, cells with DNA fragmentation and multinucleated cells were increased time-dependently after QO-1 exposure. In conclusion, QO-1 has promising antitumor effects via microtubule depolymerization. PMID:22447301

Sato, Hiromi; Yamada, Ryota; Yanagihara, Midori; Okuzawa, Hiroko; Iwata, Hiroki; Kurosawa, Ayako; Ichinomiya, Saki; Suzuki, Rina; Okabe, Hiroyuki; Yano, Tomohiro; Kumamoto, Takuya; Suzuki, Noriyuki; Ishikawa, Tsutomu; Ueno, Koichi

2012-03-14

 
 
 
 
81

Exploring the effect of N-substitution in nor-lobelane on the interaction with VMAT2: discovery of a potential clinical candidate for treatment of methamphetamine abuse.  

UK PubMed Central (United Kingdom)

A series of N-substituted lobelane analogues was synthesized and evaluated for their [(3)H]dihydrotetrabenazine binding affinity at the vesicular monoamine transporter and for their inhibition of vesicular [(3)H]dopamine uptake. Compound 19a, which contains an N-1,2(R)-dihydroxypropyl group, had been identified as a potential clinical candidate for the treatment of methamphetamine abuse.

Zheng G; Horton DB; Penthala NR; Nickell JR; Culver JP; Deaciuc AG; Dwoskin LP; Crooks PA

2013-03-01

82

Synthesis and ?-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-?-d-glucopyranosides.  

UK PubMed Central (United Kingdom)

A series of N-substituted 1-aminomethyl-?-d-glucopyranoside derivatives was prepared. These novel synthetic compounds were assessed in vitro for inhibitory activity against yeast ?-glucosidase and both rat intestinal ?-glucosidases maltase and sucrase. Most of the compounds displayed ?-glucosidase inhibitory activity, with IC50 values covering the wide range from 2.3?M to 2.0mM. Compounds 19a (IC50=2.3?M) and 19b (IC50=5.6?M) were identified as the most potent inhibitors for yeast ?-glucosidase, while compounds 16 (IC50=7.7 and 15.6?M) and 19e (IC50=5.1 and 10.4?M) were the strongest inhibitors of rat intestinal maltase and sucrase. Analysis of the kinetics of enzyme inhibition indicated that 19e inhibited maltase and sucrase in a competitive manner. The results suggest that the aminomethyl-?-d-glucopyranoside moiety can mimic the substrates of ?-glucosidase in the enzyme catalytic site, leading to competitive enzyme inhibition. Moreover, the nature of the N-substituent has considerable influence on inhibitory potency.

Bian X; Fan X; Ke C; Luan Y; Zhao G; Zeng A

2013-09-01

83

New N-(substituted alkyl)-piperidine or piperazine derivatives, are cellular proliferation inhibitors useful e.g. for treating cancer or inflammatory or autoimmune diseases  

UK PubMed Central (United Kingdom)

Piperidine or piperazine derivatives (I), N-substituted by a 4-6C n-alkyl group terminally substituted by a group containing two (hetero)aryl moieties, are new. Piperidine or piperazine derivatives of formula (I) and their salts are new. Ar1aryl, heteroaryl or heterocyclyl (all optionally substituted (os) by 1-5 of halo, alkyl, OH, hydroxyalkyl, alkoxy, alkoxyalkyl, alkylthio, alkylsulfonyl, haloalkyl, haloalkoxy, aryl and mono- or dialkylamino) X : O, S, CO, SO, SO2, NR3>, CR3>R4>, CR3>(OR5>), C=NOR3> or C=CR3>R4> R3>, R5>H, alkyl, alkylcarbonyl, aryl or arylalkyl R4>alkyl, aryl, arylalkyl or CN Ar21,4-phenylene (os by 1-4 groups M) or pyridine-2,5-diyl (bonded to Y in the 2-position and os by 1-3 groups M) each M : halo, alkyl, OH, alkoxy, CN, haloalkyl, haloalkoxy, NH2, mono- or dialkylamino, aminoalkyl or mono- or dialkylaminoalkyl Y' : O or NR R : H, alkyl or alkylcarbonyl n : 4-6 either (a) D : N R1>-CR8>R9>-CO-NR6>R7> -CR11>R12>-COOR10> or aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, hetercyclylalkyl, hydroxyalkyl, mono- or dialkylaminoalkyl or mono- or dialkylaminoalkylcarbonyl (all os) and R2>electron pair or (b) D : C and (i) R1>H and R2>aryl, arylalkyl, heterocyclyl, mono- or dialkylamino, OH, hydroxyalkyl, alkoxycarbonyl or arylcarbonyl (all os) (ii) R1>OH, alkylcarbonyl, alkoxycarbonyl, arylcarbonyl or CN and R2>aryl, arylalkyl or heterocyclyl (all os) or (iii) R1> + R2>group completing an os carbocyclic or heterocyclic ring R6>, R7>H or alkyl, cycloalkyl, cycloalkylalkyl, aryl, hydroxyalkyl, dialkylamino, heterocyclyl, heterocyclyalkyl, arylalkyl, heteroaryl, heteroarylalkyl, mono- or dialkylaminoalkyl or haloalkyl (all os) or NR6>R7>os heterocyclyl R8> - R12>H or alkyl alkyl moieties have 1-6C and cycloalkyl moieties 3-7C. [Image] - ACTIVITY : Cytostatic Antipsoriatic Antirheumatic Antiarthritic Anti-HIV Nephrotropic Antiarteriosclerotic Immunosuppressive Antiinflammatory. In tests in mice injected with U937 leukemia cells, intraperitoneal administration of 2-(4-(5-(4-(4-chlorophenoxy)-phenox y)-pentyl)-piperazin-1-yl)-N-isopropyl-acetamide (Ia) at a dose of 10 mg/kg once per day decreased the average tumor volume (relative to that in untreated controls) by 17.44%, 20.85% and 32.83% after 1, 7 and 10 days respectively. - MECHANISM OF ACTION : Cellular proliferation inhibitor.

BALAVOINE FABRICE; BATCH ALEXANDRE; ROLLAND CATHERINE

84

Compounds  

UK PubMed Central (United Kingdom)

The present invention is directed to compounds of formula (I), (Ia),(Ic) and (Id), compositions, and uses thereof as an inhibitor of the p38 kinase, and wherein, inter alia R1 is C(Z)N(R10')(CR10R20)vRb, C(Z)O(CR10R20)vRb, N(R10')C(Z)(CR10R20)vRb N(R10')C(Z)N(R10')(CR10R20)vRb or N(R10')OC(Z)(CR10R20)vRb R3 is C1-10 alkyl, C3-7 cycloalkyl, C3-7 cycloalkyl C1-10 alkyl, aryl, arylC1-10 alkyl, heteroarylC1-10 alkyl, or a heterocyclylC1-10 alkyl moiety, and wherein each of these moieties may be optionally substituted X is R2, OR2', S(O)mR2', (CH2)n'N(R10')S(O)mR2', (CH2)n'N(R10')C(O)R2', (CH2)n'NR4R14, (CH2)n'N(R2 ')(R2''), or N(R10')-Rh-NH-C(-N-CN)NRqRq' and R2 is hydrogen, C1-10 alkyl, C3-7 cycloalkyl, C3-7 cycloalkylalkyl, aryl, arylC1-10 alkyl, heteroaryl, heteroarylC1-10 alkyl, heterocyclic, or a heterocyclylC1-10 alkyl moiety, and wherein each of these moieties, excluding hydrogen, may be optionally substituted or a pharmaceutically acceptable salt thereof.

CALLAHAN JAMES F; WAN ZEHONG; YAN HONGXING; LIN XICHEN

85

Bis-aryl methanone compound is a candidate of nitric oxide producing elicitor and induces resistance in Nicotiana benthamiana against Phytophthora infestans.  

UK PubMed Central (United Kingdom)

Nitric oxide (NO) is important in some physiological responses of plants and plays a crucial role in the regulation of both defense responses and inducing resistance to fungal pathogens. NUBS-4190, a new bis-aryl-methanone compound elicited NO production and defense responses in Nicotiana benthamiana against Phytophthora infestans. NUBS-4190 induced resistance in N. benthamiana to P. infestans, without association of reactive oxygen generation and hypersensitive cell death. Callose induction was reduced in NUBS-4190-treated N. benthamiana leaves after challenge inoculation of P. infestans indicating the penetration resistance. Involvement of pathogenesis-related 1a (NbPR1a) and nitric oxide associated 1 (NbNOA1) genes in the induced resistance to N. benthamiana against P. infestans was found to be associated with resistance. Increased susceptibility in NbPR1a- and NbNOA1-silenced plants correlated with the constitutive accumulation of PR1a transcripts and NO associated salicylic acid. Moreover, reduced NO generation in NOA1 silenced N. benthamiana plants treated with NUBS-4190 indicated that NbNOA1 is involved in NUBS-4190-mediated NO production and is required for defense responses.

Monjil MS; Shibata Y; Takemoto D; Kawakita K

2013-02-01

86

N-SUBSTITUTED PIPERIDINE DERIVATIVES AS SEROTONIN RECEPTOR AGENTS.  

UK PubMed Central (United Kingdom)

Disclosed herein are compounds of Formula I, or a pharmaceutically acceptable salt, amide, ester, or prodrug thereof. Also disclosed are methods of inhibiting an activity of a monoamine receptor comprising contacting the monoamine receptor or a system containing the monoamine receptor with an effective amount of one or more of the compounds of Formula I. Disclosed are also methods of inhibiting an activation of a monoamine receptor comprising contacting the monoamine receptor or a system containing the monoamine receptor with an effective amount of one or more of the compounds of Formula I. Furthermore, methods of treating psychotic disease using a compound of Formula I are disclosed.

PAWLAS JAN

87

N-substituted piperidine derivatives as serotonin receptor agents  

UK PubMed Central (United Kingdom)

Disclosed herein are compounds of Formula I, or a pharmaceutically acceptable salt, amide, ester, or prodrug thereof. Also disclosed are methods of inhibiting an activity of a monoamine receptor comprising contacting the monoamine receptor or a system containing the monoamine receptor with an effective amount of one or more of the compounds of Formula I. Disclosed are also methods of inhibiting an activation of a monoamine receptor comprising contacting the monoamine receptor or a system containing the monoamine receptor with an effective amount of one or more of the compounds of Formula I. Furthermore, methods of treating psychotic disease using a compound of Formula I are disclosed.

CARL-MAGNUS ANDERSSON; NATHALIE SCHLIENGER; ALMA FEJZIC; HANSEN EVA L; JAN PAWLAS

88

N-SUBSTITUTED PIPERIDINE DERIVATIVES AS SEROTONIN RECEPTOR AGENTS  

UK PubMed Central (United Kingdom)

Disclosed herein are compounds of Formula I, or a pharmaceutically acceptable salt, amide, ester, or prodrug thereof. Also disclosed are methods of inhibiting an activity of a monoamine receptor comprising contacting the monoamine receptor or a system containing the monoamine receptor with an effective amount of one or more of the compounds of Formula I. Disclosed are also methods of inhibiting an activation of a monoamine receptor comprising contacting the monoamine receptor or a system containing the monoamine receptor with an effective amount of one or more of the compounds of Formula I. Furthermore, methods of treating psychotic disease using a compound of Formula I are disclosed.

ANDERSSON Carl-Magnus; SCHLIENGER Nathalie; FEJZIC Alma; HANSEN Eva Louise; PAWLAS Jan

89

Crystal structures of Klebsiella pneumoniae pantothenate kinase in complex with N-substituted pantothenamides.  

UK PubMed Central (United Kingdom)

N-Substituted pantothenamides are derivatives of pantothenate, the precursor in the biosynthesis of the essential metabolic cofactor coenzyme A (CoA). These compounds are substrates of pantothenate kinase (PanK) in the first step of CoA biosynthesis and possess antimicrobial activity against various pathogenic bacteria. Here we solved the crystal structure of the Klebsiella pneumoniae PanK (KpPanK) in complex with N-pentylpantothenamide (N5-Pan) to understand the molecular basis of its antimicrobial activity. The structure reveals a polar pocket interacting with the pantothenate moiety of N5-Pan and an aromatic pocket loosely protecting the pentyl tail, suggesting that the introduction of an aromatic ring to a new pantothenamide may enhance the compound's affinity to KpPanK. To test this idea, we synthesized N-pyridin-3-ylmethylpantothenamide (Np-Pan) and solved its co-crystal structure with KpPanK. The structure reveals two alternat conformations of the aromatic ring of Np-Pan bound at the aromatic pocket, providing the basis for further improvement of pantothenamide binding to KpPanK.

Li B; Tempel W; Smil D; Bolshan Y; Schapira M; Park HW

2013-08-01

90

N-SUBSTITUTED PERFLUOROALKYLATED PYRROLIDINES AS SURFACE MODIFIERS  

UK PubMed Central (United Kingdom)

The invention describes a composition comprising comprising a) a natural, semi-synthetic or synthetic polymer which is susceptible to oxidative, ther-mal or light-induced degradation, and b) a compound of the formula (I) wherein RF, R, Q and q are as defined herein, and are prepared from diallylamine, a perfluoroalkyl iodide and an amino-reactive compound selected from the group of carboxylic acids, anhydrides, acid chlorides, oxiranes, haloalkanes, isocyanates and ureas. The compounds of the formula I are useful as reducers of surface energy for natural, semi-synthetic or synthetic polymers, for example, for increasing the oil and water repellency and stain release of natural, semi-synthetic or synthetic polymers.

GERSTER MICHELE; THORAND STEPHAN

91

Amino acid sequence of the ligand-binding domain of the aryl hydrocarbon receptor 1 predicts sensitivity of wild birds to effects of dioxin-like compounds.  

UK PubMed Central (United Kingdom)

The sensitivity of avian species to the toxic effects of dioxin-like compounds (DLCs) varies up to 1000-fold among species, and this variability has been associated with interspecies differences in aryl hydrocarbon receptor 1 ligand-binding domain (AHR1 LBD) sequence. We previously showed that LD(50) values, based on in ovo exposures to DLCs, were significantly correlated with in vitro EC(50) values obtained with a luciferase reporter gene (LRG) assay that measures AHR1-mediated induction of cytochrome P4501A in COS-7 cells transfected with avian AHR1 constructs. Those findings suggest that the AHR1 LBD sequence and the LRG assay can be used to predict avian species sensitivity to DLCs. In the present study, the AHR1 LBD sequences of 86 avian species were studied, and differences at amino acid sites 256, 257, 297, 324, 337, and 380 were identified. Site-directed mutagenesis, the LRG assay, and homology modeling highlighted the importance of each amino acid site in AHR1 sensitivity to 2,3,7,8-tetrachlorodibenzo-p-dioxin and other DLCs. The results of the study revealed that (1) only amino acids at sites 324 and 380 affect the sensitivity of AHR1 expression constructs of the 86 avian species to DLCs and (2) in vitro luciferase activity of AHR1 constructs containing only the LBD of the species of interest is significantly correlated (r (2) = 0.93, p < 0.0001) with in ovo toxicity data for those species. These results indicate promise for the use of AHR1 LBD amino acid sequences independently, or combined with the LRG assay, to predict avian species sensitivity to DLCs.

Farmahin R; Manning GE; Crump D; Wu D; Mundy LJ; Jones SP; Hahn ME; Karchner SI; Giesy JP; Bursian SJ; Zwiernik MJ; Fredricks TB; Kennedy SW

2013-01-01

92

USE OF N-SUBSTITUTED SULFOXIMINES FOR CONTROL OF INVERTEBRATE PESTS  

UK PubMed Central (United Kingdom)

Methods to control certain invertebrates including insects in agricultura l, urban, animal health, and industrial systems by directly or systemically applying to a locus where control is desired an effective amount of a compou nd of N- substituted sulfoximines.

THOMAS JAMES D; HILL ROBERT L; GIFFORD JAMES MICHAEL; DEMARK JOSEPH J; MEADE THOMAS; LOSO MICHAEL R; HUANG JIM X; NUGENT BENJAMIN M; ROGERS RICHARD B; ZHU YUANMING

93

Derivatization and template-guided ligation of oligodeoxyribonucleotides using cyanogen bromide and N-substituted morpholines.  

UK PubMed Central (United Kingdom)

Cyanogen bromide has been found to induce the template-guided condensation of oligonucleotides only in the presence of N-substituted morpholines. Based on 31P, 1H and 13C NMR spectroscopy data, the mechanism of the phosphomonoester group activation by cyanogen bromide in N-substituted morpholine buffers is suggested. It has also been shown that BrCN can be used for the synthesis of oligonucleotide derivatives in aqueous solution.

Shabarova ZA; Fedorova OA; Dolinnaya NG; Gottikh MB

1997-12-01

94

Derivatization and Template-Guided Ligation of Oligodeoxyribonucleotides Using Cyanogen Bromide and N-Substituted Morpholines  

Science.gov (United States)

Cyanogen bromide has been found to induce the template-guided condensation of oligonucleotides only in the presence of N-substituted morpholines. Based on ^31P, ^1H and ^13C NMR spectroscopy data, the mechanism of the phosphomonoester group activation by cyanogen bromide in N-substituted morpholine buffers is suggested. It has also been shown that BrCN can be used for the synthesis of oligonucleotide derivatives in aqueous solution.

Shabarova, Z. A.; Fedorova, O. A.; Dolinnaya, N. G.; Gottikh, M. B.

1997-12-01

95

Structural Requirements of N-Substituted Spiropiperidine Analogues as Agonists of Nociceptin/Orphanin FQ Receptor  

Directory of Open Access Journals (Sweden)

Full Text Available The nociceptin/orphanin FQ (NOP) receptor is involved in a wide range of biological functions, including pain, anxiety, depression and drug abuse. Especially, its agonists have great potential to be developed into anxiolytics. In this work, both the ligand- and receptor-based three-dimensional quantitative structure–activity relationship (3D-QSAR) studies were carried out using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) techniques on 103 N-substituted spiropiperidine analogues as NOP agonists. The resultant optimal ligand-based CoMSIA model exhibited Q2 of 0.501, R2ncv of 0.912 and its predictive ability was validated by using an independent test set of 26 compounds which gave R2pred value of 0.818. In addition, docking analysis and molecular dynamics simulation (MD) were also applied to elucidate the probable binding modes of these agonists. Interpretation of the 3D contour maps, in the context of the topology of the active site of NOP, provided insight into the NOP-agonist interactions. The information obtained from this work can be used to accurately predict the binding affinity of related agonists and also facilitate the future rational design of novel agonists with improved activity.

Pingping Bao; Xiaole Zhang; Hong Ren; Yan Li; Zulin Mu; Shuwei Zhang; Guohui Li; Ling Yang

2011-01-01

96

MICROWAVE ASSISTED SYNTHESIS AND EVALUATION OF SOME FLUORO, CHLORO 2-N (SUBSTITUTED SCHIFF’S BASES) AMINO BENZOTHIAZOLES DERIVATIVES FOR THEIR ANTIINFLAMMATORY ACTIVITY  

Directory of Open Access Journals (Sweden)

Full Text Available The present research work is aimed to synthesize a series of various substituted benzothiazole derivatives containing 7-chloro-6-fluoro-N (substituted hydrozones) - benzothiazole.Structures of compounds has been established by means of IR, 1H-NMR and elemental analysis. The compounds MIIIc, MIIIf and MIIIJ at dose 5 mg/kg and 10mg/kg body.wt were evaluated for anti-inflammatory activity using carragennan induced paw edema method. The selected compounds have shown significant anti-inflammatory activity as compared to the standard drug. Compound MIIIJ (10 mg/kg body weight) has shown more significant result when compared with standard drug.

Muttu C.T; Bhanushali M.D; Hipparagi S.M; Tikare V.P; Karigar Asif

2010-01-01

97

Synthesis and Crystal Structures of N-Substituted Pyrazolines  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Four pyrazole compounds, 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde (1), 5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (2), 1-[5-(4-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone (3) and 1-[3-(4-fluorophenyl)-5-phenyl-4,5-d...

Wan-Sin Loh; Ching Kheng Quah; Tze Shyang Chia; Hoong-Kun Fun; Majal Sapnakumari; Badiadka Narayana; Balladka Kunhanna Sarojini

98

Modern Arylation Methods  

CERN Multimedia

Today, arylation methods are belonging to the most important reaction types in organic synthesis. Lutz Ackermann, a young and ambitious professor has gathered a number of top international authors to present the first comprehensive book on the topic. Starting from a historical review, the book covers hot topics like Palladium-catalyzed arylation of N-H and alpha-C-H-acidic Bonds, Copper-catalyzed arylation of N-H and O-H Bonds, direct arylation reactions, carbanion aromatic synthesis, arylation reactions of alkenes, alkynes and much more. This compact source of high quality information is indi

Ackermann, Lutz

2009-01-01

99

Solvent free preparation of N-substituted maleanilic acid  

Directory of Open Access Journals (Sweden)

Full Text Available Six N-maleanilic acids namely N-(4-carboxy)maleanilic acid (CAMAA), N-(4-bromo)maleanilic acid (BMAA), N-(4-hydroxy)maleanilic acid (HMAA), N-(3-hydroxy)maleanilic acid (mHMAA), N-(4-chloro)maleanilic acid (CMAA) and N-(4-methyl)maleanilic acid (MMAA) were prepared by solvent free reaction between maleic anhydride and a 4-carboxy, 4-bromo, 4-hydroxy, 3-hydroxy, 4-chloro and 4-methyl aniline derivatives in good to excellent yield. FT-IR, 1H-NMR and 13C-NMR spectra revealed the confirmation of these compounds in good agreement.DOI: http://dx.doi.org/10.4314/bcse.v27i1.15

H. Saedi

2013-01-01

100

Synthesis, characterization and biological screening of N-substituted derivatives of 5-benzyl-1,3,4-oxadiazole-2yl-2"-sulfanyl acetamide.  

Science.gov (United States)

A series of new N-substituted derivatives of 5-benzyl-1, 3, 4-oxadiazole-2yl-2"-sulfanyl acetamide (6a-n) were synthesized in three phases. The first phase involved the sequentially converting phenyl acetic acid into ester, hydrazide and finally cyclized in the presence of CS2 to afford 5-benzyl-1, 3, 4-oxadiazole-2-thiol. In the second phase N-substituted-2-bromoacetamides were prepared by reacting substituted amines with bromoacetyl bromide in basic media. In the third phase, 5-benzyl-1,3,4-oxadiazole-2-thiol was stirred with N-substituted-2-bromoacetamides in the presence of N,N-dimethyl formamide (DMF) and sodium hydride (NaH) to get the target compounds. Spectral techniques were used to confirm the structures of synthesized compounds. Synthesized compounds were screened against butyrylcho linesterase (BChE), acetylcholinesterase (AChE), and lipoxygenase enzymes (LOX) and were found to be relatively more active against acetylcholinesterase. PMID:23625417

Siddiqui, Sabahat Zahra; Rehman, Azizur; Abbasi, Muhammad Athar; Abbas, Nadia; Khan, Khalid Mohammed; Ashraf, Muhammad; Ejaz, Syeda Abida

2013-05-01

 
 
 
 
101

Synthesis and crystal structures of N-substituted pyrazolines.  

Science.gov (United States)

Four pyrazole compounds, 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde (1), 5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (2), 1-[5-(4-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone (3) and 1-[3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]propan-1-one (4), have been prepared by condensing chalcones with hydrazine hydrate in the presence of aliphatic acids, namely formic acid, acetic acid and propionic acid. The structures were characterized by X-ray single crystal structure determination. The dihedral angles formed between the pyrazole and the fluoro-substituted rings are 4.64(7)° in 1, 5.3(4)° in 2 and 4.89(6)° in 3. In 4, the corresponding angles for molecules A and molecules B are 10.53(10)° and 9.78(10)°, respectively. PMID:23429377

Loh, Wan-Sin; Quah, Ching Kheng; Chia, Tze Shyang; Fun, Hoong-Kun; Sapnakumari, Majal; Narayana, Badiadka; Sarojini, Balladka Kunhanna

2013-02-20

102

Synthesis and Crystal Structures of N-Substituted Pyrazolines  

Directory of Open Access Journals (Sweden)

Full Text Available Four pyrazole compounds, 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde (1), 5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (2), 1-[5-(4-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone (3) and 1-[3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]propan-1-one (4), have been prepared by condensing chalcones with hydrazine hydrate in the presence of aliphatic acids, namely formic acid, acetic acid and propionic acid. The structures were characterized by X-ray single crystal structure determination. The dihedral angles formed between the pyrazole and the fluoro-substituted rings are 4.64(7)° in 1, 5.3(4)° in 2 and 4.89(6)° in 3. In 4, the corresponding angles for molecules A and molecules B are 10.53(10)° and 9.78(10)°, respectively.

Wan-Sin Loh; Ching Kheng Quah; Tze Shyang Chia; Hoong-Kun Fun; Majal Sapnakumari; Badiadka Narayana; Balladka Kunhanna Sarojini

2013-01-01

103

Synthesis and crystal structures of N-substituted pyrazolines.  

UK PubMed Central (United Kingdom)

Four pyrazole compounds, 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde (1), 5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde (2), 1-[5-(4-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone (3) and 1-[3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]propan-1-one (4), have been prepared by condensing chalcones with hydrazine hydrate in the presence of aliphatic acids, namely formic acid, acetic acid and propionic acid. The structures were characterized by X-ray single crystal structure determination. The dihedral angles formed between the pyrazole and the fluoro-substituted rings are 4.64(7)° in 1, 5.3(4)° in 2 and 4.89(6)° in 3. In 4, the corresponding angles for molecules A and molecules B are 10.53(10)° and 9.78(10)°, respectively.

Loh WS; Quah CK; Chia TS; Fun HK; Sapnakumari M; Narayana B; Sarojini BK

2013-01-01

104

Adamantane derivatives of thiazolyl-N-substituted amide, as possible non-steroidal anti-inflammatory agents.  

Science.gov (United States)

A series of adamantane derivatives of thiazolyl-N-substituted amides were synthesized in a three-step reaction and tested for anti-inflammatory activity as well as lipoxygenase and cycloxygenase inhibitory actions. Theoretical calculation of their lipophilicity, as ClogP was performed. The effect of the synthesized compounds on inflammation, using the carrageenin-induced mouse paw oedema model was studied and compared to indomethacin. In general, the studied compounds were found to be potent anti-inflammatory agents (29.6-81.5%). Anti-inflammatory activity was influenced by some structural characteristics of the synthesized compounds. The lipoxygenase inhibitory activity was tested by the conversion of sodium linoleate to 13-hydroperoxylinoleic acid. Low inhibitory activity was observed. Evaluation of COX-1 and COX-2 inhibitory activities of the compounds revealed a COX-1 inhibitory potential, comparable to that of naproxen for some of the compounds and a low to moderate COX-2 inhibitory potential. Comparison of the in vivo and in vitro results leads to the conclusion that most compounds of this series may be involved in other mechanisms of inflammation, too. PMID:18603333

Kouatly, Omar; Geronikaki, Athina; Kamoutsis, Charalambos; Hadjipavlou-Litina, Dimitra; Eleftheriou, Phaedra

2008-07-07

105

Stoichiometric C-H arylation of tricarbonyl(arene)chromium complexes bearing pyridine directing groups.  

UK PubMed Central (United Kingdom)

Differentially substituted Cr(CO)3-complexed aryl pyridines have been shown to readily undergo stoichiometric palladation and subsequent arylation using boronic acid nucleophiles. The positioning of the aryl substituents has been shown to be key in governing substrate reactivity, whereby sterically congested compounds prevent the geometry required for cyclometallation.

Fuchter MJ; Judge DK; Weimar M; White AJ

2013-04-01

106

Stoichiometric C-H arylation of tricarbonyl(arene)chromium complexes bearing pyridine directing groups.  

Science.gov (United States)

Differentially substituted Cr(CO)3-complexed aryl pyridines have been shown to readily undergo stoichiometric palladation and subsequent arylation using boronic acid nucleophiles. The positioning of the aryl substituents has been shown to be key in governing substrate reactivity, whereby sterically congested compounds prevent the geometry required for cyclometallation. PMID:23503842

Fuchter, Matthew J; Judge, Dilraj K; Weimar, Marko; White, Andrew J P

2013-04-28

107

Synthesis of N-substituted 6-trifluoromethyl-1,3-oxazinanes  

International Nuclear Information System (INIS)

This work reports the synthesis of two new series of N-substituted 6-trifluoromethyl-1,3-oxazinanes and N-substituted 6-trifluoromethyl-1,3-oxazinan-2-ones from the cyclization of 4-ylamino-1,1,1-trifluoro-butan-2-ols with formaldehyde and triphosgene, respectively. The 4-ylamino-1,1,1-trifluoro-butan-2-ols were obtained in good yields from the reduction of the parent 4-ylamino-1,1,1-trifluoro-but-3-en-2-ones with hydrogen and 10% Pd/C. (author)

2005-01-01

108

Synthesis of N-substituted 6-trifluoromethyl-1,3-oxazinanes  

Energy Technology Data Exchange (ETDEWEB)

The work reports the synthesis of two new series of N-substituted 6-trifluoromethyl-1,3-oxazinanes and N-substituted 6-trifluoromethyl-1,3-oxazinan-2-ones from the cyclization of 4-ylamino-1,1,1-trifluoro-butan-2-ols with formaldehyde and triphosgene, respectively. The 4-ylamino-1,1,1-trifluoro-butan-2-ols were obtained in good yields from the reduction of the parent 4-ylamino-1,1,1-trifluoro-but-3-en-2-ones with hydrogen and 10% Pd/C. (author)

Zanatta, Nilo; Squizani, Adriana M.C.; Fantinel, Leonardo; Nachtigall, Fabiane M.; Borchhardt, Deise M.; Bonacorso, Helio G.; Martins, Marcos A.P. [Santa Maria Univ., RS (Brazil). Dept. de Quimica. Nucleo de Qumica de Heterociclos (NUQUIMHE)]. E-mail: zanatta@base.ufsm.br

2005-11-15

109

SINGLE-COMPONENT COATING HAVING ALKOXYSILANE-TERMINATED N-SUBSTITUTED UREA RESINS  

UK PubMed Central (United Kingdom)

The coating described herein attempts to provide this solution by synthesizing alkoxysilane- terminated N-substituted urea resins, then formulating them into moisture-curable single- component (IK) topside coatings. These coatings will provide greater external stability (to UV and visible radiation), cleanability, flexibility, cure times and lower VOC content than the currently qualified silicone alkyd topside coatings that are found on Navy ships. The single- component coating can include at least an alkoxysilane-terminated N-substituted urea resin, a reactive diluent, a pigment, a filler, and a catalyst. The resin can include an amino-functional silane substituted at the N-position and a non-aromatic isocyanate.

IEZZI ERICK B

110

Superacid synthesis of halogen containing N-substituted-4-aminobenzene sulfonamides: new selective tumor-associated carbonic anhydrase inhibitors.  

UK PubMed Central (United Kingdom)

A series of new, halogen containing N-substituted 4-aminobenzenesulfonamides were synthesized by using superacid HF/SbF5 chemistry and investigated as inhibitors of several human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, that is, the cytosolic hCA I and II and, the tumor-associated transmembrane isoforms hCA IX and XII. Despite the substitution of the sulfonamide function, the presence of fluorine atom(s) in ? position of the sulfonamide function strongly favors hCA inhibition. A similar effect of the ?-fluorinated alkyl substitution on the amino function has been also observed. Among the tested compounds, several chlorinated derivatives have been identified as selective nanomolar, tumor-associated isoforms inhibitors. These non-primary sulfonamides probably bind in the coumarin-binding site, at the entrance of the cavity, and not to the metal ion as the primary sulfonamide inhibitors.

Compain G; Martin-Mingot A; Maresca A; Thibaudeau S; Supuran CT

2013-03-01

111

Synthesis of nanodispersible 6-aryl-2,4-diamino-1,3,5-triazine and its derivatives  

Energy Technology Data Exchange (ETDEWEB)

A series of novel branched derivatives of 6-aryl-2,4-diamino-1,3,5-triazine from corresponding aryl nitriles and dicyanodiamide was synthesized. These compounds show a nanodispersibility and good thermal stability.

Padalkar, Vikas S.; Patil, Vikas S.; Phatangare, Kiran R.; Gupta, Vinod D.; Umape, Prashant G. [Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai 400019 (India); Sekar, N., E-mail: n.sekar@ictmumbai.edu.in [Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai 400019 (India)

2010-06-15

112

Synthesis and antimicrobial profile of N-substituted imidazolium oximes and their monoquaternary salts against multidrug resistant bacteria.  

Science.gov (United States)

Two different series of N-substituted imidazolium oximes and their monoquaternary salts were synthesized and biologically tested with respect to their ability to inhibit growth a diverse panel of antibiotic susceptible Gram-positive and antibiotic resistant Gram-negative bacteria as well fungal strains. The newly synthesized compounds were analyzed by spectral studies to confirm their structure. The preliminary results showed that all compounds tested possess promising antimicrobial potential against both susceptible Gram-positive and antibiotic resistant Gram-negative isolates, exhibiting a wide range of MIC values from 0.14 to 100.0?g/mL. The structure-activity relationship demonstrates that the p-methylphenyl and p-fluorophenyl groups in monoquaternary salts 6 and 7 attached directly to the imidazolium ring could be essential for observed remarkable inhibitory profiles against clinically important pathogens Pseudomonas aeruginosa (MIC=0.14?g/mL) and Klebsiella pneumoniae (MIC=1.56?g/mL). Furthermore, the broth microdilution assay was then used to investigate the antiresistance efficacy of compound 7 against fourteen extended-spectrum ?-lactamase (ESBL)-producing strains in comparison to eight clinically relevant antibiotics. Compound 7 exhibited a remarkable antiresistance profiles ranging between 0.39 and 12.50?g/mL against all of ESBL-producing strains, which leads to the suggestion that may be interesting candidate for development of new antimicrobials to combat multidrug resistant Gram-negative bacteria. PMID:24126094

Odžak, Renata; Sko?ibuši?, Mirjana; Maravi?, Ana

2013-09-25

113

[Comparative studies of enzyme-inducing ability of phenobarbital, methylphenobarbital, glutethimide and their N-substituted morphoalkylic derivatives  

UK PubMed Central (United Kingdom)

The authors examined the capability of N-substituted morpholinoalkyl derivated of phenobarbiral methylphenobarbital and glutetimide to induce drug-dissimilated enzymes in liver microsomes as those newly syntesized compounds were compared with the initial substances, which were enzyme inductors. They examined the following indices: duration of hexobarbital narcosis after a six day treatment of male white rats with one of the substances liver weight, related to the percentage of the whole body weight, protein content in liver homogenates and in microsomal fraction of liver, the activity of N-demetilase in liver. There was a considerable shortening of the duration of hexobarbital sleep due to barbiturates, more manifested in animals, treated with methylphenobarbital. Glutetimide shortened the narcosis statisticaly insignificant. The respective morpholonoalkylic derivatives not only did not shortened the narcotic sleep, but even slightly prolonged. it. The liver weight of the rats, treated with barbiturates, was increased with 25--30% while that of the rats treated with morpholinoalkylic derivatives did not differ from the liver weight of the control animals. The protein content in liver homogenates did not show statistically significant differences in the single groups. The protein content of the microsomal liver fraciton was increased in the animals, treated with barbiturates and glutetimide, while in the rats, treated with morphoalkylic derivatives the protein content did not differ from that of the controls, but it was even reduced after treatment with a derivative of glutetimide. Phenobarbital and methylphenobarbital increased significantly the activity of pyrimidone N-demetilase, while their N-substituted morpholinc-alkyli derivatives inhibited it.

Staneva-Sto?cheva D; Popov P; Kitova E; Mileva M

1977-01-01

114

DNA cleavage by photolysis of aryl sulfoxides.  

UK PubMed Central (United Kingdom)

Aryl sulfoxides have been identified as a class of organic compounds capable of inducing DNA cleavage in the presence of UV light. Phenyl sulfoxide and methyl phenyl sulfoxide were both shown to cleave pBR322 DNA at concentrations of 180 and 360 microM, respectively. Radical trapping studies indicate carbon-centered radicals are the active cleavage species.

Mayo DJ; Turner DP; Zucconi BE; Predecki AH

2007-11-01

115

DNA cleavage by photolysis of aryl sulfoxides.  

Science.gov (United States)

Aryl sulfoxides have been identified as a class of organic compounds capable of inducing DNA cleavage in the presence of UV light. Phenyl sulfoxide and methyl phenyl sulfoxide were both shown to cleave pBR322 DNA at concentrations of 180 and 360 microM, respectively. Radical trapping studies indicate carbon-centered radicals are the active cleavage species. PMID:17904368

Mayo, Daniel J; Turner, David P; Zucconi, Beth E; Predecki, Allison H

2007-09-15

116

Arylation of aldehyde homoenolates with aryl bromides.  

UK PubMed Central (United Kingdom)

A mild palladium catalyzed coupling of reactive aldehyde homoenolates with aryl bromides is described. Aldehyde homoenolates are generated by ring opening of cyclopropanols via a C-C cleavage step. The coupling generates aldehyde products at room temperature in 59-93% yield.

Cheng K; Walsh PJ

2013-05-01

117

Comparative cytotoxicity of N-substituted N'-(4-imidazole-ethyl)thiourea in precision-cut rat liver slices  

International Nuclear Information System (INIS)

In order to more rationally design thiourea-containing drugs and drug candidates, specifically thiourea-containing histamine H3 receptor antagonists, it is necessary to develop structure-toxicity relationships (STRs). For this purpose, the cytotoxicity of a series of thiourea-containing compounds was tested in precision-cut rat liver slices. A concentration of 1000 ?M of N-p-bromophenyl, N'-(4-imidazole-ethyl)thiourea (8) or N-p-nitrophenyl, N'-(4-imidazole-ethyl)thiourea (9) was found to cause cytotoxicity, evidenced as LDH leakage, resulting in more than 95% LDH leakage after 6 h. N-p-Methoxyphenyl, N'-(4-imidazole-ethyl)thiourea (6) caused 40.6±19.7% LDH leakage after 6 h. Control levels of cell death (1% methanol as control vehicle) were below 20% in 6 h. After 6 h of exposure, N-p-chlorophenyl, N'-(4-imidazole-ethyl)thiourea (7), 8, and 9 were already found to cause significant cytotoxicity at a concentration of 100 ?M. At 200 ?M, 9 was found to cause significantly more cytotoxicity than 7 and 8. N-Naphthyl, N'-(4-imidazole-ethyl)thiourea (12) was found to cause significant cytotoxicity towards precision-cut rat liver slices after 6 h of exposure to a concentration of 500 ?M. All other N-substituted, N'-(4-imidazole-ethyl)thiourea tested in this study were not found to be cytotoxic towards precision-cut rat liver slices within the 6 h of exposure up to a concentration of 1000 ?M. Intracellular glutathione (GSH) content and mitochondrial MTT reduction activity were also examined after exposure of slices to N-substituted, N'-(4-imidazole-ethyl)thiourea. Both of these markers, however, were not found to provide additional information regarding the possible mechanisms of cytotoxicity, i.e. GSH depletion or reduced mitochondrial activity since these markers did not clearly precede LDH leakage. A correlation was found between cytotoxicity towards precision-cut rat liver slices and Vmax/Km values for the formation of sulfenic acids from N-substituted N'-(4-imidazole-ethyl)thiourea by hepatic rat flavin-containing monooxygenases (FMO). The compound with the highest Vmax/Km value for the formation of sulfenic acids, 9, was also the most cytotoxic. Compounds with a significantly lower Vmax/Km value, 7, 8, and 12, were less cytotoxic than 9. Compounds with a Vmax/Km value for the formation of sulfenic acids lower than 0.0788 ml/(min mg) were found not to be cytotoxic towards precision-cut rat liver slices for concentrations up to 1000 ?M at an exposure time of 6 h. It is concluded, from this study, that N-phenyl substituted N'-(4-imidazole-ethyl)thiourea-containing electron-withdrawing p-substituents are cytotoxic towards precision-cut rat liver slices. Cytotoxicity is increased with increasing electron-withdrawing capacity of the p-substituent. A correlation was found to exist between Vmax/Km value for the formation of sulfenic acids by rat liver FMO enzymes and cytotoxicity.

2004-04-15

118

Polypeptoid brushes by surface-initiated polymerization of N-substituted glycine N-carboxyanhydrides.  

UK PubMed Central (United Kingdom)

Polypeptoid brushes were synthesized by surface-initiated polymerization of N-substituted glycine N-carboxyanhydrides on self-assembled amine monolayers. Using the presented grafting-from approach, polypeptoid brush thicknesses of approximately 40 nm could be obtained as compared to previously reported brush thicknesses of 4 nm. Moreover, hydrophilic, hydrophobic and amphiphilic polymer brushes were realized which are expected to have valuable applications as nonfouling surfaces and as model or references systems for surface grafted polypeptides.

Schneider M; Fetsch C; Amin I; Jordan R; Luxenhofer R

2013-06-01

119

Neat reaction microwave technology for the synthesis of N-substituted-1,4-dihydropyridines  

Energy Technology Data Exchange (ETDEWEB)

Hantzsch synthesis of N-substituted-1,4-dihydropyridines (1,4-DHP) was carried out using an environmentally benign procedure. Neat reactants were subjected to microwave irradiation (MWI) to give the required products in excellent yield. Appreciable results were not obtained when conventional synthesis using neat reactants was carried out. The good yield and rate enhancement observed in the case of microwave irradiation is attributed to the uniform heating effect of microwaves. (author)

Kidwai, M.; Mohan, R. [Univ. of Delhi, Dept. of Chemistry, Delhi (India)]. E-mail: mkidwai@mantraonline.com

2004-03-01

120

Polypeptoid brushes by surface-initiated polymerization of N-substituted glycine N-carboxyanhydrides.  

Science.gov (United States)

Polypeptoid brushes were synthesized by surface-initiated polymerization of N-substituted glycine N-carboxyanhydrides on self-assembled amine monolayers. Using the presented grafting-from approach, polypeptoid brush thicknesses of approximately 40 nm could be obtained as compared to previously reported brush thicknesses of 4 nm. Moreover, hydrophilic, hydrophobic and amphiphilic polymer brushes were realized which are expected to have valuable applications as nonfouling surfaces and as model or references systems for surface grafted polypeptides. PMID:23663172

Schneider, Maximilian; Fetsch, Corinna; Amin, Ihsan; Jordan, Rainer; Luxenhofer, Robert

2013-05-24

 
 
 
 
121

Experimental and computational studies on the tautomerism of N-substituted 3-amino-5-oxo-4-phenyl-1H-pyrazolo-1-carboxamides with antibacterial activity  

Science.gov (United States)

The tautomerism of N-substituted 3-amino-5-oxo-4-phenyl-1H-pyrazolo-1-carboxamides with antibacterial activity is studied with X-ray crystallography, IR, 1H and 13C NMR (including NOESY spectra) and quantum chemical calculations. It is found that the form with the keto group at position 5 is the preferred one in the crystalline state and in DMSO, although some fraction with the corresponding hydroxy group also occurs in both states. This finding was related to the antibacterial activity of the studied compounds as the energetic stabilization of the keto group may determine their proper hydrogen bond interactions with the bacterial enzyme.

Kaczor, Agnieszka A.; Wróbel, Tomasz; Karczmarzyk, Zbigniew; Wysocki, Waldemar; Mendyk, Ewaryst; Poso, Antti; Matosiuk, Dariusz; Pitucha, Monika

2013-11-01

122

A diversity oriented, microwave assisted synthesis of N-substituted 2-hydro-4-amino-pyrido[2,3-d]pyrimidin-7(8H)-ones.  

UK PubMed Central (United Kingdom)

A protocol for the synthesis of N-substituted 2-hydro-4-amino-pyrido[2,3-d]pyrimidin-7(8H)-ones (11) is described. Thus, the formylation of a 2-aminopyridone 12 in 85% formic acid/Ac(2)O, proceeding via in situ cyclization to the intermediate formamide 13, affords the corresponding 2-hydro-4-oxo-pyridopyrimidine 14, which is converted to a 4-chloro-pyridopyrimidine 15 upon treatment with POCl(3). The subsequent transformation to the title compounds is carried by treatment with the corresponding amine in MeOH under microwave irradiation conditions.

Mont N; Teixidó J; Borrell JI

2009-02-01

123

Alkyl and aryl trifluoromethoxytetrafluorosulfuranes  

UK PubMed Central (United Kingdom)

Novel compositions containing SF4-O-CF3 bonded to an organic group are disclosed. Aryl trifluoromethoxytetrafluorosulfuranes (or Ar-SF4-O-CF3), have been synthesized via the reaction of an aryl disulfide or thiol with fluoroxytrifluoromethane (F3COF). The compositions are useful synthons, which may be derivatized to yield highly electrically polar molecules, particularly novel liquid crystal compositions having high dielectric anisotropies cycloalkyl trifluoromethoxytetrafluorosulfuranes have similar utility.

BAILEY WADE H III; PESARESI RENO JOSEPH JR; CASTEEL WILLIAM JACK JR; PEZ GUIDO PETER

124

Alkyl and aryl trifluoromethoxytetrafluorosulfuranes  

UK PubMed Central (United Kingdom)

Novel compositions containing SF4-O-CF3 bonded to an organic group are disclosed. Aryl trifluoromethoxytetrafluorosulfuranes (or Ar-SF4-O-CF3), have been synthesized via the reaction of an aryl disulfide or thiol with fluoroxytrifluoromethane (F3COF). The compositions are useful synthons, which may be derivatized to yield highly electrically polar molecules, particularly novel liquid crystal compositions having high dielectric anisotropies. Cycloalkyl trifluoromethoxytetrafluorosulfuranes have similar utility.

BAILEY WADE H. III; PESARESI RENO JOSEPH JR; CASTEEL WILLIAM JACK JR; PEZ GUIDO PETER

125

Synthesis and biological evaluation of N-substituted sophocarpinic Acid derivatives as coxsackievirus?b3 inhibitors.  

Science.gov (United States)

A series of novel N-substituted sophocarpinic acid derivatives was designed, synthesized, and evaluated for their anti-enteroviral activities against coxsackievirus type?B3 (CVB3) and coxsackievirus type?B6 (CVB6) in Vero cells. Structure-activity relationship analysis revealed that the introduction of a benzenesulfonyl moiety on the 12-nitrogen atom in (E)-?,?-sophocarpinic acid might significantly enhance anti-CVB3 activity. Among the derivatives, (E)-12-N-(m-cyanobenzenesulfonyl)-?,?-sophocarpinic acid (11?m), possessing a meta-cyanobenzenesulfonyl group, exhibited potent activity against CVB3 with a selectivity index (SI) of 107. Furthermore, compound 11?m also showed a good oral pharmacokinetic profile, with an AUC value of 7.29??M?h(-1) in rats, and good safety through the oral route in mice, with an LD50 value of >1000?mg?kg(-1) ; these values suggest a druggable characteristic. Therefore, compound 11?m was selected for further investigation as a promising CVB3 inhibitor. We consider (E)-?,?-N-(benzenesulfonyl)sophocarpinic acids to be a novel class of anti-CVB3 agents. PMID:23881611

Gao, Li-Mei; Tang, Sheng; Wang, Yan-Xiang; Gao, Rong-Mei; Zhang, Xin; Peng, Zong-Gen; Li, Jian-Rui; Jiang, Jian-Dong; Li, Yu-Huan; Song, Dan-Qing

2013-07-23

126

Synthesis and acetylcholinesterase (AChE) inhibitory activity of some N -substituted-5-chloro-2(3 H )- benzoxazolone derivatives  

Directory of Open Access Journals (Sweden)

Full Text Available Alzheimer’s disease is a progressive neurodegenerative disorder of the central nervous system. Acetylcholinesterase inhibition is one of the proposed mechanisms for treatment of Alzheimer’s disease. Currently, acetylcholinesterase inhibitors such as tacrine,donepezil, rivastigmine and galantamine are applied in different stages of Alzheimer’s disease teratment. In recent years, various heterocyclic systems have been used as a skeletonto discover new acetylcholinesterase inhibitors. On the other hand, it is known that the benzoxazolone heterocyclic structure exhibited a wide range of biological activities. In this study, a seriesN-substituted-5-chloro-2(3H)-benzoxazolone derivatives were synthesized and evaluated their acetylcholinesterase inhibitory activity. These compounds were synthesized by Mannich reaction of 5-chloro-2(3H)-benzoxazolone with the appropriated amines.The acetylcholinesterase inhibitory activity of the title compounds was determined by colorimetric Ellman’s method. The preliminary screening results indicated that 5-chloro-2-(3H)-benzoxazolone scaffold demonstrated different inhibition range againstacetylcholinesterase enzyme depending on the structural differences

Zeynep Soyer; Sulunay Parlar; Vildan Alptuzun

2013-01-01

127

N'-substituted-2'-O,3'-N-carbonimidoyl bridged macrolides: novel anti-inflammatory macrolides without antimicrobial activity.  

UK PubMed Central (United Kingdom)

Macrolide antibiotics, like erythromycin, clarithromycin, and azithromycin, possess anti-inflammatory properties. These properties are considered fundamental to the efficacy of these three macrolides in the treatment of chronic inflammatory diseases like diffuse panbronchiolitis and cystic fibrosis. However, long-term treatment with macrolide antibiotics presents a considerable risk for promotion of bacterial resistance. We have examined antibacterial and anti-inflammatory effects of a novel macrolide class: N'-substituted 2'-O,3'-N-carbonimidoyl bridged erythromycin-derived 14- and 15-membered macrolides. A small focused library was prepared, and compounds without antimicrobial activity, which inhibited IL-6 production, were selected. Data analysis led to a statistical model that could be used for the design of novel anti-inflammatory macrolides. The most promising compound from this library retained the anti-inflammatory activity observed with azithromycin in lipopolysaccharide-induced pulmonary neutrophilia in vivo. Importantly, this study strongly suggests that antimicrobial and anti-inflammatory activities of macrolides are independent and can be separated, which raises development plausibility of novel anti-inflammatory therapeutics.

Bosnar M; Kragol G; Koštrun S; Vujasinovi? I; Bošnjak B; Benceti? Mihaljevi? V; Maruši? Ištuk Z; Kapi? S; Hrva?i? B; Brajša K; Tav?ar B; Jeli? D; Glojnari? I; Verbanac D; Culi? O; Padovan J; Alihodži? S; Erakovi? Haber V; Spaventi R

2012-07-01

128

Diverse functions of cationic Mn(III) N-substituted pyridylporphyrins, recognized as SOD mimics.  

UK PubMed Central (United Kingdom)

Oxidative stress, a redox imbalance between the endogenous reactive species and antioxidant systems, is common to numerous pathological conditions such as cancer, central nervous system injuries, radiation injury, diabetes etc. Therefore, compounds able to reduce oxidative stress have been actively sought for over 3 decades. Superoxide is the major species involved in oxidative stress either in its own right or through its progeny, such as ONOO?, H?O?, •OH, CO?•?, and •NO?. Hence, the very first compounds developed in the late 1970-ies were the superoxide dismutase (SOD) mimics. Thus far the most potent mimics have been the cationic meso Mn(III) N-substituted pyridylporphyrins and N,N'-disubstituted imidazolylporphyrins (MnPs), some of them with k(cat)(O?·?) similar to the k(cat) of SOD enzymes. Most frequently studied are ortho isomers MnTE-2-PyP??, MnTnHex-2-PyP??, and MnTDE-2-ImP??. The ability to disproportionate O?·? parallels their ability to remove the other major oxidizing species, peroxynitrite, ONOO?. The same structural feature that gives rise to the high k(cat)(O?·?) and k(red)(ONOO?), allows MnPs to strongly impact the activation of the redox-sensitive transcription factors, HIF-1?, NF-?B, AP-1, and SP-1, and therefore modify the excessive inflammatory and immune responses. Coupling with cellular reductants and other redox-active endogenous proteins seems to be involved in the actions of Mn porphyrins. While hydrophilic analogues, such as MnTE-2-PyP?? and MnTDE-2-ImP?? are potent in numerous animal models of diseases, the lipophilic analogues, such as MnTnHex-2-PyP??, were developed to cross blood brain barrier and target central nervous system and critical cellular compartments, mitochondria. The modification of its structure, aimed to preserve the SOD-like potency and lipophilicity, and diminish the toxicity, has presently been pursued. The pulmonary radioprotection by MnTnHex-2-PyP?? was the first efficacy study performed successfully with non-human primates. The Phase I toxicity clinical trials were done on amyotrophic lateral sclerosis patients with N,N'-diethylimidazolium analogue, MnTDE-2-ImP?? (AEOL10150). Its aggressive development as a wide spectrum radioprotector by Aeolus Pharmaceuticals has been supported by USA Federal government. The latest generation of compounds, bearing oxygens in pyridyl substituents is presently under aggressive development for cancer and CNS injuries at Duke University and is supported by Duke Translational Research Institute, The Wallace H. Coulter Translational Partners Grant Program, Preston Robert Tisch Brain Tumor Center at Duke, and National Institute of Allergy and Infectious Diseases. Metal center of cationic MnPs easily accepts and donates electrons as exemplified in the catalysis of O?·? dismutation. Thus such compounds may be equally good anti- and pro-oxidants; in either case the beneficial therapeutic effects may be observed. Moreover, while the in vivo effects may appear antioxidative, the mechanism of action of MnPs that produced such effects may be pro-oxidative; the most obvious example being the inhibition of NF-?B. The experimental data therefore teach us that we need to distinguish between the mechanism/s of action/s of MnPs and the effects we observe. A number of factors impact the type of action of MnPs leading to favorable therapeutic effects: levels of reactive species and oxygen, levels of endogenous antioxidants (enzymes and low-molecular compounds), levels of MnPs, their site of accumulation, and the mutual encounters of all of those species. The complexity of in vivo redox systems and the complex redox chemistry of MnPs challenge and motivate us to further our understanding of the physiology of the normal and diseased cell with ultimate goal to successfully treat human diseases.

Batinic-Haberle I; Rajic Z; Tovmasyan A; Reboucas JS; Ye X; Leong KW; Dewhirst MW; Vujaskovic Z; Benov L; Spasojevic I

2011-09-01

129

Synthesis of aryl trimethylstannanes from aryl amines: a sandmeyer-type stannylation reaction.  

Science.gov (United States)

Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C?C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. PMID:24014092

Qiu, Di; Meng, He; Jin, Liang; Wang, Shuai; Tang, Shengbo; Wang, Xi; Mo, Fanyang; Zhang, Yan; Wang, Jianbo

2013-09-06

130

An Expeditious Synthesis of N-substituted Pyrroles via Microwave-Induced Iodine-Catalyzed Reactions under Solventless Conditions  

Directory of Open Access Journals (Sweden)

Full Text Available An expeditious synthesis of N-substituted pyrroles has been developed by reacting 2,5-dimethoxy tetrahydrofuran and several amines using a microwave-induced molecular iodine-catalyzed reaction under solventless conditions.

Debasish Bandyopadhyay; Sanghamitra Mukherjee; Bimal K. Banik

2010-01-01

131

Complexation, thermal and catalytic studies of N-substituted piperazine, morpholine and thiomorpholine with some metal ions.  

UK PubMed Central (United Kingdom)

Several Cu(II), Pt(II) and Ni(II) complexes of N-substituted, piperazine (NN donor), morpholine (NO donor) and thiomorpholine (NS donor) derivatives were synthesized and their thermal behavior and catalytic activity in epoxidation reaction of cis-diphenylethylene were studied using oxygen sources NaOCl. The coordination compounds of Cu(II), Pt(II) and Ni(II) having general formula [MLCl]Cl, [ML2l]Cl2 or [ML]Cl2 with tetra coordinated geometry around metal ions have been isolated as solid. All the ligands and complexes were identified by spectroscopic methods and elemental analysis, magnetic measurements, electrical conductance and thermal analysis. A square planer structures have been proposed for all complexes. The thermal stability of the complexes discussed in terms of ligands donor atoms, geometry and central metal ions. The complexes have a similar thermal behavior for the selected metal ions. The thermogravimetric analyses suggest high thermal stability for most complexes followed by thermal decomposition in different steps. The decomposition processes were observed as water elimination, chloride anion removal and degradation of the organic ligands. Catalytic ability of the complexes were examined and found that all the complexes can effectively catalyze the epoxidation of cis-stilbene with NaOCl.

Kacan M; Turkyilmaz M; Karabulut F; Altun O; Baran Y

2013-09-01

132

N-substituted phenoxazine and acridone derivatives: structure-activity relationships of potent P2X4 receptor antagonists.  

UK PubMed Central (United Kingdom)

P2X4 receptor antagonists have potential as drugs for the treatment of neuropathic pain and neurodegenerative diseases. In the present study the discovery of phenoxazine derivatives as potent P2X4 antagonists is described. N-Substituted phenoxazine and related acridone and benzoxazine derivatives were synthesized and optimized with regard to their potency to inhibit ATP-induced calcium influx in 1321N1 astrocytoma cells stably transfected with the human P2X4 receptor. In addition, species selectivity (rat, mouse, human) and receptor subtype selectivity (versus P2X1,2,3,7) were investigated. The most potent P2X4 antagonist of the present series was N-(benzyloxycarbonyl)phenoxazine (26, PSB-12054) with an IC(50) of 0.189 ?M and good selectivity versus the other human P2X receptor subtypes. N-(p-Methylphenylsulfonyl)phenoxazine (21, PSB-12062) was identified as a selective P2X4 antagonist that was equally potent in all three species (IC(50): 0.928-1.76 ?M). The compounds showed an allosteric mechanism of action. The present study represents the first structure-activity relationship analysis of P2X4 antagonists.

Hernandez-Olmos V; Abdelrahman A; El-Tayeb A; Freudendahl D; Weinhausen S; Müller CE

2012-11-01

133

N-substituted phenoxazine and acridone derivatives: structure-activity relationships of potent P2X4 receptor antagonists.  

Science.gov (United States)

P2X4 receptor antagonists have potential as drugs for the treatment of neuropathic pain and neurodegenerative diseases. In the present study the discovery of phenoxazine derivatives as potent P2X4 antagonists is described. N-Substituted phenoxazine and related acridone and benzoxazine derivatives were synthesized and optimized with regard to their potency to inhibit ATP-induced calcium influx in 1321N1 astrocytoma cells stably transfected with the human P2X4 receptor. In addition, species selectivity (rat, mouse, human) and receptor subtype selectivity (versus P2X1,2,3,7) were investigated. The most potent P2X4 antagonist of the present series was N-(benzyloxycarbonyl)phenoxazine (26, PSB-12054) with an IC(50) of 0.189 ?M and good selectivity versus the other human P2X receptor subtypes. N-(p-Methylphenylsulfonyl)phenoxazine (21, PSB-12062) was identified as a selective P2X4 antagonist that was equally potent in all three species (IC(50): 0.928-1.76 ?M). The compounds showed an allosteric mechanism of action. The present study represents the first structure-activity relationship analysis of P2X4 antagonists. PMID:23075067

Hernandez-Olmos, Victor; Abdelrahman, Aliaa; El-Tayeb, Ali; Freudendahl, Diana; Weinhausen, Stephanie; Müller, Christa E

2012-11-01

134

Synthesis of N-substituted 6-trifluoromethyl-1,3-oxazinanes  

Scientific Electronic Library Online (English)

Full Text Available Abstract in portuguese Este trabalho apresenta a síntese de duas novas séries de 6-trifluormetil-1,3-oxazinanas N-substituídas e 6-trifluormetil-1,3-oxazinan-2-onas N-substituídas, a partir da ciclização de 4-ilamino-1,1,1-trifluor-butan-2-óis com formaldeído e trifosgênio, respectivamente. Os 4-ilamino-1,1,1-trifluor-butan-2-óis foram obtidos através da reação de redução dos precursores 4-ilamino-1,1,1-trifluor-but-3-en-2-onas, utilizando hidrogênio e 10% Pd/C, com bons rendimentos. Abstract in english This work reports the synthesis of two new series of N-substituted 6-trifluoromethyl-1,3-oxazinanes and N-substituted 6-trifluoromethyl-1,3-oxazinan-2-ones from the cyclization of 4-ylamino-1,1,1-trifluoro-butan-2-ols with formaldehyde and triphosgene, respectively. The 4-ylamino-1,1,1-trifluoro-butan-2-ols were obtained in good yields from the reduction of the parent 4-ylamino-1,1,1-trifluoro-but-3-en-2-ones with hydrogen and 10% Pd/C.

Zanatta, Nilo; Squizani, Adriana M. C.; Fantinel, Leonardo; Nachtigall, Fabiane M.; Borchhardt, Deise M.; Bonacorso, Helio G.; Martins, Marcos A. P.

2005-12-01

135

Palladium-catalyzed direct ?-arylation of methyl sulfones with aryl bromides.  

UK PubMed Central (United Kingdom)

A direct and efficient approach for palladium-catalyzed arylation of aryl and alkyl methyl sulfones with aryl bromides has been developed. The catalytic system affords arylated sulfones in good to excellent yields (73-90%).

Zheng B; Jia T; Walsh PJ

2013-04-01

136

Antimalarial activity of 9a-N substituted 15-membered azalides with improved in vitro and in vivo activity over azithromycin.  

UK PubMed Central (United Kingdom)

Novel classes of antimalarial drugs are needed due to emerging drug resistance. Azithromycin, the first macrolide investigated for malaria treatment and prophylaxis, failed as a single agent and thus novel analogues were envisaged as the next generation with improved activity. We synthesized 42 new 9a-N substituted 15-membered azalides with amide and amine functionalities via simple and inexpensive chemical procedures using easily available building blocks. These compounds exhibited marked advances over azithromycin in vitro in terms of potency against Plasmodium falciparum (over 100-fold) and high selectivity for the parasite and were characterized by moderate oral bioavailability in vivo. Two amines and one amide derivative showed improved in vivo potency in comparison to azithromycin when tested in a mouse efficacy model. Results obtained for compound 6u, including improved in vitro potency, good pharmacokinetic parameters, and in vivo efficacy higher than azithromycin and comparable to chloroquine, warrant its further development for malaria treatment and prophylaxis.

Peri? M; Fajdeti? A; Rup?i? R; Alihodži? S; Ziher D; Bukvi? Kraja?i? M; Smith KS; Ivezi?-Schönfeld Z; Padovan J; Landek G; Jeli? D; Hutinec A; Mesi? M; Ager A; Ellis WY; Milhous WK; Ohrt C; Spaventi R

2012-02-01

137

Synthesis, growth and characterization of new 1,3,4 -thiadiazole-5-(n-substituted)-sulfonamides cristals  

Scientific Electronic Library Online (English)

Full Text Available Abstract in spanish Nuevas 1,3,4-tiadiazol-5-(N-substituidas)-sulfonamidas, inhibidores de anhidrasa carbónica, fueron obtenidas incorporando los grupos N-ciclohexil, N-benzil and N-[sec-butil], por una síntesis optimizada y monocristales de las mismas fueron crecidos desde alcohol absoluto por evaporación lenta a temperatura ambiente hasta dimensiones adecuadas para medidas de DRX. Los datos estructurales de estos compuestos monoclínicos son comparados con los de otras fases r (more) elacionadas. El grupo sulfonil presenta una geometría tetraédrica distorsionada alrededor del átomo de S. Los diferentes sustituyentes introducidos no producen modificaciones en la estructura del anillo 1,3,4-tiadiazol. El análisis térmico de las tres fases muestra descomposición total a temperaturas por encima del punto de fusión. Los espectros FTIR confirman la formación de los compuestos y es el primer aporte sobre el conocimiento de la unión puente hidrógeno NH...N en estas sulfonamidas. Abstract in english New 1,3,4-thiadiazole-5-(N-substituted)-sulfonamide derivatives incorporating N-cyclohexyl, N-benzyl and N-[sec-butyl] moieties, carbonic anhydrase inhibitors, have been obtained by an optimized synthesis. Single crystals of these sulfonamides have been successfully grown up to suitable dimensions for X-ray diffraction measurements by slow evaporation of solvent at room temperature. Structural data for these monoclinic compounds are compared with those of relate (more) d phases. The sulfonyl moiety presents a distorted tetrahedral arrangement around the S atom. The different groups introduced cause no observable modifications of the 1,3,4-thiadiazole ring structure. Thermal analysis show total sample degradation at temperatures higher than that of the melting point of the three phases. The FTIR spectra confirm the compounds formation and provide a first insight on the modes of NH…N hydrogen bond in these sulfonamides.

Camí, G.E.; Ramírez de Arellano, M.del C.; Fustero, S.; Pedregosa, J.C.

2006-12-01

138

Solid-Phase Synthesis of N-Substituted Glycine Oligomers (??Peptoids) and Derivatives  

Directory of Open Access Journals (Sweden)

Full Text Available Peptoids (N-substituted polyglycines and extended peptoids with variant backbone amino-acid monomer units) are oligomeric synthetic polymers that are becoming a valuable molecular tool in the biosciences. Of particular interest are their applications to the exploration of peptoid secondary structures and drug design. Major advantages of peptoids as research and pharmaceutical tools include the ease and economy of synthesis, highly variable backbone and side-chain chemistry possibilities. At the same time, peptoids have been demonstrated as highly active in biological systems while resistant to proteolytic decay. This review with 227 references considers the solid-phase synthetic aspects of peptoid preparation and utilization up to 2010 from the instigation, by R. N. Zuckermann et al., of peptoid chemistry in 1992.

Adrian S. Culf; Rodney J. Ouellette

2010-01-01

139

Synthesis and complexing properties of N-substituted mono- or diaza-crown ethers  

International Nuclear Information System (INIS)

[en] N-substituted mono- or diaza-crown ethers, containing fragments of ethylacetate, ethylene glycol ethers, n-methoxy and n-nitrobenzene group in their lateral chains, were synthesized. Their interaction with ions of alkali and alkaline-earth metals (MI=Li-Cs; MII=Ca, Sr, Ba) was studied by the method of pH-metric titration in methanol at 25 Deg C.; It is shown that introduction of substituent changes the complexing ability of basic macrocycle as a result of nitrogen atoms basicity change and participation of the lateral groups in additional coordination with the complexing ion[ru] ????????????? N-?????????? ????- ? ??????????-?????, ?????????? ? ??????? ????? ????????? ???????????, ?????? ????????????, n-??????? ? n-??????????????? ?????. ??????? pH-???????????? ?????????? ? ???????? ??? 25 ???? C ??????? ?? ?????????????? ? ?????? ???????? ? ???????????????? ???????? (MI=Li-Cs; MII=Ca, Sr, Ba). ????????, ??? ???????? ???????????? ???????? ??????????????????? ??????????? ???????? ?????????? ? ?????????? ????????? ?????????? ?????? ????? ? ??????? ??????? ????? ? ?????????????? ??????????? ? ????????????? ?????

2003-01-01

140

Electrochemical synthesis and characterization of N-substituted polypyrrole derivatives on nickel  

International Nuclear Information System (INIS)

1-Dodecylpyrrole (PyCH3) and 12-(pyrrol-1-yl)dodecane-1-thiol (PySH) films have been successfully electrochemically polymerised on a nickel electrode from acetonitrile solutions containing the monomer and the lithium perchlorate as supporting electrolyte. The electrochemical study of the polymer growth has been carried out by cyclic voltammetry (CV) detecting the nickel dissolution during electropolymerisation. Several surface spectroscopic and microscopic techniques have been used to characterize the surface in term of chemical composition and polymer topography. The presence of unbound and unoxidised thiol groups at the PPySH surface has been evidenced together with a very strong adhesion to the nickel substrate. Furthermore, N-substituted pyrrole derivatives exhibited some corrosion protection properties in neutral NaCl medium.

2007-03-20

 
 
 
 
141

Synthesis and characterization of methacrylamidopropyltrimethylammonium chloride and N-substituted acrylamide ionomers  

Directory of Open Access Journals (Sweden)

Full Text Available Quaternary ammonium ionomers of Methacrylamidopropyltrimethyl ammonium chloride with N-substituted acrylamides were prepared at 55±1°C using azobiscyanovaleric acid (ACVA) initiator. The monomers and ionomers were characterized by 1H- and 13C-NMR spectroscopy and the copolymer composition was calculated from elemental analysis data. The reduced viscosity of ionomers in methanol behaves as non-polyelectrolytes at lower mole percentage and as polyelectrolyte at higher mole percentage. The molecular weights of ionomers were found to be high and the polydispersity index values indicate termination mainly by disproportionation. The glass transition temperature (Tg) of ionomers were greater than those of the corresponding homopolymers, attributed to a reduction in segmental mobility. The initial decomposition temperature (IDT) showed that the stability of ionomers increases with increasing mole percentage of ionic content.

2007-01-01

142

Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted Indoles  

DEFF Research Database (Denmark)

Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme).

Jensen, Thomas; Pedersen, Henrik

2008-01-01

143

Green and selective synthesis of N-substituted amides using water soluble porphyrazinato copper(II) catalyst  

Energy Technology Data Exchange (ETDEWEB)

N, N',N{sup ,} N{sup '}-Tetramethyl tetra-2,3-pyridinoporphyrazinato copper(II) methyl sulfate ([Cu(2,3-tmtppa)](MeSO{sub 4}){sub 4}) efficiently catalyzed the direct conversion of nitriles to N-substituted amides. The one pot selective synthesis of the N-substituted amides from nitriles and primary amines was performed in refluxing H{sub 2}O. The catalyst was recovered and reused at least four times, maintaining its efficiency. (author)

Ghodsinia, Sara S.E.; Akhlaghinia, Batool; Eshghi, Hossein, E-mail: akhlaghinia@um.ac.ir [Ferdowsi University of Mashhad (Iran, Islamic Republic of). Faculty of Sciences. Department of Chemistry; Safaei, Elham [Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan (Iran, Islamic Republic of). Department of Chemistry

2013-06-15

144

Synthesis, structure-activity relationship and biological evaluation of novel N-substituted matrinic acid derivatives as host heat-stress cognate 70 (Hsc70) down-regulators.  

Science.gov (United States)

Oxymatrine (1) is a natural anti-hepatitis B virus (HBV) drug that down-regulates host heat-stress cognate 70 (Hsc70) expression through a mechanism different from that of nucleosides. Taking Hsc70 as a target against HBV, 26 novel N-substituted matrinic acid analogs were designed, synthesized and evaluated for their regulation of Hsc70 mRNA expression with 1 as the lead. The SAR analysis revealed that (i) the carboxyl group at the 11-position was required for activity; (ii) introducing of a substituent on the nitrogen atom at the 12-position of 3, especially substituted benzyl, might significantly improve the activity. Among these analogs, compound 9p possessing N-p-methoxylbenzyl afforded an increased anti-HBV effect in comparison with 1. We consider 9p a promising anti-HBV candidate. PMID:21757347

Du, Na-Na; Li, Xin; Wang, Yu-Ping; Liu, Fei; Liu, Yan-Xin; Li, Chun-Xin; Peng, Zong-Gen; Gao, Li-Mei; Jiang, Jian-Dong; Song, Dan-Qing

2011-06-23

145

Synthesis, structure-activity relationship and biological evaluation of novel N-substituted matrinic acid derivatives as host heat-stress cognate 70 (Hsc70) down-regulators.  

UK PubMed Central (United Kingdom)

Oxymatrine (1) is a natural anti-hepatitis B virus (HBV) drug that down-regulates host heat-stress cognate 70 (Hsc70) expression through a mechanism different from that of nucleosides. Taking Hsc70 as a target against HBV, 26 novel N-substituted matrinic acid analogs were designed, synthesized and evaluated for their regulation of Hsc70 mRNA expression with 1 as the lead. The SAR analysis revealed that (i) the carboxyl group at the 11-position was required for activity; (ii) introducing of a substituent on the nitrogen atom at the 12-position of 3, especially substituted benzyl, might significantly improve the activity. Among these analogs, compound 9p possessing N-p-methoxylbenzyl afforded an increased anti-HBV effect in comparison with 1. We consider 9p a promising anti-HBV candidate.

Du NN; Li X; Wang YP; Liu F; Liu YX; Li CX; Peng ZG; Gao LM; Jiang JD; Song DQ

2011-08-01

146

Double hetero-Michael addition of N-substituted hydroxylamines to quinone monoketals: synthesis of bridged isoxazolidines.  

Science.gov (United States)

A general synthesis of bridged isoxazolidines from a double hetero-Michael addition of N-substituted hydroxylamines to quinone monoketals has been developed. The different addition order of N-benzylhydroxylamine and N-Boc hydroxylamine is also discussed. Moreover, the various functionalities in the isoxazolidine products allow facile derivatization. PMID:23829680

Yin, Zhiwei; Zhang, Jinzhu; Wu, Jing; Liu, Che; Sioson, Kate; Devany, Matthew; Hu, Chunhua; Zheng, Shengping

2013-07-05

147

ON THE ANTIOXIDANT EFFECTIVENESS OF N,N´–SUBSTITUTED P-PHENYLENEDIAMINES  

Directory of Open Access Journals (Sweden)

Full Text Available The ground-state geometry of six N,N’-substituted p-phenylenediamines (PPDs): N-phenyl-N’-dimethyl-butyl-p-phenylenediamine (6PPD), N-phenyl-N’-isopropyl-p-phenylenediamine (IPPD), N-phenyl-N’-(?-methylbenzyl)-p-phenylenediamine (SPPD), N-(2-methoxybenzyl)-N’-phenyl-p-phenylenediamine (MBPPD), N-benzyl-N’-phenyl-p-phenylenediamine (MBPPDH), N-(1-methyl-1-phenylethyl)-N’-phenyl-p-phenylene-diamine (CPPD) molecules, their radical structures and the energy characterisation of these molecules and radicals were theoretically investigated using PM3 method. Our calculations reveal the most probable radical formation in the order SPPD > MBPPD > MBPPDH > 6PPD > IPPD > CPPD. The theoretical values have been compared with the values obtained by the analysis of structural units contributions based on the results of non-isothermal DSC measurements. The results show that the most likely process is homolytic cleavage of C–H bond at the carbon atom in the neighbourhood of the amino nitrogen atom and the sterical arrangement is related to the antioxidant effectiveness of the antioxidants under study. The suggested models can be used for the interpretation and prediction of experimental data what is important from the technological point of view.

Zuzana Cibulková; Erik Klein; Vladimír Lukeš

2004-01-01

148

N-substituted aminomethanephosphonic and aminomethane-P-methylphosphinic acids as inhibitors of ureases.  

UK PubMed Central (United Kingdom)

Small unextended molecules based on the diamidophosphate structure with a covalent carbon-to-phosphorus bond to improve hydrolytic stability were developed as a novel group of inhibitors to control microbial urea decomposition. Applying a structure-based inhibitor design approach using available crystal structures of bacterial urease, N-substituted derivatives of aminomethylphosphonic and P-methyl-aminomethylphosphinic acids were designed and synthesized. In inhibition studies using urease from Bacillus pasteurii and Canavalia ensiformis, the N,N-dimethyl derivatives of both lead structures were most effective with dissociation constants in the low micromolar range (Ki=13±0.8 and 0.62±0.09 ?M, respectively). Whole-cell studies on a ureolytic strain of Proteus mirabilis showed the high efficiency of N,N-dimethyl and N-methyl derivatives of aminomethane-P-methylphosphinic acids for urease inhibition in pathogenic bacteria. The high hydrolytic stability of selected inhibitors was confirmed over a period of 30 days using NMR technique.

Berlicki L; Bochno M; Grabowiecka A; Bia?as A; Kosikowska P; Kafarski P

2012-05-01

149

N-substituted aminomethanephosphonic and aminomethane-P-methylphosphinic acids as inhibitors of ureases.  

Science.gov (United States)

Small unextended molecules based on the diamidophosphate structure with a covalent carbon-to-phosphorus bond to improve hydrolytic stability were developed as a novel group of inhibitors to control microbial urea decomposition. Applying a structure-based inhibitor design approach using available crystal structures of bacterial urease, N-substituted derivatives of aminomethylphosphonic and P-methyl-aminomethylphosphinic acids were designed and synthesized. In inhibition studies using urease from Bacillus pasteurii and Canavalia ensiformis, the N,N-dimethyl derivatives of both lead structures were most effective with dissociation constants in the low micromolar range (Ki=13±0.8 and 0.62±0.09 ?M, respectively). Whole-cell studies on a ureolytic strain of Proteus mirabilis showed the high efficiency of N,N-dimethyl and N-methyl derivatives of aminomethane-P-methylphosphinic acids for urease inhibition in pathogenic bacteria. The high hydrolytic stability of selected inhibitors was confirmed over a period of 30 days using NMR technique. PMID:21559954

Berlicki, Lukasz; Bochno, Marta; Grabowiecka, Agnieszka; Bia?as, Arkadiusz; Kosikowska, Paulina; Kafarski, Pawe?

2011-05-11

150

An N-substituted polyurea coating with high affinity for heparin.  

UK PubMed Central (United Kingdom)

A new N-substituted polyurea with tertiary amino groups in the polycarbamidic chain (NPUTA) has been synthesized. The polymer is soluble in C1-C4 alcohols, has high adhesion to polar molds, and has high H2O uptake (130-150%). The material can be coated on many biomaterials (polyurethanes, charcoal hemosorbents, cellulosic hemodialysis membranes), and high amounts of heparin can be adsorbed onto treated surfaces. NPUTA cast from 0.5-3.5% ethanol solutions can absorb large amounts of heparin from anti-coagulant solution (40-60 micrograms/cm2) and heparinized plasma. Heparin release into phosphate buffered saline (PBS) solution or plasma is minimal. The influence of NPUTA solution concentration and pre-absorbed heparin on the protein adsorption, platelet adhesion, surface induced hemolysis, and complement activation of these films has been investigated. Radiolabeled protein assays, radiolabeled platelet assays, and other methods were used. It was shown that modified surfaces for the listed materials, with heparinization, demonstrate improved in vitro blood compatibility without any changes in functional properties. For example, treatment with NPUTA/heparin does not reduce sorption of middle molecules by activated charcoal hemosorbent, while markedly and significantly decreasing platelet adhesion and complement activation. NPUTA/heparin modified, glutaraldehyde treated bovine pericardium exhibited significantly reduced calcification in a rat subcutaneous implant model. Other ex vivo circulation experiments also confirm the blood compatibility of different NPUTA treated surfaces.

Nemets EA; Karelskaya E; Sevastianov VI; Anderson JM; Harasaki H; Kim SW

1993-07-01

151

An N-substituted polyurea coating with high affinity for heparin.  

Science.gov (United States)

A new N-substituted polyurea with tertiary amino groups in the polycarbamidic chain (NPUTA) has been synthesized. The polymer is soluble in C1-C4 alcohols, has high adhesion to polar molds, and has high H2O uptake (130-150%). The material can be coated on many biomaterials (polyurethanes, charcoal hemosorbents, cellulosic hemodialysis membranes), and high amounts of heparin can be adsorbed onto treated surfaces. NPUTA cast from 0.5-3.5% ethanol solutions can absorb large amounts of heparin from anti-coagulant solution (40-60 micrograms/cm2) and heparinized plasma. Heparin release into phosphate buffered saline (PBS) solution or plasma is minimal. The influence of NPUTA solution concentration and pre-absorbed heparin on the protein adsorption, platelet adhesion, surface induced hemolysis, and complement activation of these films has been investigated. Radiolabeled protein assays, radiolabeled platelet assays, and other methods were used. It was shown that modified surfaces for the listed materials, with heparinization, demonstrate improved in vitro blood compatibility without any changes in functional properties. For example, treatment with NPUTA/heparin does not reduce sorption of middle molecules by activated charcoal hemosorbent, while markedly and significantly decreasing platelet adhesion and complement activation. NPUTA/heparin modified, glutaraldehyde treated bovine pericardium exhibited significantly reduced calcification in a rat subcutaneous implant model. Other ex vivo circulation experiments also confirm the blood compatibility of different NPUTA treated surfaces. PMID:8268551

Nemets, E A; Karelskaya, E; Sevastianov, V I; Anderson, J M; Harasaki, H; Kim, S W

152

Enantiomeric separation of racemic 4-aryl-1,4-dihydropyridines and 4-aryl-1,2,3,4-tetrahydropyrimidines on a chiral tetraproline stationary phase.  

UK PubMed Central (United Kingdom)

The chromatographic chiral resolution of 4-aryl-1,4-dihydropyridines (1-32), 4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidines (33-38), and 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidines (39-41) was studied on a tetraproline-immobilized chiral column synthesized in our lab. This tetraproline chiral stationary phase can resolve most of these compounds. The 4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidines (33-38) and 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidines (39-41) were more efficiently resolved than the racemic 4-aryl-1,4-dihydropyridines on the tetraproline chiralstationary phase. Analytes with 5,5-dimethyl groups (39-41) were less efficiently resolved than analytes without 5,5-dimethyl substituents (1-16). The 4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidines (39-41) without a sulfur atom were much more efficiently resolved than 4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidines (33-38). No obvious electronic effects on the resolution of any of these analytes (1-41) were observed on the tetraproline chiral stationary phase. The tetraproline chiral stationary phase separated enantiomers mainly via hydrogen bonding interactions.

Dai Z; Pittman CU Jr; Li T

2013-04-01

153

Aryl-heteroaryl derivatives as novel wake-promoting agents.  

Science.gov (United States)

In search of a next generation molecule to the novel wake-promoting agent modafinil, a series of aryl-heteroayl-derived wakefulness enhancing agents (in rats) was developed. From this work, compound 16 was separated into its enantiomers to profile them individually. PMID:23110414

Lesur, Brigitte; Lin, Yin G; Marcy, Val R; Aimone, Lisa D; Gruner, John; Bacon, Edward R; Chatterjee, Sankar

2012-12-26

154

Aryl-heteroaryl derivatives as novel wake-promoting agents.  

UK PubMed Central (United Kingdom)

In search of a next generation molecule to the novel wake-promoting agent modafinil, a series of aryl-heteroayl-derived wakefulness enhancing agents (in rats) was developed. From this work, compound 16 was separated into its enantiomers to profile them individually.

Lesur B; Lin YG; Marcy VR; Aimone LD; Gruner J; Bacon ER; Chatterjee S

2013-03-01

155

Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2-furanmethyl ester.  

Science.gov (United States)

Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, (1)H NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus , but most compounds exhibited good fungicidal activities against Corynespora cassiicola , Thanatephorus cucumeris , Botrytis cinerea , and Fusarium oxysporum . In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides. PMID:20151651

Li, Ying; Li, Bao-Ju; Ling, Yun; Miao, Hong-Jian; Shi, Yan-Xia; Yang, Xin-Ling

2010-03-10

156

Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2-furanmethyl ester.  

UK PubMed Central (United Kingdom)

Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, (1)H NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus , but most compounds exhibited good fungicidal activities against Corynespora cassiicola , Thanatephorus cucumeris , Botrytis cinerea , and Fusarium oxysporum . In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides.

Li Y; Li BJ; Ling Y; Miao HJ; Shi YX; Yang XL

2010-03-01

157

A New Routine for the Synthesis of N-substituted-N-(sulfonyl) bromoacetamides with ZnCl2 as a Catalyst  

Directory of Open Access Journals (Sweden)

Full Text Available A series of N-acylated N-substituted sulfonamides was prepared for the first time in good yields and with excellent conversion by the reaction of N-substituted-N-(p-toluene) sulfonamides (1) with acetyl chloride and bromoacetyl bromide (2), respectively, in the presence of a catalytic amount of anhydrous ZnCl2.

Martin Trávnícek; Milan Potácek

1999-01-01

158

Aryl Bromides and Aryl Chlorides for the Direct Arylation of Benzylic Amines Mediated by Ruthenium(II).  

UK PubMed Central (United Kingdom)

The ruthenium(II)-catalyzed sp(3) C-H bond arylation of benzylic amines with aryl halides is reported. In the present method, aryl iodides and, more importantly, also the cheaper aryl bromides and aryl chlorides can be applied as aryl sources. Additionally, the method does not require elaborate manipulations in a glove box and can be carried out in simple screw cap vials. Potassium pivalate proved to be beneficial for the transformation with aryl bromides or iodides as aryl source, but was not required for aryl chlorides. In the latter case, the addition of PPh3 led to high conversion. 3-Methyl and 3-phenyl pyridine were established as directing groups, and the substituent in the 3-position represents a key structural feature for high conversion. The directing group can be cleaved after the transformation, which allows access to diarylmethylamines. Mechanistic studies were carried out and critically compared to mechanistic reports of related transformations.

Dastbaravardeh N; Schnürch M; Mihovilovic MD

2013-05-01

159

Nucleophilic Addition of Nitrogen to Aryl Cations: Mimicking Titan Chemistry  

Science.gov (United States)

The reactivity of aryl cations toward molecular nitrogen is studied systematically in an ion trap mass spectrometer at 102 Pascal of nitrogen, the pressure of the Titan main haze layer. Nucleophilic addition of dinitrogen occurs and the nature of aryl group has a significant influence on the reactivity, through inductive effects and by changing the ground state spin multiplicity. The products of nitrogen activation, aryldiazonium ions, react with typical nitriles, aromatic amines, and alkynes (compounds that are relevant as possible Titan atmosphere constituents) to form covalently bonded heterocyclic products. Theoretical calculations at the level [DFT(B3LYP)/6-311++G(d,p)] indicate that the N2 addition reaction is exothermic for the singlet aryl cations but endothermic for their triplet spin isomers. The -OH and -NH2 substituted aryl ions are calculated to have triplet ground states, which is consistent with their decreased nitrogen addition reactivity. The energy needed for the generation of the aryl cations from their protonated precursors (ca. 340 kJ/mol starting with protonated aniline) is far less than that required to directly activate the nitrogen triple bond (the lowest energy excited state of N2 lies ca. 600 kJ/mol above the ground state). The formation of aza-aromatics via arene ionization and subsequent reactions provide a conceivable route to the genesis of nitrogen-containing organic molecules in the interstellar medium and Titan haze layers.

Li, Anyin; Jjunju, Fred P. M.; Cooks, R. Graham

2013-08-01

160

Nucleophilic Addition of Nitrogen to Aryl Cations: Mimicking Titan Chemistry.  

UK PubMed Central (United Kingdom)

The reactivity of aryl cations toward molecular nitrogen is studied systematically in an ion trap mass spectrometer at 10(2) Pascal of nitrogen, the pressure of the Titan main haze layer. Nucleophilic addition of dinitrogen occurs and the nature of aryl group has a significant influence on the reactivity, through inductive effects and by changing the ground state spin multiplicity. The products of nitrogen activation, aryldiazonium ions, react with typical nitriles, aromatic amines, and alkynes (compounds that are relevant as possible Titan atmosphere constituents) to form covalently bonded heterocyclic products. Theoretical calculations at the level [DFT(B3LYP)/6-311++G(d,p)] indicate that the N2 addition reaction is exothermic for the singlet aryl cations but endothermic for their triplet spin isomers. The -OH and -NH2 substituted aryl ions are calculated to have triplet ground states, which is consistent with their decreased nitrogen addition reactivity. The energy needed for the generation of the aryl cations from their protonated precursors (ca. 340 kJ/mol starting with protonated aniline) is far less than that required to directly activate the nitrogen triple bond (the lowest energy excited state of N2 lies ca. 600 kJ/mol above the ground state). The formation of aza-aromatics via arene ionization and subsequent reactions provide a conceivable route to the genesis of nitrogen-containing organic molecules in the interstellar medium and Titan haze layers.

Li A; Jjunju FP; Cooks RG

2013-08-01

 
 
 
 
161

New 1-Aryl-3-Substituted Propanol Derivatives as Antimalarial Agents  

Directory of Open Access Journals (Sweden)

Full Text Available This paper describes the synthesis and in vitro antimalarial activity against a P. falciparum 3D7 strain of some new 1-aryl-3-substituted propanol derivatives. Twelve of the tested compounds showed an IC50 lower than 1 ?M. These compounds were also tested for cytotoxicity in murine J774 macrophages. The most active compounds were evaluated for in vivo activity against P. berghei in a 4-day suppressive test. Compound 12 inhibited more than 50% of parasite growth at a dose of 50 mg/kg/day. In addition, an FBIT test was performed to measure the ability to inhibit ferriprotoporphyrin biocrystallization. This data indicates that 1-aryl-3-substituted propanol derivatives hold promise as a new therapeutic option for the treatment of malaria.

Silvia Pérez-Silanes; Luis Berrade; Rory N. García–Sánchez; Adela Mendoza; Silvia Galiano; Berta Martín Pérez-Solórzano; Juan J. Nogal-Ruiz; Antonio R. Martínez-Fernández; Ignacio Aldana; Antonio Monge

2009-01-01

162

Iron-catalyzed trifluoromethylation with concomitant C-C bond formation via 1,2-migration of an aryl group.  

UK PubMed Central (United Kingdom)

Iron-catalyzed trifluoromethylation with concomitant 1,2-migration of an aryl group starting from diaryl allyl alcohol was achieved under mild conditions. This reaction system affords ?-substituted-?-trifluoromethyl carbonyl compounds in high efficiency. In the case of substrates bearing different aryl groups, selective migration was observed.

Egami H; Shimizu R; Usui Y; Sodeoka M

2013-08-01

163

Iron-catalyzed trifluoromethylation with concomitant C-C bond formation via 1,2-migration of an aryl group.  

Science.gov (United States)

Iron-catalyzed trifluoromethylation with concomitant 1,2-migration of an aryl group starting from diaryl allyl alcohol was achieved under mild conditions. This reaction system affords ?-substituted-?-trifluoromethyl carbonyl compounds in high efficiency. In the case of substrates bearing different aryl groups, selective migration was observed. PMID:23846427

Egami, Hiromichi; Shimizu, Ryo; Usui, Yoshihiko; Sodeoka, Mikiko

2013-07-23

164

Synthesis, anticonvulsant, antioxidant and binding interaction of novel N-substituted methylquinazoline-2,4(1H,3H)-dione derivatives to bovine serum albumin: a structure-activity relationship study.  

Science.gov (United States)

A novel class of N-substituted glycosmicine derivatives was synthesized, and their anticonvulsant, antioxidant activity and interaction with bovine serum albumin (BSA) were evaluated. The synthesized compounds 4a-j were examined for anticonvulsant activity by maximal electroshock induced seizures (MESs) test and their neurotoxic effects were determined by rotorod test in mice. The structure-activity relationships (SARs) of these compounds were also investigated. Compounds 4d, 4g, 4i and 4j were found to have good protective effect from seizure. The in vitro antioxidant activity was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide radical scavenging assay. The interaction between novel N-substituted methylquinazoline-2,4(1H,3H)-dione (NMQ) and BSA was analyzed by fluorescence and ultraviolet spectroscopy at 304K under simulative physiological conditions. BSA fluorescence quenched by NMQ is discussed according to the Stern-Volmer equation. The binding constant and binding sites of NMQ with BSA were calculated. According to Forster non-radiation energy transfer theory, the binding distance (r) between NMQ and BSA was calculated. PMID:23583850

Prashanth, M K; Madaiah, M; Revanasiddappa, H D; Veeresh, B

2013-03-25

165

Synthesis, anticonvulsant, antioxidant and binding interaction of novel N-substituted methylquinazoline-2,4(1H,3H)-dione derivatives to bovine serum albumin: a structure-activity relationship study.  

UK PubMed Central (United Kingdom)

A novel class of N-substituted glycosmicine derivatives was synthesized, and their anticonvulsant, antioxidant activity and interaction with bovine serum albumin (BSA) were evaluated. The synthesized compounds 4a-j were examined for anticonvulsant activity by maximal electroshock induced seizures (MESs) test and their neurotoxic effects were determined by rotorod test in mice. The structure-activity relationships (SARs) of these compounds were also investigated. Compounds 4d, 4g, 4i and 4j were found to have good protective effect from seizure. The in vitro antioxidant activity was evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and superoxide radical scavenging assay. The interaction between novel N-substituted methylquinazoline-2,4(1H,3H)-dione (NMQ) and BSA was analyzed by fluorescence and ultraviolet spectroscopy at 304K under simulative physiological conditions. BSA fluorescence quenched by NMQ is discussed according to the Stern-Volmer equation. The binding constant and binding sites of NMQ with BSA were calculated. According to Forster non-radiation energy transfer theory, the binding distance (r) between NMQ and BSA was calculated.

Prashanth MK; Madaiah M; Revanasiddappa HD; Veeresh B

2013-06-01

166

C-aryl glucoside inhibitors of sodium dependent glucose transporters found in the intestine and kidney (SGLT2)  

UK PubMed Central (United Kingdom)

An C-aryl glucoside inhibitors of sodium dependent glucose transporters which is found in the intestine and kidney (SGLT2) is disclosed, wherein the C-aryl glucoside compound is represented by formula (I). These compounds are used in the manufacture of a medicament for treating diabetes and related diseases employing an SGLT2 inhibiting amount of the compound alone or in combination with another antidiabetic agent or other therapeutic agent.

ELLSWORTH BRUCE; WASHBURN WILLIAM N; SHER PHILIP M; WU GANG; MENG WEI

167

Toxicity Studies on Novel N-Substituted Bicyclo-Heptan-2-Amines at NMDA Receptors  

Directory of Open Access Journals (Sweden)

Full Text Available Several novel norcamphor derivatives were designed and synthesized as uncompetitive NMDA receptor antagonists at the phencyclidine (PCP) binding site. Such compounds have potential as ligands for understanding and possibly the treatment of several neurodegenerative disorders and other glutamate-dependent disorders. We examined the toxic effects of the compounds as compared with memantine, an NMDA receptor antagonist that is FDA approved for treatment of Alzheimer’s disease, by testing these compounds on two cell lines: MDCK (to mimic blood brain barrier) and N2a (a neuronal cell line). The compounds showed toxicity profiles similar to those of memantine i.e., dose dependence above 100 ?M and IC50 values above 150 ?M for each cell line. It is known that the serum level of memantine under therapeutic conditions in patients is about 1 µM, indicting these compounds could have acceptable therapeutic indexes. 2-Phenyl-N-(2-(piperidin-1-yl) ethyl)bicyclo[2.2.1]heptan-2-amine (5a) was found to possess acceptable toxicity profiles in both cell lines. Interestingly, this was the compound identified as a good lead in our previous studies based on binding and anticonvulsant (MES) activity studies. It has thus emerged as an excellent lead compound for further studies.

Natalia Coleman; Zeynep Ates-Alagoz; Boyenoh Gaye; Michelle Farbaniec; Shengguo Sun; Adeboye Adejare

2013-01-01

168

Synthesis of Aryl-Substituted Naphthalenoids as Potent Topoisomerase Inhibitors.  

UK PubMed Central (United Kingdom)

Twelve new aryl-substituted naphthalenoids (1-7, 9, 10, and 13-16) together with four known ones (8, and 11-13) have been designed and synthesized. Their antitumor activities were evaluated by sulforhodamine B assay on human breast cancer MDA-MB-231, human lung cancer A549 and human cervical cancer HeLa cell lines. Four compounds (2, 4, 10 and 12) showed potent inhibitory activities against the growth of the three cell lines with IC50 between 0.34-3.49 ?M, and were more potent than the reference etoposide (IC50 3.67-13.78 ?M). DNA relaxation assay revealed that compound 2 showed potent inhibitory activity against Topo II? in vitro. The structure-activity relationships of these compounds were discussed, suggesting that further structural optimizations of aryl-substituted naphthalenoids could lead to the discovery of potent antitumor agents targeting topoisomerases.

Shen Y; Chen W; Li Z; Shen Y

2013-09-01

169

Palladium-catalyzed coupling of aryl halides with alkynes  

UK PubMed Central (United Kingdom)

A method is provided to couple an aryl halide to an alkyne comprising reacting a compound of the formula ArX, wherein Ar is a substituted or unsubstituted aryl group and X is I or Br, with a compound of the formula HC[identical to]C-R1 wherein R1 is a substituted or unsubstituted organic group, in the presence of an effective amount of a phosphine-free, oxime-free palladium catalyst (C1-C4)alkyl N+(-OAc) or an alkali metal carbonate, to yield a compound of the formula Ar-C[identical to]C-R1, wherein the reaction is carried out in the absence of an organic amine or copper(I).

URGAONKAR SAMEER; VERKADE JOHN G

170

Toxicity Studies on Novel N-Substituted Bicyclo-Heptan-2-Amines at NMDA Receptors  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Several novel norcamphor derivatives were designed and synthesized as uncompetitive NMDA receptor antagonists at the phencyclidine (PCP) binding site. Such compounds have potential as ligands for understanding and possibly the treatment of several neurodegenerative disorders and other glutamate-depe...

Natalia Coleman; Zeynep Ates-Alagoz; Boyenoh Gaye; Michelle Farbaniec; Shengguo Sun; Adeboye Adejare

171

Palladium-catalyzed multicomponent synthesis of 2-aryl-2-imidazolines from aryl halides and diamines.  

UK PubMed Central (United Kingdom)

An efficient palladium-catalyzed three-component reaction that combines aryl halides, isocyanides, and diamines provides access to 2-aryl-2-imidazolines in yields up to 96%. Through variation of the diamine component, the reaction can be extended to the synthesis of 2-aryl-1H-benzimidazoles and 2-aryl-1,4,5,6-tetrahydropyrimidines.

Geden JV; Pancholi AK; Shipman M

2013-04-01

172

Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles  

Directory of Open Access Journals (Sweden)

Full Text Available A few 4-allyl/amino-5-aryl-1,2,4-triazoles were synthesized and tested for antibacterial and antifungal effects against Escherichia coli, Bacillus subtilis, Salmonella enteritidis, Staphylococcus aureus, Aspergillus niger and Candida albicans. 4-Allyl-5-aryl-1,2,4-triazoles were obtained by the oxidative cyclization of the appropriate 1-substituted-4-allylthiosemicarbazides and 4-amino-5-aryl-1,2,4-triazoles were obtained by cyclization of the potassium salts of appropriately substituted dithiocarbazinic acids with hydrazine hydrate. The new synthesized compounds were characterized using IR, 1H- NMR, 13C-NMR and UV spectral data together with elemental analysis.

Katica Colanceska-Ragenovic; Vesna Dimova; Vlado Kakurinov; Dora Gabor Molnar; Aleksandra Buzarovska

2001-01-01

173

Palladium-catalyzed amination of aryl nonaflates.  

Science.gov (United States)

The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands 2-4 and 6 allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos 5, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions. PMID:14656080

Anderson, Kevin W; Mendez-Perez, Maria; Priego, Julian; Buchwald, Stephen L

2003-12-12

174

Palladium-catalyzed amination of aryl nonaflates.  

UK PubMed Central (United Kingdom)

The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands 2-4 and 6 allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos 5, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions.

Anderson KW; Mendez-Perez M; Priego J; Buchwald SL

2003-12-01

175

Newer N-substituted anthranilic acid derivatives as potent anti-inflammatory agents.  

UK PubMed Central (United Kingdom)

The new 5-bromo-N-[2'-amino(1"-acetyl-5"substitutedaryl-2"-pyrazolin-3"-yl)-1',3',4'-oxadiazol-5'-ylmethyl]anthranilic acids 7a-7e and N-[2'-amino-(1"-acetyl-5"-substiutedaryl-2"-pyrazolin-3"-yl)-1',3',4'-thiadiazol-5'-ylmethyl]anthranilic acids 6'a-6'c have been synthesised from 5-bromo-N-(2'-aminosubstituedbenzylideneacetyl-1',3',4'-oxadiazol-5'-ylmethyl)anthranilic acids 6a-6e and N-(2'-aminosubstitutedbenzylideneacetyl-1',3',4'-thiadiazol-5'-ylmethyl)anthranilic acids 5'a-5'e, respectively. All these compounds have been screened in vivo for their anti-inflammatory and acute toxicity. Compounds 7b and 6'b were found to be potent member of this series, which showed 50.66 and 47.56%, respectively, inflammation inhibitory activity at a dose of 50 mg kg(-1) p.o., while standard drug, phenylbutazone, exhibited 45.52% anti-inflammatory activity at the same dose. However, 5-bromo-N-[2'-amino-[1"-acety1-5"-(para-methoxyphenyl)-2"-pyrazolin-3"-yl]-1',3',4'-oxidiazol-5'-ylmethyl]anthranilic acid (7b) was found to be the most active and less ulcerogcnic compound than the standard drag mid rest of the compounds of this series. The structures of these compounds have been established by IR, 1H-NMR spectroscopic data and elemental analyses.

Sharma S; Srivastava VK; Kumar A

2002-08-01

176

Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides.  

UK PubMed Central (United Kingdom)

The palladium-catalyzed ?-arylation of unactivated sulfoxides has been developed. The weakly acidic ?-protons of sulfoxides are reversibly deprotonated by LiOtBu, and a palladium phosphine complex facilitates the arylation. A variety of aryl methyl sulfoxides were coupled with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including dimethyl sulfoxide) and aryl chlorides proved to be suitable under the optimized conditions. This method was utilized to synthesize bioactive benzyl sulfoxide intermediates.

Jia T; Bellomo A; Baina KE; Dreher SD; Walsh PJ

2013-03-01

177

Intramolecular arylation of amino acid enolates.  

UK PubMed Central (United Kingdom)

Dianionic enolates formed from N'-aryl urea derivatives of amino acids undergo intramolecular C-arylation by attack of the enolate anion on the N'-aryl ring, leading to a hydantoin derivative of a quaternary amino acid. In situ IR studies allow identification of four intermediates on the reaction pathway.

Atkinson RC; Leonard DJ; Maury J; Castagnolo D; Volz N; Clayden J

2013-09-01

178

Intramolecular arylation of amino acid enolates.  

Science.gov (United States)

Dianionic enolates formed from N'-aryl urea derivatives of amino acids undergo intramolecular C-arylation by attack of the enolate anion on the N'-aryl ring, leading to a hydantoin derivative of a quaternary amino acid. In situ IR studies allow identification of four intermediates on the reaction pathway. PMID:24022183

Atkinson, Rachel C; Leonard, Daniel J; Maury, Julien; Castagnolo, Daniele; Volz, Nicole; Clayden, Jonathan

2013-09-26

179

Stability of sup(99m)Tc-labeled N-substituted iminodiacetic acids: ligand exchange reaction between sup(99m)Tc-HIDA and EDTA  

International Nuclear Information System (INIS)

Sup(99m)Tc-labeled N-(2,6-dimethylphenylcarbamoylmethyl) iminodiacetic acid (sup(99m)Tc-HIDA) underwent an acid catalyzed ligand exchange reaction in the presence of EDTA with half-lives of 2.5, 11, and 72 hr at pH values of 2.9, 4.4, and 6.4, respectively. The half-life for dissociation of sup(99m)Tc-HIDA in the presence of EDTA at pH 4.4 was found to be substantially independent of EDTA concentration. In addition, the formation constant for sup(99m)Tc-EDTA prepared by stannous ion reduction is 300 times larger than the overall formation constant for sup(99m)Tc-HIDA. This work indicates that sup(99m)Tc-(HIDA)2 exists as an anionic bis compound and that the bond between reduced technetium and N-substituted iminodiacetic acids should remain intact for long periods of time at physiologic pH and temperature. (author)

1977-01-01

180

Optimized Anti-pathogenic Agents Based on Core/Shell Nanostructures and 2-((4-Ethylphenoxy)ethyl)-N-(substituted-phenylcarbamothioyl)-benzamides  

Directory of Open Access Journals (Sweden)

Full Text Available The purpose of this study was to design a new nanosystem for catheter surface functionalization with an improved resistance to Staphylococcus aureus ATCC 25923 and Pseudomonas aeruginosa ATCC 27853 colonization and subsequent biofilm development. New 2-((4 ethylphenoxy)methyl)-N-(substituted-phenylcarbamothioyl)-benzamides were synthesized and used for coating a core/shell nanostructure. Their chemical structures were elucidated by NMR, IR and elemental analysis, being in agreement with the proposed ones. Fe3O4/C12 of up to 5 nm size had been synthesized with lauric acid as a coating agent and characterized by XRD, FT-IR, TGA, TEM and biological assays. The catheter pieces were coated with the fabricated nanofluid in magnetic field. The microbial adherence ability was investigated in 6 multiwell plates by using culture based methods and Scanning Electron Microscopy (SEM). The nanoparticles coated with the obtained compounds 1a–c inhibited the adherence and biofilm development ability of the S. aureus and P. aeruginosa tested strains on the catheter functionalized surface, as shown by the reduction of viable cell counts and SEM examination of the biofilm architecture. Using the novel core/shell/adsorption-shell to inhibit the microbial adherence could be of a great interest for the biomedical field, opening new directions for the design of film-coated surfaces with improved anti-biofilm properties.

Carmen Limban; Alexandru Mihai Grumezescu; Crina Saviuc; Georgeta Voicu; Gentiana Predan; Robert Sakizlian; Mariana Carmen Chifiriuc

2012-01-01

 
 
 
 
181

Synthesis and antimicrobial properties of N-substituted halides of (E)-azastilbenols.  

UK PubMed Central (United Kingdom)

The synthesis of 15 new N-benzyl substituted derivatives of (E)-gamma-azastilbenols-2'(3' and 4') and their antimicrobial activity are reported. In particular, compounds 1a-c, 1h and 2a-b showed good antibacterial activity against Staphlococcus aureus.

Prukala W; Wyrzykiewicz E; Kedzia B

1995-11-01

182

Green and selective synthesis of N-substituted amides using water soluble porphyrazinato copper(II) catalyst  

Scientific Electronic Library Online (English)

Full Text Available Abstract in portuguese N,N',N'',N'''-Tetrametil tetra(2,3-piridil)porfirazinato metil sulfato de cobre(II) ([Cu(2,3-tmtppa)](MeSO4)4) catalisou com sucesso a conversão direta de nitrilas a amidas N-substituídas. A síntese seletiva do tipo one pot de amidas N-substituídas a partir de nitrilas e aminas primárias foi realizada em refluxo de água. O catalisador foi recuperado e reusado no mínimo 4 vezes, mantendo a sua eficiência. Abstract in english N,N',N'',N'''-Tetramethyl tetra-2,3-pyridinoporphyrazinato copper(II) methyl sulfate ([Cu(2,3-tmtppa)](MeSO4)4) efficiently catalyzed the direct conversion of nitriles to N-substituted amides. The one pot selective synthesis of the N-substituted amides from nitriles and primary amines was performed in refluxing H2O. The catalyst was recovered and reused at least four times, maintaining its efficiency.

Ghodsinia, Sara S. E.; Akhlaghinia, Batool; Safaei, Elham; Eshghi, Hossein

2013-06-01

183

Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides.  

UK PubMed Central (United Kingdom)

The synthesis of potassium trifluoro(N-methylheteroaryl)borates and their use in cross-coupling reactions with various aryl and heteroaryl halides to construct N-methyl heteroaryl-substituted aromatic and heteroaromatic compounds are reported.

Molander GA; Ryu D; Hosseini-Sarvari M; Devulapally R; Seapy DG

2013-07-01

184

Contributions to the chemistry of N-substituted metal amides. 11  

International Nuclear Information System (INIS)

[en] ClV(N(C2H5)2)3 and LiR react in aliphatic hydrocarbons to form compounds of the type RV(N(C2H5)2)3 (R = n-C3H7 u. n-C4H9). Reactivity, thermal, magnetical, and catalytical behaviour are described and the results of infrared and mass spectroscopical investigations are communicated. (author)

1979-01-01

185

Selective, nickel-catalyzed hydrogenolysis of aryl ethers.  

UK PubMed Central (United Kingdom)

Selective hydrogenolysis of the aromatic carbon-oxygen (C-O) bonds in aryl ethers is an unsolved synthetic problem important for the generation of fuels and chemical feedstocks from biomass and for the liquefaction of coal. Currently, the hydrogenolysis of aromatic C-O bonds requires heterogeneous catalysts that operate at high temperature and pressure and lead to a mixture of products from competing hydrogenolysis of aliphatic C-O bonds and hydrogenation of the arene. Here, we report hydrogenolyses of aromatic C-O bonds in alkyl aryl and diaryl ethers that form exclusively arenes and alcohols. This process is catalyzed by a soluble nickel carbene complex under just 1 bar of hydrogen at temperatures of 80 to 120°C; the relative reactivity of ether substrates scale as Ar-OAr>>Ar-OMe>ArCH(2)-OMe (Ar, Aryl; Me, Methyl). Hydrogenolysis of lignin model compounds highlights the potential of this approach for the conversion of refractory aryl ether biopolymers to hydrocarbons.

Sergeev AG; Hartwig JF

2011-04-01

186

Improvement of ?1 receptor affinity by late-stage C-H-bond arylation of spirocyclic lactones.  

UK PubMed Central (United Kingdom)

The direct C-H-bond arylation of the complex spirocyclic lactones 13, 14, and 18 allows the introduction of diverse aryl moieties in the last step of the synthesis. A selective ?-arylation of the thiophene moiety was performed with the catalytic system PdCl2/2,2'-bipyridyl/Ag2CO3, whereas the ?-position of the thiophene ring was addressed by using the alternative catalytic system PdCl2/P[OCH(CF3)2]3/Ag2CO3. Due to electronic and steric reasons the arylation of the five-membered lactone 18 occurred in both ?-positions providing 4'-mono-, 6'-mono- and 4',6'-diarylated thiophenes 22-26a-c. Compounds with an additional aryl moiety at the 'upper left (top)' position (1'-position of 13, 3'-position of 14, 4'-position of 18) showed increased ?1 affinity compared to the non-arylated parent compounds. A phenyl moiety at the 'left' position (2'-position in 20a) also increased the ?1 affinity but to a lower extent. A considerable reduction of ?1 affinity was observed after introducing an aryl moiety in 6'-position of 18, which might result from shielding the tertiary amine, which is crucial for interaction with the ?1 receptor. The discussion of the experimental results is supported by high-level quantum chemical DFT-calculations of the NBO-charges of 13 and 18 and the relative energies of the related arylated products.

Meyer C; Neue B; Schepmann D; Yanagisawa S; Yamaguchi J; Würthwein EU; Itami K; Wünsch B

2013-04-01

187

Selective Amination Reactions of ?-Nitro Aryl and Heteroaryl Enoates.  

UK PubMed Central (United Kingdom)

Highly functionalized tetrasubstituted alkenes were obtained by an unexpected amination reaction promoted by ethyl nosyloxycarbamate on various ?-nitro aryl and heteroaryl enoates. A nitrene is likely the aminating species responsible for the observed insertion reaction leading to (E)-?-amino ?-nitro enoates as the major products, regardless of the substrate configuration. The compounds, bearing two nitrogenous functional groups in different oxidation states, can be regarded as interesting synthons. In contrast, aziridination was observed for ?-nitro alkyl enoates or ?-nitro allylic alcohols.

Fioravanti S; Pellacani L; Vergari MC

2013-08-01

188

Palladium-catalyzed ?-arylation of 2-chloroacetates and 2-chloroacetamides.  

UK PubMed Central (United Kingdom)

A method has been developed for the Pd-catalyzed synthesis of ?-(hetero)aryl esters and amides through a Suzuki-Miyaura cross-coupling reaction. This method avoids the use of strong base, does not necessitate inert or low temperature formation of reagents, and does not require the use of a large excess of organometallic reagent. Utilization of organotrifluoroborate salts as nucleophilic partners allows a variety of functional groups and heterocyclic compounds to be tolerated.

Molander GA; Traister KM; Barcellos T

2013-04-01

189

A new class of pyrazolopyridine nucleus with fluorescent properties, obtained through either a radical or a Pd arylation pathway from N-azinylpyridinium N-aminides.  

UK PubMed Central (United Kingdom)

The synthesis of dipyridopyrazole and pyridopyrazolopyrazine derivatives--both of which incorporate a 3-aryl moiety--can be achieved in moderate yields by intramolecular radical arylation of pyridinium N-aminides using tris(trimethylsilyl)silane and azobisisobutyronitrile. Improved results were obtained on using Pd direct arylation in conjunction with microwave irradiation. A preliminary study into the fluorescent properties of the target compounds is also reported.

Abet V; Nuñez A; Mendicuti F; Burgos C; Alvarez-Builla J

2008-11-01

190

A new class of pyrazolopyridine nucleus with fluorescent properties, obtained through either a radical or a Pd arylation pathway from N-azinylpyridinium N-aminides.  

Science.gov (United States)

The synthesis of dipyridopyrazole and pyridopyrazolopyrazine derivatives--both of which incorporate a 3-aryl moiety--can be achieved in moderate yields by intramolecular radical arylation of pyridinium N-aminides using tris(trimethylsilyl)silane and azobisisobutyronitrile. Improved results were obtained on using Pd direct arylation in conjunction with microwave irradiation. A preliminary study into the fluorescent properties of the target compounds is also reported. PMID:18937415

Abet, Valentina; Nuñez, Araceli; Mendicuti, Francisco; Burgos, Carolina; Alvarez-Builla, Julio

2008-10-21

191

alpha-(2-Pyridine)benzyl aryl ketones as potential hypocholesteremic agents.  

Science.gov (United States)

A series of alpha-(2-pyridine)benzyl aryl ketones were prepared as potential hypocholesteremic agents. The synthesis of these compounds was by conversion of 2-benzylpyridine to its anion with n-butyllithium and condensation of the anion with selected aromatic esters. The ketones were tested for their hypocholesteremic activity in rats, and those compounds showing activity were further tested for estrogenicity. Only those aryl ketones with substituents in the ortho position showed a statistically significant reduction in serum cholesterol. Of these compounds the tert-butyl derivative had the most favorable hypocholesteremic to estrogenic ratio. PMID:722749

Hewitt, L E; Wade, D R; Sinsheimer, J E; Wang, J H; Drach, J C; Burckhalter, J H

1978-12-01

192

alpha-(2-Pyridine)benzyl aryl ketones as potential hypocholesteremic agents.  

UK PubMed Central (United Kingdom)

A series of alpha-(2-pyridine)benzyl aryl ketones were prepared as potential hypocholesteremic agents. The synthesis of these compounds was by conversion of 2-benzylpyridine to its anion with n-butyllithium and condensation of the anion with selected aromatic esters. The ketones were tested for their hypocholesteremic activity in rats, and those compounds showing activity were further tested for estrogenicity. Only those aryl ketones with substituents in the ortho position showed a statistically significant reduction in serum cholesterol. Of these compounds the tert-butyl derivative had the most favorable hypocholesteremic to estrogenic ratio.

Hewitt LE; Wade DR; Sinsheimer JE; Wang JH; Drach JC; Burckhalter JH

1978-12-01

193

[N-substituted p-fluorobenzene sulfonamides with antimicrobial activity. I  

UK PubMed Central (United Kingdom)

In an extension of the investigations on fluorine derivatives of potential pharmacological interest, some new p-fluorobenzensulfonanilides were synthesized and screened in vitro against many species of Gram-positive and Gram-negative bacteria and against some strains of Candida albicans. Some of these compounds exhibited significant antibacterial activity. The relation between activity and structure revealed that the presence of chloro and trifluoromethyl groups in the aniline ring increases activity against Gram-positive bacteria. The acute toxicity in mice was also determined.

Vigorita MG; Saporito G; Pizzimenti FC

1984-06-01

194

2-(substituted phenyl)-2-(4,5,6,7-thiophane[3,2-c] pyridine-5(4H)-group)-N-substitute-acetamide as well as preparation method and application thereof  

UK PubMed Central (United Kingdom)

The invention belongs to the technical field of malignant tumor resistant medicaments and provides 2-(substituted phenyl)-2-(4,5,6,7-thiophane[3,2-c] pyridine-5(4H)-group)-N-substitute-acetamide with a structure of a general formula I and a pharmaceutically acceptable salt thereof, wherein R is hydrogen, a C1-C3 straight chain or a branched alkyl group and R1 and R2 are hydrogen, C1-C3 straight chains or branched alkyl groups, halogens, halogenated methyl groups and C1-C3 alkoxyl groups. The invention also relates to a preparation method of the compound and also discloses a medical composition using the compound or the pharmaceutically acceptable salt thereof as an active and effective constituent and application thereof as malignant tumor resistant medicaments.

MEI BAI; JIFANG CHEN; BINGNI LIU; DENGKE LIU; MO LIU; YING LIU; SHUAI MU; JINGYANG WANG

195

Polymeric media comprising polybenzimidazoles N-substituted with organic-inorganic hybrid moiety  

Energy Technology Data Exchange (ETDEWEB)

A PBI compound includes imidazole nitrogens at least a portion of which are substituted with an organic-inorganic hybrid moiety may be included in a separatory medium. At least 85% of the imidazole nitrogens may be substituted. The organic-inorganic hybrid moiety may be an organosilane moiety, for example, (R)Me.sub.2SiCH.sub.2-- where R is selected from among methyl, phenyl, vinyl, and allyl. The separatory medium may exhibit an H.sub.2, Ar, N.sub.2, O.sub.2, CH.sub.3, or CO.sub.2 gas permeability greater than the gas permeability of a comparable separatory medium comprising the PBI compound without substitution. The separatory medium may further include an electronically conductive medium and/or an ionically conductive medium. The separatory medium may be used as a membrane (semi-permeable, permeable, and non-permeable), a barrier, an ion exchange media, a filter, a gas chromatography coating (such as stationary phase coating in affinity chromatography), etc.

Klaehn, John R. (Idaho Falls, ID); Peterson, Eric S. (Idaho Falls, ID); Wertsching, Alan K. (Idaho Falls, ID); Orme, Christopher J. (Shelley, ID); Luther, Thomas A. (Idaho Falls, ID); Jones, Michael G. (Pocatello, ID)

2009-12-15

196

COMPOUNDS  

UK PubMed Central (United Kingdom)

The present invention provides a compound of formula (I') which is a nystatin derivative having an additional double bond present between C28 and C29 and which is further modified relative to nystatin at one or more of positions C5, C7, C9, C10, C11, C16 or at the amino group of mycosamine. These compounds are used as anti-fungal agents.

ZOTCHEV SERGEY BORISOVICH; BORGOS SVEN EVEN FINN; BRAUTASET TRYGVE; ELLINGSEN TROND ERLING; OLSUFYEVA EVGENIA NIKOLAEVNA; PREOBRAZHENSKAYA MARIA NIKOLAEVNA; SLETTA HAVARD

197

Stereoisomers of N-substituted soft anticholinergics and their zwitterionic metabolite based on glycopyrrolate--syntheses and pharmacological evaluations.  

UK PubMed Central (United Kingdom)

PURPOSE: In this study, isomers of two N-substituted soft anticholinergics based on glycopyrrolate, SGM (PcPOAGP_NA.Me) and SGE (PcPOAGP_NA.Et) [3'-(2-cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1'-methyl-1'-alkoxycarbonylpyrrolidinium bromide] and their zwitterionic metabolite, SGa (PcPOAGP_NA.H) [3'-(2-cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1'-methyl-1'-carboxymethylpyrrolidinium inner salt] were synthesized and their pharmacological activities were evaluated in vitro and in vivo. METHODS: The isomers of SGM and SGE were synthesized with both optically pure methyl-cyclopentylmandelate and 3-hydroxy-N-methylpyrrolidine. Trans-esterification followed by quarternization with alkyl bromoacetate gave four isomers of SGM or SGE with the nitrogen chiral center unresolved (2R3'S-SGM, 2R3'R-SGM, 2S3'S-SGM, 2S3'R-SGM or 2R3'S-SGE, 2R3'R-SGE, 2S3'S-SGE, 2S3'R-SGE). The hydrolysis of these four isomers followed by HPLC separation resulted in eight fully resolved isomers of SGa (2R3'R1'R, 2R3'S1'R, 2R3'R1'S, 2R3'S1'S, 2S3'R1'R, 2S3'S1'R, 2S3'R1'S, and 2S3'S1'S). Pharmacological activities were assessed by using in vitro receptor-binding assay and guinea pig ileum pA2-assay, and by evaluating the in vivo rabbit mydriatic effects. Results were compared to those obtained with conventional anticholinergic agents, such as glycopyrrolate, N-meythylscopolamine, and tropicamide, as well as those obtained with previously prepared racemic mixtures and 2R isomers. RESULTS: Receptor binding pKi values at cloned human muscarinic receptors (M1-M4 subtypes) were in the 6.0-9.5 range for the newly synthesized SGM and SGE isomers, and in the 5.0-8.6 range for the SGa isomers. In all cases, 2R isomers were significantly more active than 2S isomers (27 to 447 times for SGM isomers, and 6 to 4467 times for SGa isomers). Among the four SGM isomers with unresolved 1' (N) chiral center, the 3'R isomers were more active than the corresponding 3'S isomers (1.5-12.9 times), whereas, among the SGa isomers, the 3'S isomers were not always more active than the corresponding 3'R isomers indicating that activity determined based on configuration at chiral center 3' is significantly affected by the configuration of the other two chiral centers, 2 and 1'. Among the completely resolved eight SGa isomers (all three chiral centers resolved), 1'S isomers were always more active than the corresponding 1'R isomers (1.8-22.4 times). Results also indicate that some isomers showed good M3/M2 muscarinic-receptor subtype-selectivity (about 3-5 times), and 2R and 3'S were the determining configurations for this property. Guinea pig ileum assays and rabbit mydriasis tests on SGa isomers further confirmed the stereospecificity. In rabbit eyes, some 2R-SGa isomers showed mydriatic potencies similar to glycopyrrolate and exceeded tropicamide, but their mydriatic effects lasted considerably shorter, and they did not induce dilation of the pupil in the contralateral, water-treated eye. These results indicate that these compounds are locally active, but safe and have a low potential to cause systemic side effects. The pharmacological potency of the eight SGa isomers was estimated as 2R3'S1'S approximately equal to 2R3'R1'S approximately equal to 2R3'S1'R > 2R3'R1'R > 2S3'R1'S > 2S3'S1'S approximately equal to 2S3'R1'R > 2S3'S1'R (p < 0.05). CONCLUSIONS: The stereospecificity and M3/M2 muscarinic-receptor subtype-selectivity of soft anticholinergics, SGM, SGE, and SGa have been demonstrated. In agreement with previous results, the potential for their effective and safe use has been confirmed.

Wu WM; Wu J; Mori N; Buchwald P; Bodor N

2008-03-01

198

N-SUBSTITUTION AND á1-ADRENERGIC RECEPTOR AFFINITY OF LAUDANOSINE ANALOGUES  

Directory of Open Access Journals (Sweden)

Full Text Available Benzyltetrahydroisoquinoline (BTHIQ) molecules are able to adopt widely differing conformations that depend on the presence or absence of N-substituents. To assess the possible role of BTHIQ conformation on the affinity of these compounds for a 1-adrenergic receptors, of interest for the management of hypertension, the racemic N-unsubstituted BTHIQ norlaudanosine and a series of N-alkylated derivatives were assessed for binding to rat brain cortical sites labelled with the radioligand [³H]prazosin. The a 1-adrenergic affinity in this series increased with the bulk of the substituent on the nitrogen atom, from the N-ethyl to the N-propyl analogue. Comparison of these results with published data for related BTHIQs and for the rigid mimics of the fully extended and semi-folded conformations of laudanosine, tetrahydropalmatine and glaucine, suggested that the a 1-adrenergic receptor binding site is able to accommodate either conformation. The presence of a bulky substituent on the nitrogen atom seems to favor receptor binding independently of the favored conformation, and that the orientation in which BTHIQs are bound probably differs depending on the presence or absence of a hydroxyl group at a key position

PATRICIO ITURRIAGA-VÁSQUEZ; BRUCE K CASSELS; M. DOLORES IVORRA; M. PILAR D'OCON

2006-01-01

199

N-SUBSTITUTION AND á1-ADRENERGIC RECEPTOR AFFINITY OF LAUDANOSINE ANALOGUES  

Scientific Electronic Library Online (English)

Full Text Available Abstract in english Benzyltetrahydroisoquinoline (BTHIQ) molecules are able to adopt widely differing conformations that depend on the presence or absence of N-substituents. To assess the possible role of BTHIQ conformation on the affinity of these compounds for a 1-adrenergic receptors, of interest for the management of hypertension, the racemic N-unsubstituted BTHIQ norlaudanosine and a series of N-alkylated derivatives were assessed for binding to rat brain cortical sites labelled with th (more) e radioligand [³H]prazosin. The a 1-adrenergic affinity in this series increased with the bulk of the substituent on the nitrogen atom, from the N-ethyl to the N-propyl analogue. Comparison of these results with published data for related BTHIQs and for the rigid mimics of the fully extended and semi-folded conformations of laudanosine, tetrahydropalmatine and glaucine, suggested that the a 1-adrenergic receptor binding site is able to accommodate either conformation. The presence of a bulky substituent on the nitrogen atom seems to favor receptor binding independently of the favored conformation, and that the orientation in which BTHIQs are bound probably differs depending on the presence or absence of a hydroxyl group at a key position

ITURRIAGA-VÁSQUEZ, PATRICIO; CASSELS, BRUCE K; IVORRA, M. DOLORES; D'OCON, M. PILAR

2006-09-01

200

Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents  

Directory of Open Access Journals (Sweden)

Full Text Available This study reports the synthesis of some substituted 5-iodouracils and their bioactivities. Alkylation of 5-iodouracils gave predominately N1-substituted-(R)-5-iodouracil compounds 7a-d (R = n-C4H9, s-C4H9, CH2C6H11, CH2C6H5) together with N1,N3-disubstituted (R) analogs 8a-b (R = n-C4H9, CH2C6H11). Their antimicrobial activity was tested against 27 strains of microorganisms using the agar dilution method. The analogs 7a, 7c and 7d displayed 25-50% inhibition against Branhamella catarrhalis, Neisseria mucosa and Streptococcus pyogenes at 0.128 mg/mL. No antimalarial activity was detected for any of the analogs when tested against Plasmodium falciparum (T9.94). Their anticancer activity was also examined. Cyclohexylmethyl analogs 7c and 8b inhibited the growth of HepG2 cells. Significantly, N1,N3-dicyclohexylmethyl analog 8b displayed the most potent anticancer activity, with an IC50 of 16.5 mg/mL. These 5-iodouracil analogs represent a new group of anticancer and antibacterial agents with potential for development for medicinal applications.

Supaluk Prachayasittikul; Nirun Sornsongkhram; Ratchanok Pingaew; Apilak Worachartcheewan; Somsak Ruchirawat; Virapong Prachayasittikul

2009-01-01

 
 
 
 
201

Auxiliary-enabled Pd-catalyzed direct arylation of methylene C(sp3)-H bond of cyclopropanes: highly diastereoselective assembling of di- and trisubstituted cyclopropanecarboxamides.  

UK PubMed Central (United Kingdom)

An auxiliary-enabled and Pd(OAc)2-catalyzed direct arylation of C(sp(3))-H bonds of cyclopropanes and production of di- and trisubstituted cyclopropanecarboxamides having contiguous stereocenters are reported. The installation of aryl groups on cyclopropanecarboxamides led to the assembling of novel mono- and di- aryl-N-(quinolin-8-yl)cyclopropanecarboxamide scaffolds and mono- and di- aryl-N-(2-(methylthio)phenyl)cyclopropanecarboxamides. The stereochemistry of products was unequivocally assigned from the X-ray structures of key compounds.

Parella R; Gopalakrishnan B; Babu SA

2013-07-01

202

Auxiliary-enabled Pd-catalyzed direct arylation of methylene C(sp3)-H bond of cyclopropanes: highly diastereoselective assembling of di- and trisubstituted cyclopropanecarboxamides.  

Science.gov (United States)

An auxiliary-enabled and Pd(OAc)2-catalyzed direct arylation of C(sp(3))-H bonds of cyclopropanes and production of di- and trisubstituted cyclopropanecarboxamides having contiguous stereocenters are reported. The installation of aryl groups on cyclopropanecarboxamides led to the assembling of novel mono- and di- aryl-N-(quinolin-8-yl)cyclopropanecarboxamide scaffolds and mono- and di- aryl-N-(2-(methylthio)phenyl)cyclopropanecarboxamides. The stereochemistry of products was unequivocally assigned from the X-ray structures of key compounds. PMID:23772812

Parella, Ramarao; Gopalakrishnan, Bojan; Babu, Srinivasarao Arulananda

2013-06-17

203

Visible-light photoredox in homolytic aromatic substitution: direct arylation of arenes with aryl halides.  

Science.gov (United States)

Direct arylation of unactivated arenes or heteroarenes with aryl halides could be carried out in the presence of potassium tert-butoxide and dimethyl sulfoxide under visible-light irradiation. Ir(ppy)3 was found to be an effective photoredox catalyst for this reaction. The reactions of aryl iodides occurred at room temperature. Elevated temperature was required for aryl bromides. Homolytic aromatic substitution was proposed to be the operative reaction pathway. PMID:23688041

Cheng, Yannan; Gu, Xiangyong; Li, Pixu

2013-05-21

204

Double arylation of allyl alcohol via a one-pot Heck arylation-isomerization-acylation cascade.  

UK PubMed Central (United Kingdom)

A one-pot, two-step catalytic protocol has been developed. A regioselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones.

Colbon P; Ruan J; Purdie M; Mulholland K; Xiao J

2011-10-01

205

Double arylation of allyl alcohol via a one-pot Heck arylation-isomerization-acylation cascade.  

Science.gov (United States)

A one-pot, two-step catalytic protocol has been developed. A regioselective Heck coupling between aryl bromides and allyl alcohol leads to the generation of arylated allyl alcohols that in situ isomerize to give aldehydes, which then undergo an acylation reaction with a second aryl bromide. A variety of aryl bromides can be employed in both the initial Heck reaction and the acylation, providing easy access to a wide variety of substituted dihydrochalcones. PMID:21932768

Colbon, Paul; Ruan, Jiwu; Purdie, Mark; Mulholland, Keith; Xiao, Jianliang

2011-09-20

206

Visible-light photoredox in homolytic aromatic substitution: direct arylation of arenes with aryl halides.  

UK PubMed Central (United Kingdom)

Direct arylation of unactivated arenes or heteroarenes with aryl halides could be carried out in the presence of potassium tert-butoxide and dimethyl sulfoxide under visible-light irradiation. Ir(ppy)3 was found to be an effective photoredox catalyst for this reaction. The reactions of aryl iodides occurred at room temperature. Elevated temperature was required for aryl bromides. Homolytic aromatic substitution was proposed to be the operative reaction pathway.

Cheng Y; Gu X; Li P

2013-06-01

207

Consecutive Three-Component Synthesis of 3-(Hetero)Aryl-1H-pyrazoles with Propynal Diethylacetal as a Three-Carbon Building Block  

Directory of Open Access Journals (Sweden)

Full Text Available A novel consecutive three-component synthesis of 3-(hetero)aryl-1H-pyrazoles via room temperature Sonogashira arylation of propynal diethylacetal used as a propargyl aldehyde synthetic equivalent has been disclosed. The final acetal cleavage-cyclocondensation with hydrazine hydrochloride at 80 °C rapidly furnishes the title compounds in a one-pot fashion.

Lucilla Levi; Christina Boersch; Charlotte F. Gers; Eugen Merkul; Thomas J. J. Müller

2011-01-01

208

Targeting of Aryl Hydrocarbon Receptor-Mediated Activation of Cyclooxygenase-2 Expression by the Indole-3-Carbinol Metabolite 3,3?-Diindolylmethane in Breast Cancer Cells12  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Ligands of the aryl hydrocarbon receptor (AhR) include the environmental xenobiotic 2,3,7,8 tetrachlorodibenzo(p)dioxin (TCDD), polycyclic aryl hydrocarbons, and the dietary compounds 3, 3?-diindolylmethane (DIM), a condensation product of indol-3-carbinol found in Brassica vegetables, and the phyto...

Degner, Stephanie C.; Papoutsis, Andreas J.; Selmin, Ornella; Romagnolo, Donato F.

209

Direct arylation of meso-formyl porphyrin.  

UK PubMed Central (United Kingdom)

Palladium-catalyzed direct arylation of meso-formyl Ni(II) porphyrin with aryl bromides provided ?-monoarylated meso-formyl porphyrins. In spite of the existence of the meso-formyl group, the reactions proceeded regioselectively at the ?-position adjacent to the formyl group. ?-Arylated formyl porphyrin was converted to a tetraline-fused porphyrin by reduction and subsequent acid-catalyzed cyclization and to a meso-meso vinylene-bridged diporphyrin by McMurry coupling (see scheme).

Tokuji S; Awane H; Yorimitsu H; Osuka A

2013-01-01

210

Synthesis, characterization and antiproliferative activity of ?-aryl-?-iodo-?-lactones  

Science.gov (United States)

A convenient pathway for the synthesis of new of ?-aryl-?-iodo-?-lactones is described. The synthetic route led to both cis and trans isomers which were separated by column chromatography or crystallization. The structures of synthesized compounds were confirmed by spectroscopic methods: IR, NMR and HR-MS. For lactones with naphthyl ring (6e and 7e) the crystal structures were also obtained. The lactones were screened for biological evaluation against cancer line HL-60 (human promyelocytic leukemia). The tests showed that the presence of substituent at the benzene ring does not significantly affect the antiproliferative activity of the compound.

Wzorek, Alicja; Gawdzik, Barbara; G?adkowski, Witold; Urbaniak, Mariusz; Bara?ska, Anita; Mali?ska, Maura; Wo?niak, Krzysztof; Kempi?ska, Katarzyna; Wietrzyk, Joanna

2013-09-01

211

Palladium-Catalyzed Direct Intermolecular ?-Arylation of Amides with Aryl Chlorides.  

UK PubMed Central (United Kingdom)

An efficient catalytic system for the direct intermolecular ?-arylation of acetamide derivatives with aryl chlorides is presented. Chemoselectivities up to 10:1 in the mono- and diarylation of acetamides were achieved by careful selection of bases, solvents, and stoichiometry. Bis-arylated amides were prepared in up to 95% yield.

Zheng B; Jia T; Walsh PJ

2013-08-01

212

Palladacycle-Catalyzed Deacetonative Sonogashira Coupling of Aryl Propargyl Alcohols with Aryl Chlorides.  

UK PubMed Central (United Kingdom)

An efficient and general protocol for the deacetonative Sonogashira coupling of aryl propargyl alcohols with aryl chlorides has been described. The reaction could proceed smoothly with the catalyst system of palladacycle/Xphos. Note that this result represents the first successful deacetonative Sonogashira version for electron-poor, electron-neutral and even inactive sterically hindered electron-rich aryl chlorides.

Hu H; Yang F; Wu Y

2013-09-01

213

Naphthalene bisimides asymmetrically and symmetrically N-substituted with triarylamine--comparison of spectroscopic, electrochemical, electronic and self-assembly properties.  

UK PubMed Central (United Kingdom)

Two semiconducting naphthalene bisimides were comparatively studied: NBI-(TAA)(2), symmetrically N-substituted with triaryl amine and asymmetric NBI-TAA-Oc with triaryl amine and octyl N-substituents. Both compounds show very similar spectroscopic and redox properties but differ in their supramolecular organization. As evidenced by STM, in monolayers on HOPG they form ordered 2D structures, however of different packing patterns. NBI-(TAA)(2) does not form ordered 3D structures, yielding amorphous thin films whereas films of NBI-TAA-Oc are highly crystalline. DFT calculations predict the ionization potential (IP) of 5.22 eV and 5.18 eV for NBI-TAA-Oc and NBI-(TAA)(2), respectively, as well as the electron affinity values (EA) of -3.25 eV and -3.22 eV. These results are consistent with the cyclic voltammetry data which yield similar values of IP (5.20 eV and 5.19 eV) and somehow different values of EA (-3.80 eV and -3.83 eV). As judged from these data, both semiconductors should exhibit ambipolar behavior. Indeed, NBI-TAA-Oc is ambipolar, showing hole and electron mobilities of 4.5 × 10(-5) cm(2)/(V s) and of 2.6 × 10(-4) cm(2)/(V s), respectively, in the field effect transistor configuration. NBI-(TAA)(2) is not ambipolar and yields field effect only in the p-channel configuration. This different behavior is rationalized on the basis of structural factors.

Rybakiewicz R; Zapala J; Djurado D; Nowakowski R; Toman P; Pfleger J; Verilhac JM; Zagorska M; Pron A

2013-02-01

214

Naphthalene bisimides asymmetrically and symmetrically N-substituted with triarylamine--comparison of spectroscopic, electrochemical, electronic and self-assembly properties.  

Science.gov (United States)

Two semiconducting naphthalene bisimides were comparatively studied: NBI-(TAA)(2), symmetrically N-substituted with triaryl amine and asymmetric NBI-TAA-Oc with triaryl amine and octyl N-substituents. Both compounds show very similar spectroscopic and redox properties but differ in their supramolecular organization. As evidenced by STM, in monolayers on HOPG they form ordered 2D structures, however of different packing patterns. NBI-(TAA)(2) does not form ordered 3D structures, yielding amorphous thin films whereas films of NBI-TAA-Oc are highly crystalline. DFT calculations predict the ionization potential (IP) of 5.22 eV and 5.18 eV for NBI-TAA-Oc and NBI-(TAA)(2), respectively, as well as the electron affinity values (EA) of -3.25 eV and -3.22 eV. These results are consistent with the cyclic voltammetry data which yield similar values of IP (5.20 eV and 5.19 eV) and somehow different values of EA (-3.80 eV and -3.83 eV). As judged from these data, both semiconductors should exhibit ambipolar behavior. Indeed, NBI-TAA-Oc is ambipolar, showing hole and electron mobilities of 4.5 × 10(-5) cm(2)/(V s) and of 2.6 × 10(-4) cm(2)/(V s), respectively, in the field effect transistor configuration. NBI-(TAA)(2) is not ambipolar and yields field effect only in the p-channel configuration. This different behavior is rationalized on the basis of structural factors. PMID:23243662

Rybakiewicz, Renata; Zapala, Joanna; Djurado, David; Nowakowski, Robert; Toman, Petr; Pfleger, Jiri; Verilhac, Jean-Marie; Zagorska, Malgorzata; Pron, Adam

2013-02-01

215

Pd-Xantphos-catalyzed direct arylation of nucleosides.  

UK PubMed Central (United Kingdom)

Direct arylation of the exocyclic amino groups of nucleosides represents a simple approach to N-aryl nucleoside derivatives. To date, one limitation has been that only electron-deficient aryl bromides and triflates possessed adequate reactivity for efficient, direct N-arylation of nucleosides. We demonstrate herein that Pd-Xantphos catalytic systems lead to successful N-arylation of suitably protected 2'-deoxyadenosine and 2'-deoxyguanosine with a wide range of aryl bromides.

Ngassa FN; Dekorver KA; Melistas TS; Yeh EA; Lakshman MK

2006-09-01

216

Pd-Xantphos-catalyzed direct arylation of nucleosides.  

Science.gov (United States)

Direct arylation of the exocyclic amino groups of nucleosides represents a simple approach to N-aryl nucleoside derivatives. To date, one limitation has been that only electron-deficient aryl bromides and triflates possessed adequate reactivity for efficient, direct N-arylation of nucleosides. We demonstrate herein that Pd-Xantphos catalytic systems lead to successful N-arylation of suitably protected 2'-deoxyadenosine and 2'-deoxyguanosine with a wide range of aryl bromides. PMID:16986963

Ngassa, Felix N; Dekorver, Kyle A; Melistas, Theothora S; Yeh, Edmund A-H; Lakshman, Mahesh K

2006-09-28

217

(HET)ARYL-P-QUINONE DERIVATIVES FOR TREATMENT OF MITOCHONDRIAL DISEASES  

UK PubMed Central (United Kingdom)

Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Kearns-Sayre Syndrome (KSS), are disclosed, as well as compounds useful in the methods of the invention, such as 2-(3-hydroxy-3-methyl-butyl)-6-(het)aryl-p-quinone or as 2-(3-hydroxy-3-methylbutyl)-3-(het)aryl-p-quinone derivatives. Energy biomarkers useful in assessing the metabolic state of a subject and the efficacy of treatment are also disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods, are also disclosed.

HIINMAN ANDREW W; WESSON KIERON E

218

A survey of the cleavage of aryl-metal bonds by elemental fluorine  

International Nuclear Information System (INIS)

The reaction of elemental fluorine with phenyl derivatives of tin, lead, germanium, silicon, mercury, and thallium has been studied with the aim of developing a general method for labelling aromatic compounds with radioactive 18F. Rapid synthesis of fluorobenzene was achieved in varying chemical yields up to 70 percent, depending largely upon the metal substrate used, with aryl-tin compounds giving the highest yields. Radiochemical yields are also given for the synthesis of 18/F-fluoro-benzene from the cleavage of aryl-tin bonds with 18F-F2

1982-01-01

219

Design and synthesis of 2-N-substituted indazolone derivatives as non-carboxylic acid glycogen synthase activators.  

UK PubMed Central (United Kingdom)

Glycogen synthase (GS) catalyzes the transfer of glucose residues from UDP-glucose to a glycogen polymer chain, a critical step for glucose storage. Patients with type 2 diabetes normally exhibit low glycogen levels and decreased muscle glucose uptake is the major defect in whole body glucose disposal. Therefore, activating GS may provide a potential approach for the treatment of type 2 diabetes. In order to identify non-carboxylic acids GS activators, we designed and synthesized a series of 2-N-alkyl- and 2-N-aryl-indazolone derivatives and studied their activity in activating human GS.

Qian Y; Bolin D; Conde-Knape K; Gillespie P; Hayden S; Huang KS; Olivier AR; Sato T; Xiang Q; Yun W; Zhang X

2013-05-01

220

COMPOUNDS  

UK PubMed Central (United Kingdom)

Described is a compound of formula (I): where R4 represents -RA-L-Ar1, formula (II): or R3 together with R4 and the nitrogen to which they are attached form a 5 or 6 membered heterocyclic group optionally including a further heteroatom selected from N, O or S, wherein said heterocyclic group is substituted by one or two specified groups, and Z, R1, R2, R5, RA, L and Ar1 are further defined.

WADMAN SJOERD NICOLAAS

 
 
 
 
221

1-Aryl-4-silylmethyl[60]fullerenes: synthesis, properties, and photovoltaic performance.  

Science.gov (United States)

The efficient nucleophilic addition of aryl Grignard reagents (aryl=4-MeOC(6)H(4), 4-Me(2)NC(6)H(4), Ph, 4-CF(3)C(6)H(4), and thienyl) to C(60) in the presence of DMSO produced 1,2-arylhydro[60]fullerenes after acid treatment. The reactions of the anions of these arylhydro[60]fullerenes with either dimethylphenylsilylmethyl iodide or dimethyl(2-isopropoxyphenyl)silylmethyl iodide yielded the target compounds, 1-aryl-4-silylmethyl[60]fullerenes. The properties and structures of these 1-aryl-4-silylmethyl[60]fullerenes (aryl=4-MeOC(6)H(4), thienyl) were examined by electrochemical studies, X-ray crystallography, flash-photolysis time-resolved microwave-conductivity (FP-TRMC) measurements, and electron-mobility measurements by using a space-charge-limited current (SCLC) model. Organic photovoltaic devices with a polymer-based bulk heterojunction structure and small-molecule-based p-n and p-i-n heterojunction configurations were fabricated by using 1-aryl-4-silylmethyl[60]fullerenes as an electron acceptor. The most efficient device exhibited a power-conversion efficiency of 3.4% (short-circuit current density: 8.1 mA/cm(2), open-circuit voltage: 0.69 V, fill factor: 0.59). PMID:23023947

Matsuo, Yutaka; Oyama, Hiromi; Soga, Iwao; Okamoto, Toshihiro; Tanaka, Hideyuki; Saeki, Akinori; Seki, Shu; Nakamura, Eiichi

2012-09-28

222

Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines.  

UK PubMed Central (United Kingdom)

The palladium-catalyzed tandem arylation of O-homoallylhydroxylamines with 2 equiv of aryl bromides was examined. With Pd2(dba)3 (1 mol %) as the catalyst, Xantphos (2 mol %) as the ligand, and NaOt-Bu as the base, the reactions of O-homoallylhydroxylamines with aryl bromides via sequential N-arylation/cyclization/C-arylation in toluene afforded the corresponding N-aryl-3-arylmethylisoxazolidines in good yields with excellent diastereoselectivity.

Peng J; Lin W; Yuan S; Chen Y

2007-04-01

223

Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines.  

Science.gov (United States)

The palladium-catalyzed tandem arylation of O-homoallylhydroxylamines with 2 equiv of aryl bromides was examined. With Pd2(dba)3 (1 mol %) as the catalyst, Xantphos (2 mol %) as the ligand, and NaOt-Bu as the base, the reactions of O-homoallylhydroxylamines with aryl bromides via sequential N-arylation/cyclization/C-arylation in toluene afforded the corresponding N-aryl-3-arylmethylisoxazolidines in good yields with excellent diastereoselectivity. PMID:17367194

Peng, Jinsong; Lin, Wenqing; Yuan, Shixue; Chen, Yuanwei

2007-03-17

224

Effects of pesticide compounds (chlorothalonil and mancozeb) and benzo[a]pyrene mixture on aryl hydrocarbon receptor, p53 and ubiquitin gene expression levels in haemocytes of soft-shell clams (Mya arenaria).  

Science.gov (United States)

The aim of this study is to investigate the effects of the pesticides/polycyclic aromatic hydrocarbon mixture on aryl hydrocarbon receptor (AhR), p53 and ubiquitin mRNA level in haemocytes of Mya arenaria exposed to a mixture of chlorothalonil, mancozeb and benzo[a]pyrene (BaP) for 48 and 72 h. AhR, p53 and ubiquitin gene expression levels were quantified using quantitative Real-time PCR. For robust and accurate quantification of transcripts, suitable housekeeping genes were selected from four sets of ribosomal and elongation factors transcripts previously sequenced from Mya arenaria using geNorm open source software. Quantitative Real-time PCR data exhibited a significantly high expression of AhR after 72 h of exposure (P ? 0.05). p53 gene expression seems to be up-regulated by the mixture after 48 h, however not significantly; but the level of p53 mRNA is down-regulated by the xenobiotics between 48 and 72 h after exposure. This study postulates that AhR mRNA levels could be used as an indicator of the exposure of clams' haemocytes to a mixture of xenobiotics such as chlorothalonil, mancozeb and BaP. However, further studies have to be pursued in order to unravel the molecular mechanisms involved in the p53 signaling pathway. PMID:21688059

Pariseau, Julie; McKenna, Patricia; Aboelkhair, Mohammed; Saint-Louis, Richard; Pelletier, Emilien; Davidson, T Jeffrey; Tremblay, Réjean; Berthe, Franck C J; Siah, Ahmed

2011-06-18

225

Effects of pesticide compounds (chlorothalonil and mancozeb) and benzo[a]pyrene mixture on aryl hydrocarbon receptor, p53 and ubiquitin gene expression levels in haemocytes of soft-shell clams (Mya arenaria).  

UK PubMed Central (United Kingdom)

The aim of this study is to investigate the effects of the pesticides/polycyclic aromatic hydrocarbon mixture on aryl hydrocarbon receptor (AhR), p53 and ubiquitin mRNA level in haemocytes of Mya arenaria exposed to a mixture of chlorothalonil, mancozeb and benzo[a]pyrene (BaP) for 48 and 72 h. AhR, p53 and ubiquitin gene expression levels were quantified using quantitative Real-time PCR. For robust and accurate quantification of transcripts, suitable housekeeping genes were selected from four sets of ribosomal and elongation factors transcripts previously sequenced from Mya arenaria using geNorm open source software. Quantitative Real-time PCR data exhibited a significantly high expression of AhR after 72 h of exposure (P ? 0.05). p53 gene expression seems to be up-regulated by the mixture after 48 h, however not significantly; but the level of p53 mRNA is down-regulated by the xenobiotics between 48 and 72 h after exposure. This study postulates that AhR mRNA levels could be used as an indicator of the exposure of clams' haemocytes to a mixture of xenobiotics such as chlorothalonil, mancozeb and BaP. However, further studies have to be pursued in order to unravel the molecular mechanisms involved in the p53 signaling pathway.

Pariseau J; McKenna P; Aboelkhair M; Saint-Louis R; Pelletier E; Davidson TJ; Tremblay R; Berthe FC; Siah A

2011-11-01

226

COMPOUNDS  

UK PubMed Central (United Kingdom)

Described is a compound of formula (I): wherein X represents a bond or an amino acid residue R3 represents H or C1-6 alkyl R4 represents -RA-L-Ar1, or R3 together with R4 and the nitrogen to which they are attached form a 5 or 6 membered heterocyclic group optionally including a further heteroatom selected from N, O or S, wherein said heterocyclic group is substituted by a specified group, and where Z, R1, R2, R5, RA, L and Ar1 are further defined.

WADMAN SJOERD NICOLAAS

227

COMPOUNDS  

UK PubMed Central (United Kingdom)

Described is a compound of formula (I): wherein X represents a bond or an amino acid residue R3 represents H or C1-6 alkyl R4 represents -RA-L-Ar1, or R3 together with R4 and the nitrogen to which they are attached form a 5 or 6 membered heterocyclic group optionally including a further heteroatom selected from N, O or S, wherein said heterocyclic group is substituted by YAr1, where Z, R1, R2, R5, RA, L, Ar1 and Y are further defined.

WADMAN SJOERD NICOLAAS

228

Discovery of 4-Aryl-2-benzoyl-imidazoles as tubulin polymerization inhibitor with potent antiproliferative properties.  

UK PubMed Central (United Kingdom)

A series of 4-aryl-2-benzoyl-imidazoles were designed and synthesized based on our previously reported 2-aryl-4-benzoyl-imidazole (ABI) derivatives. The new structures reversed the aryl group and the benzoyl group of previous ABI structures and were named as reverse ABI (RABI) analogues. RABIs were evaluated for biological activity against eight cancer cell lines including multidrug-resistant cancer cell lines. In vitro assays indicated that several RABI compounds had excellent antiproliferative properties, with IC50 values in the low nanomolar range. The average IC50 of the most active compound 12a is 14 nM. In addition, the mechanism of action of these new analogues was investigated by cell cycle analysis, tubulin polymerization assay, competitive mass spectrometry binding assay, and molecular docking studies. These studies confirmed that these new RABI analogues maintain their mechanisms of action by disrupting tubulin polymerization, similar to their parental ABI analogues.

Xiao M; Ahn S; Wang J; Chen J; Miller DD; Dalton JT; Li W

2013-04-01

229

Benzyne arylation of oxathiane glycosyl donors  

Directory of Open Access Journals (Sweden)

Full Text Available The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford ?-glycosyl acetates in a ‘one-pot’ reaction, even in the presence of alternative acceptor alcohols.

Martin A. Fascione; W. Bruce Turnbull

2010-01-01

230

Synthesis of functionalized pseudopeptides through five-component sequential Ugi/nucleophilic reaction of N-substituted 2-alkynamides with hydrazides.  

UK PubMed Central (United Kingdom)

Five-component sequential Ugi/nucleophilic addition reaction of aromatic aldehydes, primary amines, propiolic acid, isocyanides, and hydrazides has been developed in order to access polyfunctional pseudopeptides. The reaction may proceed through formation of N-substituted 2-alkynamides as intermediates. This process is found to be mild and operationally simple with broad substrate scope.

Maghari S; Ramezanpour S; Balalaie S; Darvish F; Rominger F; Bijanzadeh HR

2013-07-01

231

Effects of N-phenylpropyl-N'-substituted piperazine sigma receptor ligands on cocaine-induced hyperactivity in mice.  

UK PubMed Central (United Kingdom)

The present study examined N-phenylpropyl-N'-substituted piperazine sigma receptor ligands on cocaine-induced changes in locomotor activity in mice. Previous reports indicate that N-phenylpropyl-N'-(4-methoxybenzyl)piperazine (Nahas-3h), N-phenylpropyl-N'-(4-methoxyphenethyl)piperazine (YZ-067), and N-phenylpropyl-N'-(3-methoxyphenethyl)piperazine (YZ-185) bind with high affinity (Ki values?1nM) to ?1 sigma receptors. YZ-067 and YZ-185 are known to attenuate cocaine-induced convulsions, while Nahas-3h has not been tested in behavioral studies. Nahas-3h significantly attenuated cocaine-induced hyperactivity. YZ-067 decreased the effect of cocaine in a dose-dependent manner. Interestingly, YZ-185 inhibited cocaine's effect at higher doses, but enhanced cocaine's effect at a low dose. The YZ-185 inhibition of cocaine-induced hyperactivity was not surmounted by increasing the cocaine dose. Overall, this study is consistent with previous work showing the ability of certain sigma receptor ligands to affect cocaine-induced hyperactivity. Further, subtle alterations of ligand structure and the specific dosage levels employed influence the behavioral effects observed, with a 3-methoxy substituent apparently conferring the ability of a ligand to enhance cocaine's locomotor stimulatory effects.

Sage AS; Oelrichs CE; Davis DC; Fan KH; Nahas RI; Lever SZ; Lever JR; Miller DK

2013-09-01

232

Design, synthesis and biological assessment of novel N-substituted 3-(phthalimidin-2-yl)-2,6-dioxopiperidines and 3-substituted 2,6-dioxopiperidines for TNF-? inhibitory activity.  

Science.gov (United States)

Eight novel 2-(2,6-dioxopiperidin-3-yl)phthalimidine EM-12 dithiocarbamates 9 and 10, N-substituted 3-(phthalimidin-2-yl)-2,6-dioxopiperidines 11-14 and 3-substituted 2,6-dioxopiperidines 16 and 18 were synthesized as tumor necrosis factor-? (TNF-?) synthesis inhibitors. Synthesis involved utilization of a novel condensation approach, a one-pot reaction involving addition, iminium rearrangement and elimination, to generate the phthalimidine ring required for the creation of compounds 9-14. Agents were, thereafter, quantitatively assessed for their ability to suppress the synthesis on TNF-? in a lipopolysaccharide (LPS)-challenged mouse macrophage-like cellular screen, utilizing cultured RAW 264.7 cells. Whereas compounds 9, 14 and 16 exhibited potent TNF-? lowering activity, reducing TNF-? by up to 48% at 30 ?M, compounds 12, 17 and 18 presented moderate TNF-? inhibitory action. The TNF-? lowering properties of these analogs proved more potent than that of revlimid (3) and thalidomide (1). In particular, N-dithiophthalimidomethyl-3-(phthalimidin-2-yl)-2,6-dioxopiperidine 14 not only possessed the greatest potency of the analogs to reduce TNF-? synthesis, but achieved this with minor cellular toxicity at 30 ?M. The pharmacological focus of the presented compounds is towards the development of well-tolerated agents to ameliorate the neuroinflammation, that is, commonly associated with neurodegenerative disorders, epitomized by Alzheimer's disease and Parkinson's disease. PMID:21658960

Luo, Weiming; Yu, Qian-sheng; Salcedo, Isidro; Holloway, Harold W; Lahiri, Debomoy K; Brossi, Arnold; Tweedie, David; Greig, Nigel H

2011-05-23

233

Synthesis of aryl aldimines and their activity against fungi of clinical interest.  

UK PubMed Central (United Kingdom)

Aldimines are aldehyde-derived compounds that contain a C=N group. Besides its broad industrial applications, this class of non-naturally occurring compounds are found to possess antibacterial, antifungal, antimalarial, antiproliferative, anti-inflammatory, antiviral, and antipyretic properties. Based on this, six aryl aldimines were synthesized from the condensation of aromatic amines with benzaldehydes. The antifungal activities of synthesized compounds were evaluated against nineteen fungal strains that included Candida and Aspergillus species, Cryptococcus neoformans. The aryl aldimines 2-(benzylideneamino)phenol (3) and 4-(benzylideneamino)phenol (8) were the most active compounds against the fungi studied. Compounds 3 and 8 efficiently inhibited the metabolism of C. neoformans mature biofilm.

da Silva CM; da Silva DL; Martins CV; de Resende MA; Dias ES; Magalhães TF; Rodrigues LP; Sabino AA; Alves RB; de Fátima Â

2011-11-01

234

Synthesis and pharmacological evaluation of (6-substituted 4-Oxo-4 H -chromene-3 yl) methyl N-substituted aminoacetates  

Directory of Open Access Journals (Sweden)

Full Text Available A series of the title compounds were synthesized and characterized by spectral data. All the compounds were evaluated for in vitro antihistaminic activity by inhibition of isotonic contractions induced by histamine on isolated guinea pig ileum and the compound 6-k showed significant activity. A few compounds have also been screened for in vivo bronchodilatory activity. These compounds exhibited significant protection against histamine-induced convulsions in guinea pig at the dose of 50 µmol.

Gajbhiye Asmita; Mallareddy V; Achaiah G

2008-01-01

235

Nickel-catalysed aromatic Finkelstein reaction of aryl and heteroaryl bromides.  

UK PubMed Central (United Kingdom)

A fast and efficient nickel-catalysed iodination reaction of aryl and heteroaryl bromides has been developed. The transformation was found to be general for a wide range of substrates and was used for the synthesis of iodo-PK11195, an imaging agent of Alzheimer's disease and iniparib, a compound used in the treatment of breast cancer.

Cant AA; Bhalla R; Pimlott SL; Sutherland A

2012-04-01

236

N-Aryl-benzimidazolones as novel small molecule HSP90 inhibitors  

Energy Technology Data Exchange (ETDEWEB)

We describe the development of a novel series of N-aryl-benzimidazolone HSP90 inhibitors (9) targeting the N-terminal ATP-ase site. SAR development was influenced by structure-based design based around X-ray structures of ligand bound HSP90 complexes. Lead compounds exhibited high binding affinities, ATP-ase inhibition and cellular client protein degradation.

Bruncko, Milan; Tahir, Stephen K.; Song, Xiaohong; Chen, Jun; Ding, Hong; Huth, Jeffrey R.; Jin, Sha; Judge, Russell A.; Madar, David J.; Park, Chang H.; Park, Cheol-Min; Petros, Andrew M.; Tse, Christin; Rosenberg, Saul H.; Elmore, Steven W. (Abbott)

2012-03-16

237

Efficient synthesis of oxygenated terphenyls and other oligomers: sequential arylation reactions through phenol oxidation-rearomatization.  

UK PubMed Central (United Kingdom)

One by one: starting from simple phenols, a diverse series of oxygenated terphenyl compounds can be prepared in a concise and practical manner using sequential arylation reactions involving phenol oxidation/rearomatization and quinone monoacetal intermediates. Many of the terphenyl products can be used for preparing well-defined oligomers and, furthermore, contain valuable functional groups that can be transformed for further diversification.

Dohi T; Kamitanaka T; Watanabe S; Hu Y; Washimi N; Kita Y

2012-10-01

238

Dearomatizing Conjugate Addition to Quinolinyl Amidines for the Synthesis of Dehaloperophoramidine through Tandem Arylation and Allylation.  

UK PubMed Central (United Kingdom)

Dehaloperophoramidine, the dehalogenated analogue of the marine hexacyclic alkaloid perophoramidine was synthesized. The intramolecular nucleophilic dearomatizing arylation of aminoquinoline initiated by a lithium-iodine exchange and the subsequent direct allylation of the resultant azaenolate afforded a pentacyclic bisamidine compound bearing two contiguous all-carbon quaternary centers in good yield with excellent diastereoselectivity.

Ishida T; Ikota H; Kurahashi K; Tsukano C; Takemoto Y

2013-08-01

239

Selective electrochemical oxidation of organic compounds  

Energy Technology Data Exchange (ETDEWEB)

The present invention relates to a method and electrochemical cell useful for the selective electrochemical oxidation of aryl-compounds including aromatic and polynuclear aromatic hydrocarbons such as benzene, naphthalene and anthracene or their derivatives such as phenols and naphthols. The anodic electrode of the cell includes a first foraminous or porous layer of a hydrophobic material; a second foraminous or porous layer which includes an oxidation catalyst; and an electrical current collector in contact with the second layer. As a result of the special chemical properties and porosity of the first and second layers of the anode, and because of careful control of the pressure differential between the electrolyte solution and the aryl-compound, an active interface is formed by the electrolyt solution and aryl-compound between the first and second layers or in the second layer of the anode thereby providing for very selective controlled oxidation of the aryl-compound with excellent current efficiencies.

Noding, S. A.

1985-09-24

240

Stereoselective synthesis of spiropiperidines as BACE-1 aspartyl protease inhibitors via late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore.  

UK PubMed Central (United Kingdom)

A stereoselective synthesis of spiropiperidine compounds, exemplified by compound 1, was developed, which was based upon the late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore. Previously, compound 1 was prepared in low overall yield from piperidinone 2 via the Strecker reaction. A new route was developed, which employed the stereospecific Corey-Link reaction of an enantiomerically pure trichloromethylcarbinol to give a template compound amenable to late stage N-arylation.

Lee CW; Lira R; Dutra J; Ogilvie K; O'Neill BT; Brodney M; Helal C; Young J; Lachapelle E; Sakya S; Murray JC

2013-03-01

 
 
 
 
241

The aryl hydrocarbon receptor and food allergy.  

UK PubMed Central (United Kingdom)

The immune system is important for protection against pathogens and malignant cells. However, malfunction of the immune system can also result in detrimental auto-immune diseases, inflammatory diseases, cancers and allergies. The aryl hydrocarbon receptor (AhR), present in numerous tissues and cell subsets, including cells of the immune system, plays an important role in the functioning of the immune system. Activation of the AhR is for example associated with various effects on dendritic cells (DCs), regulatory T cells and the Th1/Th2 cell balance. These cells play a major role in the development of food allergy. Food allergy is an increasing health problem in both humans and animals. Despite the knowledge in risk factors and cellular mechanisms for food allergy, no approved treatments are available yet. Recently, it has been shown that activation of the AhR by dioxin-like compounds suppresses allergic sensitization by suppressing the absolute number of precursor and effector T cells, by preserving CD4(+)CD25(+)Foxp3(+) Treg cells and by affecting DCs and their interaction with effector T cells. Future research should elucidate whether and how AhR activation can be used to interfere in food allergic responses in humans and in animals. This may lead to new prevention strategies and therapeutic possibilities for food allergy.

Schulz VJ; Smit JJ; Pieters RH

2013-06-01

242

Radioiodination of aryl-alkyl cyclic sulfates.  

UK PubMed Central (United Kingdom)

Among the currently available positron emitters suitable for Positron Emission Tomography (PET), (124)I has the longest physical half-life (4.2 days). The long half-life and well-investigated behavior of iodine in vivo makes (124)I very attractive for pharmacological studies. In this communication, we describe a simple yet effective method for the synthesis of novel (124)I labeled compounds intended for PET imaging of arylsulfatase activity in vivo. Arylsulfatases have important biological functions, and genetic deficiencies of such functions require pharmacological replacement, the efficacy of which must be properly and non-invasively evaluated. These enzymes, even though their natural substrates are mostly of aliphatic nature, hydrolyze phenolic sulfates to phenol and sulfuric acid. The availability of [(124)I]iodinated substrates is expected to provide a PET-based method for measuring their activity in vivo. The currently available methods of synthesis of iodinated arylsulfates usually require either introducing of a protected sulfate ester early in the synthesis or introduction of sulfate group at the end of synthesis in a separate step. The described method gives the desired product in one step from an aryl-alkyl cyclic sulfate. When treated with iodide, the source cyclic sulfate opens with substitution of iodide at the alkyl center and gives the desired arylsulfate monoester.

Mushti C; Papisov MI

2012-01-01

243

Synthesis and antifungal activity of novel (1-aryl-2-heterocyclyl)ethylideneaminooxymethyl-substituted dioxolanes  

Energy Technology Data Exchange (ETDEWEB)

A novel series of (1-aryl-2-heterocyclyl)ethylideneaminooxymethyl -substituted dioxolanes IIIa-n were synthesized by condensation of substituted 1,3-dioxolan-4-ylmethyl p-toluenesulfonates 4 with 1-(hydroxyimino)-1-aryl-2-heterocyclylethanes 5. Compounds IIIa-n were found to have effective in vitro antifungal activity when evaluated against the pathogenic fungi Candida albicans, Aspergillus flavus and Fusarium solani with MIC (minimum inhibitory concentration) values of 10 {mu}g-ml{sup -1} for IIIa-I and 5 {mu}g-ml{sup -1} for IIIm,n. (authors). 24 refs., 4 figs., 5 tabs.

Baji, H.; Flammang, M.; Kimny, T.; Gasquez, F.; Compagnon, P.L.; Delcourt, A. [Dijon Univ., 21 (France)

1995-12-31

244

Synthesis and antibacterial activity of some novel 2-Aroylimino-3-aryl-thiazolidin-4-ones  

International Nuclear Information System (INIS)

An efficient, regioselective synthesis of some 2-aroylimino-3-aryl-thiazolidin-4-ones (2aj) involving base-catalyzed cyclization of 1-aroyl-3-aryl thioureas with chloroacetyl chloride in dioxane is reported. The structures were confirmed by spectroscopic data, elemental analyses and in one case (2j) by single crystal X-ray diffraction data. Compounds (2a-j) were assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria and were found to exhibit promising activity towards the tested microorganisms, comparable to and in some cases better than those of the standard drugs. (author)

2007-01-01

245

Synthesis and anticancer activity of new 2-aryl-4h-3,1-benzothiazines.  

UK PubMed Central (United Kingdom)

New compounds of 2-aryl-4H-3,1-benzothiazine set were synthesized and tested for their antiproliferative activity as part of our research in the antitumor field. The title compounds were obtained by the reaction of aryl-modified sulfinylbis((2,4-dihydroxyphenyl)methanethione) with 2-aminobenzyl alcohols. The reaction proceeded through thiobenzanilide intermediates, which were converted to the 4H-3,1-benzothiazine fused ring by an endocyclization process. The structures of compounds were identified from elemental, IR, (1) H-NMR, (13) C-NMR, and MS spectra analyses. The cytotoxicity in vitro against four human cancer cell lines was determined. The antiproliferative properties of some compounds were more beneficial than cisplatin studied comparatively.

Niewiadomy A; Matysiak J; Karpi?ska MM

2011-04-01

246

Synthesis and anticancer activity of new 2-aryl-4h-3,1-benzothiazines.  

Science.gov (United States)

New compounds of 2-aryl-4H-3,1-benzothiazine set were synthesized and tested for their antiproliferative activity as part of our research in the antitumor field. The title compounds were obtained by the reaction of aryl-modified sulfinylbis((2,4-dihydroxyphenyl)methanethione) with 2-aminobenzyl alcohols. The reaction proceeded through thiobenzanilide intermediates, which were converted to the 4H-3,1-benzothiazine fused ring by an endocyclization process. The structures of compounds were identified from elemental, IR, (1) H-NMR, (13) C-NMR, and MS spectra analyses. The cytotoxicity in vitro against four human cancer cell lines was determined. The antiproliferative properties of some compounds were more beneficial than cisplatin studied comparatively. PMID:21469171

Niewiadomy, Andrzej; Matysiak, Joanna; Karpi?ska, Monika M

2011-01-14

247

Unusual Inner C-Alkylation of 2-N-Substituted N-Confused Porphyrin Cobalt Complexes in Toluene and p-Xylene.  

UK PubMed Central (United Kingdom)

The inner C-benzyl- and C-p-xylyl-substituted cobalt(II) complexes of a 2-N-substituted N-confused porphyrin were synthesized from the reaction of 2-NCH2COOCH2C6H5NCTPPH (1) and CoCl2·6H2O in toluene (or p-xylene), and the structures were revealed by single-crystal X-ray analysis.

Wang YC; Chen JH; Wang SS; Tung JY

2013-09-01

248

Synthesis and antihyperglycemic evaluation of new 2,4-thiazolidinediones having biodynamic aryl sulfonylurea moieties.  

UK PubMed Central (United Kingdom)

New 2,4-thiazolidinediones with aryl sulfonylurea moieties have been synthesized by condensing various substituted sulfonamides and 5-(isocyanatomethyl) thiazolidino-2,4-dione. The isocyanomethyl thiazolidinedione was obtained by using the Curtius rearrangement, starting from known 2,4-dioxo-5-thiazolidineacetic acid. The newly synthesized compounds have been evaluated for the antihyperglycemic activity in normal rats model and among these compounds showed significant antihyperglycemic activity in sucrose loaded rat model.

Jawale DV; Pratap UR; Rahuja N; Srivastava AK; Mane RA

2012-01-01

249

Synthesis and antihyperglycemic evaluation of new 2,4-thiazolidinediones having biodynamic aryl sulfonylurea moieties.  

Science.gov (United States)

New 2,4-thiazolidinediones with aryl sulfonylurea moieties have been synthesized by condensing various substituted sulfonamides and 5-(isocyanatomethyl) thiazolidino-2,4-dione. The isocyanomethyl thiazolidinedione was obtained by using the Curtius rearrangement, starting from known 2,4-dioxo-5-thiazolidineacetic acid. The newly synthesized compounds have been evaluated for the antihyperglycemic activity in normal rats model and among these compounds showed significant antihyperglycemic activity in sucrose loaded rat model. PMID:22123321

Jawale, Dhanaji V; Pratap, Umesh R; Rahuja, Neha; Srivastava, Arvind K; Mane, Ramrao A

2011-11-09

250

Synthesis and antileishmanial activity of new 1-Aryl-1H-Pyrazole-4- carboximidamides derivatives  

Energy Technology Data Exchange (ETDEWEB)

Chemotherapy for leishmaniasis, diseases caused by protozoa of the genus Leishmania, remains inefficient in several treatments. So there is a need to search for new drugs. In this work, we have synthesized 1-aryl-1H-pyrazole-4-carboximidamides derivatives and evaluated antileishmanial activities in vitro, as well as cytotoxic effects. Structure-activity relationship (SAR) studies were carried out with all the compounds of the series. Compound 2 showed an activity profile that can be improved through medicinal chemistry strategies. (author)

Santos, Mauricio S. dos; Gomes, Adriana O.; Bernardino, Alice M.R.; Souza, Marcos C. de, E-mail: alicerolim@globo.co [Universidade Federal Fluminense (UFF), Niteroi, RJ (Brazil). Programa de Pos-Graduacao em Quimica Organica; Khan, Misbahul A. [The Islamia University of Bahawalpur (Pakistan). Chemistry Dept.; Brito, Monique A. de [Universidade Federal Fluminense (UFF), Niteroi, RJ (Brazil). Fac. de Farmacia. Lab. de Quimica Medicinal Computacional; Castro, Helena C.; Abreu, Paula A. [Universidade Federal Fluminense (LABioMol/GCM/UFF), Niteroi, RJ (Brazil). Inst. de Biologia. Lab. de Antibioticos, Bioquimica e Modelagem Molecular; Rodrigues, Carlos R. [Universidade Federal do Rio de Janeiro (ModMol/UFRJ), RJ (Brazil). Fac. de Farmacia. Lab. de Modelagem Molecular e QSAR; Leo, Rosa M.M. de; Leon, Leonor L.; Canto-Cavalheiro, Marilene M. [Fundacao Oswaldo Cruz (IOC/FIOCRUZ), Rio de Janeiro, RJ (Brazil). Instituto Oswaldo Cruz. Lab. de Bioquimica de Tripanosomatideos

2011-07-01

251

Identification of 2-amino-5-aryl-pyrazines as inhibitors of human lactate dehydrogenase.  

UK PubMed Central (United Kingdom)

A 2-amino-5-aryl-pyrazine was identified as an inhibitor of human lactate dehydrogenase A (LDHA) via a biochemical screening campaign. Biochemical and biophysical experiments demonstrated that the compound specifically interacted with human LDHA. Structural variation of the screening hit resulted in improvements in LDHA biochemical inhibition and pharmacokinetic properties. A crystal structure of an improved compound bound to human LDHA was also obtained and it explained many of the observed structure-activity relationships.

Fauber BP; Dragovich PS; Chen J; Corson LB; Ding CZ; Eigenbrot C; Giannetti AM; Hunsaker T; Labadie S; Liu Y; Liu Y; Malek S; Peterson D; Pitts K; Sideris S; Ultsch M; Vanderporten E; Wang J; Wei B; Yen I; Yue Q

2013-10-01

252

QUINOLIN-2-ONE COMPOUNDS  

UK PubMed Central (United Kingdom)

A compound of structural formula [1]: in which: A represents a direct bond, an optionally substituted alkylene or alkenylene group, or a group of formula Z-(optionally substituted)alkylene B represents a direct bond, an optionally substituted alkylene or alkenylene group, or a group of formula Z-(optionally substituted)alkylene or (optionally substituted)alkylene-Z Z represents an oxygen atom, an NH or N-alkyl group, a group of formula S(O)n, in which n = 0 to 2, or a group of formula -O-SO2- X represents a carboxylic acid, tetrazole, 3-hydroxyisoxazole, hydroxamic acid, phosphinate, phosphonate, phosphonamide, sulfonic acid or a group of formula C(=O)NHSO2W or SO2NHC(=O)W W represents an optionally substituted aryl or heteroaryl group or an optionally substituted alkyl group Y represents an optionally substituted aryl or heteroaryl group, or an optionally substituted aryl-fused-heterocycloalkyl, heteroaryl-fused-cycloalkyl, heteroaryl-fused-heterocycloalkyl, aryl-fused-cycloalkyl or cycloalkyl group Ra, Rb and Rc independently represent hydrogen, acyl, alkoxy, alkylsulphinyl, alkylsulphonyl, alkylthio, -NH2, aminoalkyl, hydroxyalkyl, arylalkyl, cyano, dialkylamino, halo, haloalkoxy, haloalkyl, alkyl, alkenyl, -OH, -CHO, -NO2, aryl (optionally substituted with alkoxy, haloalkoxy, halogen, alkyl or haloalkyl), heteroaryl (optionally substituted with alkoxy, haloalkoxy, halogen, alkyl or haloalkyl), heterocycloalkyl, aminoacyl, aminosulphonyl, acylamino, sulphonylamino, heteroarylalkyl, cyclic amine, aryloxy, heteroaryloxy, arylalkyloxy or heteroarylalkyloxy

HYND GEORGE; MONTANA JOHN GARY; FINCH HARRY; CRAMP MICHAEL COLIN; WARD STUART

253

?-Arylation, ?-Arylative Esterification, or Acylation: A Stoichiometry-Dependent Trichotomy in the Pd-Catalyzed Cross-Coupling between Aldehydes and Aryl Bromides.  

UK PubMed Central (United Kingdom)

Three's company: The selective ?-arylation and ?-arylative esterification of linear and branched aldehydes is reported for a variety of bromoarenes. The acylation of aryl bromides can be achieved with linear aldehydes. All these transformations were performed with a single [(N-heterocyclic carbene)Pd] catalyst through adjustment of the stoichiometry of the reagents and the appropriate base.

Nareddy P; Mazet C

2013-08-01

254

NOVEL ORGANIC GERMANIUM COMPOUNDS  

UK PubMed Central (United Kingdom)

The present invention relates to organic germanium compounds represented by the following Formula 1, or salts thereof. [Formula 1] In said Formula 1, R1, R2 and R3 are the same or different from one another, and are independently a C1-C6 linear or branched alkyl group, a C2-C6 linear or branched alkenyl group, a C2-C6 linear or branched alkynyl group, an aryl group, an aryl group substituted with a C1-C6 linear or branched alkyl group, an aryl group substituted with a C2-C6 linear or branched alkenyl group, or an aryl group substituted with a C2-C6 linear or branched alkynyl group R4 is a monosaccharide, an alcohol, L-ascorbic acid, L-ascorbic acid derivatives having a protected hydroxyl group at the carbon atom of the two position in a furan ring of L-ascorbic acid, or amine derivative thereof m is an integer of 0-10 X is CO or CH2 and Ge is germanium. The novel organic germanium compounds of the present invention are remarkably improved in water solubility, thereby enabling easy in vivo absorption, is free from the accumulation in tissue, thereby showing no toxicity in the body, and can sufficiently show the original effect of germanium. In addition, a compound combined with L-ascorbic acid shows a strong antioxidizing activity.

HAM SEUNG WOOK

255

Pd(OAc)2/o-chloranil/M(OTf)n: a catalyst for the direct C-H arylation of polycyclic aromatic hydrocarbons with boryl-, silyl-, and unfunctionalized arenes.  

UK PubMed Central (United Kingdom)

Pd(OAc)(2)/o-chloranil/M(OTf)(n) can effectively promote the C-H arylation of fluoranthene with arylboron compounds or arylsilanes. The reaction takes place with high regioselectivity at the C3 position of fluoranthene. Moreover, the new catalytic system allows the use of unfunctionalized arenes as coupling partners in the arylation of polycyclic aromatic hydrocarbons.

Kawasumi K; Mochida K; Kajino T; Segawa Y; Itami K

2012-01-01

256

Free-Amine Directed Arylation of Biaryl-2-amines with Aryl Iodides by Palladium Catalysis.  

UK PubMed Central (United Kingdom)

A new palladium-catalyzed free-amine directed arylation of C(sp(2))-H bonds in the presence of AgOAc and TFA is described. Biaryl-2-amines react with various aryl iodides to give the corresponding mono- or diarylated products with exclusive regioselectivity.

Liang Z; Feng R; Yin H; Zhang Y

2013-09-01

257

Free-Amine Directed Arylation of Biaryl-2-amines with Aryl Iodides by Palladium Catalysis.  

Science.gov (United States)

A new palladium-catalyzed free-amine directed arylation of C(sp(2))-H bonds in the presence of AgOAc and TFA is described. Biaryl-2-amines react with various aryl iodides to give the corresponding mono- or diarylated products with exclusive regioselectivity. PMID:23981087

Liang, Zunjun; Feng, Ruokun; Yin, Hong; Zhang, Yuhong

2013-08-28

258

Rhodium-catalyzed oxidative C-H arylation of 2-arylpyridine derivatives via decarbonylation of aromatic aldehydes.  

UK PubMed Central (United Kingdom)

A new concept for aryl-aryl coupling that involves oxidative decarbonylative coupling of aryl C-H bonds and readily available aldehydes has been developed, achieving the aryl-aryl union with complete control of reaction sites.

Shuai Q; Yang L; Guo X; Baslé O; Li CJ

2010-09-01

259

Structural and functional models for the dinuclear copper active site in catechol oxidases. Synthesis, X-ray crystal structures, magnetic and spectroscopic properties of mu-methoxo-bridged dinuclear copper(II) complexes with N-substituted sulfonamide ligands.  

UK PubMed Central (United Kingdom)

Two new mu-methoxo-bridged dinuclear copper(II) complexes with a N-substituted sulfonamide, [Cu(mu-OMe)(L)(NH(3))](2) (1) and [Cu(mu-OMe)(L)(DMSO)](2) (2) [HL, N-2-(4-methylbenzothiazole)benzenesulfonamide], have been prepared and characterized by single-crystal X-ray difraction analyses. Compound 1 crystallizes in the monoclinic space group C(2)/c with a=22.0678(18), b=7.9134(7), c=21.1186(18)A, beta=113.788(4) degrees and Z=8. Compound 2 crystallizes in the monoclinic space group C(2)/c with a=18.0900(10), b=9.5720(10), c=24.2620(10) A, beta=98.7120(10) degrees and Z=8. In both complexes the copper atoms have square-planar environments bridged by two oxygen atoms from methoxide groups. Magnetic susceptibility measurements indicate a very strong antiferromagnetic coupling between the copper(II) ions in both complexes (2J<-1000 cm(-1)). Electronic Paramagnetic Resonance (EPR) spectra of the two complexes both in solid and in solution are silent. 13C NMR spectra of the complexes in solid state have been studied. The complexes have been evaluated as model systems for the catechol oxidase enzyme using 3,5-di-tert-butylcatechol as the test substrate. Complex 2 is slightly more active than complex 1.

González-Alvarez M; Alzuet G; Borrás J; García-Granda S; Montejo-Bernardo JM

2003-09-01

260

4- not (Aryl)(aryloxy)methyl piperidine derivatives and their use as serotonin and/or noradrenaline reuptake inhibitors  

UK PubMed Central (United Kingdom)

New 4-substituted piperidines of general formula (I) are described in which groups R1 and R2 are non-substituted aryl radicals or aryl radicals mono- or poly-substituted with halogen (fluorine, chlorine, bromine, iodine), alkyl, alkoxy, cyano, trifluoromethoxy, trifluoromethyl, benzoyl, phenyl, nitro, amino, aminoalkyl, aminoaryl and carbonylamino. These compounds, and their pharmaceutically acceptable salts, inhibit serotonin and/or noradrenaline reuptake, and are useful as antidepressants. Other potential therapeutic applications of these compounds are treatment of nervous bulimia, obsessive-compulsive disorders, alcohol addiction, anxiety, panic, pain, pre-menstrual syndrome and social phobia, as well as migraine prophylaxis.

ORJALES VENERO AURELIO; TOLEDO AVELLO ANTONIO; PUMAR DURAN CARMEN

 
 
 
 
261

Structural insights on the molecular recognition patterns between N(6)-substituted adenines and N-(aryl-methyl)iminodiacetate copper(II) chelates.  

Science.gov (United States)

For a better understanding of the metal binding pattern of N(6)-substituted adenines, six novel ternary Cu(II) complexes have been structurally characterized by single crystal X-ray diffraction: [Cu(NBzIDA)(HCy5ade)(H2O)]·H2O (1), [Cu(NBzIDA)(HCy6ade)(H2O)]·H2O (2), [Cu(FurIDA)(HCy6ade)(H2O)]·H2O (3), [Cu(MEBIDA)(HBAP)(H2O)]·H2O (4), [Cu(FurIDA)(HBAP)]n (5) and {[Cu(NBzIDA)(HdimAP)]·H2O}n (6). In these compounds NBzIDA, FurIDA and MEBIDA are N-substituted iminodiacetates with a non-coordinating aryl-methyl pendant arm (benzyl in NBzIDA, p-tolyl in MEBIDA and furfuryl in FurIDA) whereas HBAP, HCy5ade, HCy6ade and HdimAP are N(6)-substituted adenine derivatives with a N-benzyl, N-cyclopentyl, N-cyclohexyl or two N-methyl groups, respectively. Regardless of the molecular (1-4) or polymeric (5-6) nature of the studied compounds, the Cu(II) centre exhibits a type 4+1 coordination where the tridentate IDA-like chelators adopt a mer-conformation. In 1-5 the N(6)-R-adenines use their most stable tautomer H(N9)adenine-like, and molecular recognition consists of the cooperation of the CuN3(purine) bond and the intra-molecular interligand N9H···O(coordinated carboxy) interaction. In contrast, N(6),N(6)-dimethyl-adenine shows the rare tautomer H(N3)dimAP in 6, so that the molecular recognition with the Cu(NBzIDA) chelate consist of the CuN9 bond and the N3H···O intra-molecular interligand interaction. Contrastingly to the cytokinin activity found in the free ligands HBAP (natural cytokinin), HCy5ade and HCy6ade, the corresponding Cu(II) ternary complexes did not show any activity. PMID:23490423

Domínguez-Martín, Alicia; García-Raso, Angel; Cabot, Catalina; Choquesillo-Lazarte, Duane; Pérez-Toro, Inmaculada; Matilla-Hernández, Antonio; Castiñeiras, Alfonso; Niclós-Gutiérrez, Juan

2013-02-15

262

Synthesis and antiplatelet evaluation of novel aryl-sulfonamide derivatives, from natural safrole.  

UK PubMed Central (United Kingdom)

In the scope of a research program aiming at the synthesis and pharmacological evaluation of novel possible antiplatelet prototype compounds, exploring bioisosterism principles for molecular design, we describe in this paper the synthesis of new aryl-sulfonamides derivatives, structurally similar to known thromboxane A2 receptor antagonists. The synthetic route used to access the new compounds described herein starts from safrole, an abundant Brazilian natural product, which occurs in Sassafras oil (Ocotea pretiosa). The results from preliminary evaluation of these novel aryl-sulfonamide compounds by the platelet aggregation inhibitory test, using rabbit PRP, induced by ADP, collagen, arachidonic acid, and U46619, identified the N-[2-(4-carboxymethoxyphenyl)ethyl]-6-methyl-3,4-methylenedioxyphe nyl- sulfonamido derivative as the most active among them, presenting in IC50 value for the U-46619-induced platelet aggregation in rabbit platelet-rich plasma: 329 microM.

Lima LM; Ormelli CB; Brito FF; Miranda AL; Fraga CA; Barreiro EJ

1999-06-01

263

Synthesis and antiplatelet evaluation of novel aryl-sulfonamide derivatives, from natural safrole.  

Science.gov (United States)

In the scope of a research program aiming at the synthesis and pharmacological evaluation of novel possible antiplatelet prototype compounds, exploring bioisosterism principles for molecular design, we describe in this paper the synthesis of new aryl-sulfonamides derivatives, structurally similar to known thromboxane A2 receptor antagonists. The synthetic route used to access the new compounds described herein starts from safrole, an abundant Brazilian natural product, which occurs in Sassafras oil (Ocotea pretiosa). The results from preliminary evaluation of these novel aryl-sulfonamide compounds by the platelet aggregation inhibitory test, using rabbit PRP, induced by ADP, collagen, arachidonic acid, and U46619, identified the N-[2-(4-carboxymethoxyphenyl)ethyl]-6-methyl-3,4-methylenedioxyphe nyl- sulfonamido derivative as the most active among them, presenting in IC50 value for the U-46619-induced platelet aggregation in rabbit platelet-rich plasma: 329 microM. PMID:10443173

Lima, L M; Ormelli, C B; Brito, F F; Miranda, A L; Fraga, C A; Barreiro, E J

1999-06-01

264

Research on antibacterial and antifungal agents. XIII. Synthesis and antimicrobial activity of 1-arylmethyl-4-aryl-1H-pyrrole-3-carboxylic acids.  

UK PubMed Central (United Kingdom)

Several 1-arylmethyl-4-aryl-1H-pyrrole-3-carboxylic acid derivatives have been synthetized and tested as antifungal and antibacterial agents. Reaction between tosylmethylisocyanide (TosMIC) and beta-arylacrylic esters under basic conditions furnished 4-aryl-1H-pyrrole-3-carboxylic esters, which were then benzylated at 1 position. Alkaline hydrolysis of ethyl 1-arylmethyl-4-aryl-1H-pyrrole-3-carboxylates afforded the title compounds. All tested derivatives were found to be inactive as antifungal agents. Some of them showed appreciable antibacterial activities against Staphylococcus spp.

Massa S; Di Santo R; Mai A; Botta M; Artico M; Panico S; Simonetti G

1990-07-01

265

Research on antibacterial and antifungal agents. XIII. Synthesis and antimicrobial activity of 1-arylmethyl-4-aryl-1H-pyrrole-3-carboxylic acids.  

Science.gov (United States)

Several 1-arylmethyl-4-aryl-1H-pyrrole-3-carboxylic acid derivatives have been synthetized and tested as antifungal and antibacterial agents. Reaction between tosylmethylisocyanide (TosMIC) and beta-arylacrylic esters under basic conditions furnished 4-aryl-1H-pyrrole-3-carboxylic esters, which were then benzylated at 1 position. Alkaline hydrolysis of ethyl 1-arylmethyl-4-aryl-1H-pyrrole-3-carboxylates afforded the title compounds. All tested derivatives were found to be inactive as antifungal agents. Some of them showed appreciable antibacterial activities against Staphylococcus spp. PMID:2282118

Massa, S; Di Santo, R; Mai, A; Botta, M; Artico, M; Panico, S; Simonetti, G

1990-07-01

266

Selective arylation at the vinylic site of cyclic olefins.  

UK PubMed Central (United Kingdom)

Cyclic olefins usually give Heck products having an aryl ring residing at the allylic or homoallylic position. We describe herein a new method that allows arylation at the vinylic position of various cyclic olefins.

Wu X; Zhou JS

2013-05-01

267

GREEN SYNTHESIS OF ARYL ALDIMINES USING ETHYL LACTATE  

UK PubMed Central (United Kingdom)

The present invention relates to a method for preparing aryl aldimines. In particular, the present invention relates to methods of preparing aryl aldimines that uses environmentally friendly solvent systems.

BENNETT JACQUELINE S

268

Meta-arylation of calixarenes using organomercurial chemistry.  

UK PubMed Central (United Kingdom)

A direct mercuration reaction combined with a subsequent Pd-catalyzed arylation was used to introduce the aryl moiety into the meta position of the calix[4]arene skeleton. The application of organomercurial intermediates thus allows the straightforward formation of meta-aryl-substituted derivatives representing a unique substitution pattern in calixarene chemistry.

Slavík P; Flídrová K; Dvo?áková H; Eigner V; Lhoták P

2013-09-01

269

Silver-Mediated Trifluoromethoxylation of Aryl Stannanes and Arylboronic Acids  

Digital Repository Infrastructure Vision for European Research (DRIVER)

A silver-mediated cross-coupling of trifluoromethoxide with aryl stannanes and arylboronic acids to give aryl trifluoromethyl ethers is reported. This is the first report of a transition-metal-mediated \\(C_{aryl}–OCF_3\\) bond formation. , Chemistry and Chemical Biology

Huang, Chenghong; Liang, Theresa; Harada, Shinji; Lee, Eunsung; Ritter, Tobias

270

Meta-arylation of calixarenes using organomercurial chemistry.  

Science.gov (United States)

A direct mercuration reaction combined with a subsequent Pd-catalyzed arylation was used to introduce the aryl moiety into the meta position of the calix[4]arene skeleton. The application of organomercurial intermediates thus allows the straightforward formation of meta-aryl-substituted derivatives representing a unique substitution pattern in calixarene chemistry. PMID:23863891

Slavík, Petr; Flídrová, Karolína; Dvo?áková, Hana; Eigner, Václav; Lhoták, Pavel

2013-07-31

271

Design, Synthesis and Antifibrotic Activities of Carbohydrate- Modified 1-(Substituted aryl)-5-trifluoromethyl-2(1H) Pyridones  

Directory of Open Access Journals (Sweden)

Full Text Available Pirfenidone, a pyridone compound, is an effective and novel antifibrotic agent. In this article, we describe the design, synthesis and activity evaluation of novel antifibrotic agents, 1-(substituted aryl)-5-trifluoromethyl-2(1H) pyridones modified with carbohydrate. Most of the title compounds exhibited comparable or better inhibitory activity than fluorofenidone. Notably, compound 19a demonstrated the highest cell-based inhibitory activity against NIH 3T3 (IC50 = 0.17 mM).

Qinghua Lou; Xiangbao Meng; Zhiqi Lao; Lingling Xuan; Jinye Bai; Qi Hou; Gaoyun Hu; Renna Luo; Lijian Tao; Zhongjun Li

2012-01-01

272

Synthesis and cytotoxic activity of some 2-amino-4-aryl-3-cyano-7-(dimethylamino)-4H-chromenes.  

Science.gov (United States)

A series of 2-amino-4-aryl-3-cyano-7- (dimethylamino)-4H-chromenes was synthesized by condensation of 3- (dimethylamino) phenol, an aromatic aldehyde and malonitrile in ethanol containing piperidine. The assignments of the structure of all synthesized compounds were based on spectral data (IR, Mass and(1)H NMR). The cytotoxic activities of the synthesized compounds against six human tumor cell lines were determined by MTT assay. Several compounds showed significant cytotoxic activity. PMID:21589763

Vosooghi, M; Rajabalian, S; Sorkhi, M; Badinloo, M; Nakhjiri, M; Negahbani, A S; Asadipour, A; Mahdavi, M; Shafiee, A; Foroumadi, A

2010-01-01

273

Synthesis and cytotoxic activity of some 2-amino-4-aryl-3-cyano-7-(dimethylamino)-4H-chromenes.  

UK PubMed Central (United Kingdom)

A series of 2-amino-4-aryl-3-cyano-7- (dimethylamino)-4H-chromenes was synthesized by condensation of 3- (dimethylamino) phenol, an aromatic aldehyde and malonitrile in ethanol containing piperidine. The assignments of the structure of all synthesized compounds were based on spectral data (IR, Mass and(1)H NMR). The cytotoxic activities of the synthesized compounds against six human tumor cell lines were determined by MTT assay. Several compounds showed significant cytotoxic activity.

Vosooghi M; Rajabalian S; Sorkhi M; Badinloo M; Nakhjiri M; Negahbani AS; Asadipour A; Mahdavi M; Shafiee A; Foroumadi A

2010-01-01

274

SAR of new 1-substitutedmethyl-4-[5-(N-methyl-N-propylamino)pentyloxy]piperidines and selected 1-[(N-substituted-N-methyl)-3-propyloxy]-5-(N-methyl-N-propyl)pentane- diamines as H3 -antagonists.  

UK PubMed Central (United Kingdom)

Novel, potent non-imidazole histamine H3 receptor antagonists have been prepared and in vitro tested as H3 -receptor antagonists (the electrically evoked contraction of the guinea-pig jejunum). The present compounds contain a 4-hydroxypiperidine core, which behaves as a conformationally restricted version of the 3-amino-1-propanol moiety common to the many previously described non-imidazole H3 ligands. Detailed structure-activity studies revealed that 1-(2-benzofuranylmethyl)- 5c (pA2 =8.47 ± 0.05) and 1-(3-benzofuranylmethyl)-4-[5-(N-methyl-N-propyl)pentyloxy]piperidine 5d (pA2 =8.15 ± 0.07), exhibit high potency for the H3 histamine receptor. In addition, the potency of selected 1-[(N-substituted-N-methyl)-3-propyloxy]-5-(N-methyl-N-propyl)pentanediamines as antagonist of the H3 histamine receptor was also evaluated. Replacement of the 4-hydroxypiperidine of the leads 7 and 5c by a highly flexible 3-(methylamino)propyloxy chain yields compounds 6a (pA2 =8.02) and 6b (pA2 =6.23) with higher and lower potency than their piperidine analogues (7, pA2 =7.79; 5c, pA2 =8.47), respectively. The histaminergic H1 antagonism of selected compounds 5c, 5d and 6a has been established on the isolated guinea-pig ileum by conventional methods; the pA2 values have compared with the potency of pyrilamine. None of them showed any H1 -antagonistic activity (pA2 <4; for pyrilamine pA2 =8.5) This article is protected by copyright. All rights reserved.

Mas?owska-Lipowicz I; Walczy?ski K

2013-08-01

275

Azoles and azines. 62. Structure of 2-aryl-1,3-oxazine-4,6-diones  

Energy Technology Data Exchange (ETDEWEB)

/sup 1/H, /sup 13/C NMR, IR, and UV spectra have been studied for solutions of a number of potentially tautomeric 2-aryl-1,3-oxazine-4,6-diones and their 5-methyl substituted analogs with variation of substituent at the para position of the benzene ring, as well as compounds with a fixed structure that simulates possible tautomeric forms. The data have been compared with the results of quantum chemical calculations carried out in SSO MO LCAO approximation by the CNO, CNDO/2, and MPNDO/3 methods. In DMSO and THF solution the test compounds exist predominantly as 2-aryl-4-hydroxy-6H-1,3-oxazin-6-ones. The para substituent in the benzene ring does not affect the composition of the tautomer mixture significantly.

Zakhs, V.E.; Yakovlev, I.P.; Smorygo, N.A.; Gindin, V.A.; Ivin, B.A.

1987-09-01

276

High-level expression of a novel amine-synthesizing enzyme, N-substituted formamide deformylase, in Streptomyces with a strong protein expression system.  

Science.gov (United States)

N-substituted formamide deformylase (NfdA) from Arthrobacter pascens F164 is a novel deformylase involved in the metabolism of isonitriles. The enzyme catalyzes the deformylation of an N-substituted formamide, which is produced from the corresponding isonitrile, to yield the corresponding amine and formate. The nfdA gene from A. pascens F164 was cloned into different types of expression vectors for Escherichia coli and Streptomyces strains. Expression in E. coli resulted in the accumulation of an insoluble protein. However, Streptomyces strains transformed with a P(nitA)-NitR system, which we very recently developed as a regulatory gene expression system for streptomycetes, allowed the heterologous overproduction of NfdA in an active form. When Streptomyces lividans TK24 transformed with pSH19-nfdA was cultured under the optimum conditions, the NfdA activity of the cell-free extract amounted to 8.5 U/mg, which was 29-fold higher than that of A. pascens F164. The enzyme also comprised approximately 20% of the total extractable cellular protein. The recombinant enzyme was purified to homogeneity and characterized. The expression system established here will allow structural analysis and mutagenesis studies of NfdA. PMID:15721791

Fukatsu, Hiroshi; Herai, Sachio; Hashimoto, Yoshiteru; Maseda, Hideaki; Higashibata, Hiroki; Kobayashi, Michihiko

2005-03-01

277

Synthesis of Novel 1-[(2,6-Dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4-carbaldehydes  

Digital Repository Infrastructure Vision for European Research (DRIVER)

A series of novel 1-[(2,6-dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4-carbaldehydes 6a-i were synthesized using the Vilsmeier-Haack reagent. The structures of all the title compounds have been confirmed by elemental analysis, 1H-NMR and 13C-NMR and in addition, the structure of intermedi...

Huanan Hu; Changhua Ge; Lisheng Ding; Anjiang Zhang

278

3-Aryl-4-hydroxyquinolin-2(1H)-one derivatives as type I fatty acid synthase inhibitors.  

UK PubMed Central (United Kingdom)

A series of 3-aryl-4-hydroxyquinolin-2(1H)-ones with fatty acid synthase inhibitory activity was prepared. Starting from a derivative with an IC(50) = 1.4 microM, SAR studies led to compounds with more than 70-fold increase in potency (IC(50) < 20 nM).

Rivkin A; Kim YR; Goulet MT; Bays N; Hill AD; Kariv I; Krauss S; Ginanni N; Strack PR; Kohl NE; Chung CC; Varnerin JP; Goudreau PN; Chang A; Tota MR; Munoz B

2006-09-01

279

Synthesis and anticonvulsant activity of some potent 5,6-bis aryl 1,2,4-triazines  

Digital Repository Infrastructure Vision for European Research (DRIVER)

In the present research, a series of 5,6-bis aryl 1,2,4-triazines 5a~5f were synthesized by condensation of various benzils 4a~4f with aminoguanidine bicarbonate and were screened in vivo, for their anticonvulsant and neurotoxicity studies. Compounds 5a, 5b and 5d were found to be potent molecules o...

Mallikarjuna, B.P.; Suresh Kumar, G.V.; Sastry, B.S.; Nagaraj,; Manohara, K.P.

280

Gold(I)-catalyzed rearrangement of N-aryl 2-alkynylazetidines to pyrrolo[1,2-a]indoles.  

UK PubMed Central (United Kingdom)

Various N-aryl-2-alkynylazetidines were very efficiently converted to pyrrolo[1,2-a]indoles with gold catalysts, especially the 2-biphenyl-dicyclohexylphosphino-gold(I) hexafluoroantimonate, in dichloromethane at room temperature. Additionally, two formal syntheses of bioactive non-natural compounds, i.e. 7-methoxymitosene and an 5-HT(2C) receptor agonist, have been achieved.

Kern N; Hoffmann M; Blanc A; Weibel JM; Pale P

2013-02-01

 
 
 
 
281

Reactions of 5-aryl-furan-2,3-diones with acylmethylenetriphenylphosphoranes: synthesis and biological activity of 3(2H)-furanone derivatives.  

UK PubMed Central (United Kingdom)

The Wittig reaction of 5-aryl-furan-2,3-diones 1 with acylmethylenetriphenylphosphoranes 2 conducted by heating under reflux in benzene solutions, proceeded regiospecifically to afford 2-acylmethylene-5-aryl-3(2H)-furanones 5 in good yields. When the starting compounds 1 and 2 were allowed to react at room temperature, the stable intermediate 5-aryl-2-hydroxy-2-triphenylphosphoranylidenemethyl-3(2H)-furanone s 15 were yielded. The latter adducts underwent triphenylphosphine oxide elimination on heating to form the same olefins 5. The structural assignments of the synthesized compounds were made on the basis of their spectral data and X-ray analysis for 5a. Some of the compounds obtained exhibit antimicrobial activity and one compound of the 3(2H)-furanone series exhibited anticonvulsant activity.

Kozminykh VO; Igidov NM; Kozminykh EN; Aliev ZG

1993-02-01

282

N-Substituted-3-chloro-2-azetidinones: Synthesis and characterization of new novel anti-inflammatory agents  

Directory of Open Access Journals (Sweden)

Full Text Available Various substituted 4-(m-hydroxy-p-methoxy phenyl)-1-[(6'-fluoro-7'-substituted (1,3)-benzothiazol-2'-yl) amido-2-phenyl]-3-chloro azetidin–2–one containing different functional groups have been synthesized by treating fluorochloroaniline with KSCN in presence of bromine in glacial acetic acid and ammonia to get 2-amino-6-fluoro-7-chloro-(1,3)-benzothiazole, which was treated with anthranillic acid in presence of dry pyridine to get 2-amino-N-(6-fluoro-7-chloro-(1,3)-benzothiazol-2-yl) benzamide. To the above, refluxed with vanillin and alcohol in presence of Conc.HCl to get 2-(3-hydroxy-4-methoxy benzylidene amino phenyl amido)-6-fluoro-7-chloro-(1, 3)-benzothiazole or Schiff’s base. A Solution of Schiff’s base in 1,4-dioxane was added to well-stirred mixture of chloroacetyl chloride and triethylamine to get Azetidinone. To the above product different primary and secondaryaromatic amines in presence of DMF were treated to get newly targeted compound through replacing at 7th position chlorine.The lead compounds were characterized by melting point, TLC, calculated elemental analysis, UV, IR and 1H NMR spectral studies. The compounds were tested for anti-inflammatory activity (in-vitro) by protein denaturation method and showed significant activity at low and high concentration compared to standard; still further studies are requested.

Vijay Kumar, M.M.J; Nagaraja, T.S; Shameer, H; Jayachandran, E; Sreenivasa, G.M

2009-01-01

283

Effect of N-substitution in multinuclear complexes allows interplay between magnetic states and multistability investigated by Moessbauer spectroscopy  

Energy Technology Data Exchange (ETDEWEB)

A series of pentadentate ligands N-X-{sup 5}LH{sub 2} (X = H, Methyl, Benzyl) N-X-saldptn (4-X-N,N'-bis(1-hydroxy-2-benzylidene)-1,7-diamino-4-azaheptane) has been prepared by a Schiff base condensation between 1,7-diamino-4-X-azaheptane and salicylaldehyde. Complexation with Fe(III) yields a series of high-spin (S = 5/2) complexes of [Fe{sup III}(N-X-{sup 5}L)Cl]. Such precursors were combined with [Mo(CN){sub 8}]{sup 4-} and a series of blue nonanuclear cluster compounds [Mo{sup IV}{l_brace}(CN)Fe{sup III}(N-X-{sup 5}L){r_brace}{sub 8}]Cl{sub 4} resulted. Such star-shaped nonanuclear compounds are high-spin systems at room temperature. On cooling to 10 K some of the iron(III) centers switched to the low-spin state as proven by Moessbauer spectra, i.e. multiple electronic transitions. Parts of the compounds perform a high-spin to high-spin transition. Under light irradiation the populations are altered slightly.

Renz, F., E-mail: Franz.Renz@uni-mainz.de; Hill, D.; Kerep, P.; Klein, M.; Mueller-Seipel, R.; Werner, F. [Johannes Gutenberg-University, Institut fuer Anorganische Chemie und Analytische Chemie (Germany)

2006-02-15

284

Preparation of Peptide p-Nitroanilides using an Aryl Hydrazine Solid Support  

Energy Technology Data Exchange (ETDEWEB)

Peptide p-nitroanilides are useful compounds for studying protease activity, however the poor nucleophilicity of p-nitroaniline makes their preparation difficult. We describe a new efficient approach for the Fmoc-based synthesis of peptide p-nitroanilides using an aryl hydrazine resin. Mild oxidation of the peptide hydrazide resin yields a highly reactive acyl diazene, which efficiently reacts with weak nucleophiles. We have prepared several peptide p-nitroanilides, including substrates for the Lethal Factor protease from B. anthracis.

Kwon, Y; Welsh, K; Mitchell, A R; Camarero, J A

2004-08-05

285

Efficient synthesis of oxygenated terphenyls and other oligomers: sequential arylation reactions through phenol oxidation-rearomatization.  

Science.gov (United States)

One by one: starting from simple phenols, a diverse series of oxygenated terphenyl compounds can be prepared in a concise and practical manner using sequential arylation reactions involving phenol oxidation/rearomatization and quinone monoacetal intermediates. Many of the terphenyl products can be used for preparing well-defined oligomers and, furthermore, contain valuable functional groups that can be transformed for further diversification. PMID:22996418

Dohi, Toshifumi; Kamitanaka, Tohru; Watanabe, Shohei; Hu, Yinjun; Washimi, Naohiko; Kita, Yasuyuki

2012-09-20

286

Cobalt(II)-catalyzed cross-coupling between polyfunctional arylcopper reagents and aryl fluorides or tosylates.  

UK PubMed Central (United Kingdom)

[reaction: see text] Organocopper compounds prepared by the transmetalation of functionalized arylmagnesium halides with CuCN.2LiCl undergo smooth cross-coupling reactions with aryl fluorides and tosylates bearing a carbonyl function in the ortho position in the presence of Co(acac)(2) (7.5 mol %), Bu(4)NI (1 equiv), and 4-fluorostyrene (20 mol %) as promoters in DME/THF/DMPU leading to polyfunctional aromatics or heterocycles.

Korn TJ; Schade MA; Wirth S; Knochel P

2006-02-01

287

Cobalt(II)-catalyzed cross-coupling between polyfunctional arylcopper reagents and aryl fluorides or tosylates.  

Science.gov (United States)

[reaction: see text] Organocopper compounds prepared by the transmetalation of functionalized arylmagnesium halides with CuCN.2LiCl undergo smooth cross-coupling reactions with aryl fluorides and tosylates bearing a carbonyl function in the ortho position in the presence of Co(acac)(2) (7.5 mol %), Bu(4)NI (1 equiv), and 4-fluorostyrene (20 mol %) as promoters in DME/THF/DMPU leading to polyfunctional aromatics or heterocycles. PMID:16468752

Korn, Tobias J; Schade, Matthias A; Wirth, Stefan; Knochel, Paul

2006-02-16

288

Self-immolative aryl phthalate esters.  

UK PubMed Central (United Kingdom)

We report that aryl phthalate esters are robust self-immolative linkers. This linker is easy to conjugate and releases output phenols upon cleaving a fluoride-sensitive mask to yield a benign phthalic acid byproduct, making these linkers potentially useful as fluoride sensors and promising for use in biological and materials applications.

Mahoney KM; Goswami PP; Winter AH

2013-01-01

289

Synthesis of aryl halides via organoborane chemistry  

Energy Technology Data Exchange (ETDEWEB)

A method for the rapid synthesis of a variety of substituted aryl halides by the reaction of organoboranes with halide ions in the presence of chloramine-T is described in detail. The products were purified by column chromatography on silica gel using a mixture of petroleum ether-ethyl acetate as eluent.

Kabalka, G.W.; Sastry, K.A.R.; Sastry, U.; Somayaji, V.

1982-01-01

290

Aryl azide photochemistry in defined protein environments.  

UK PubMed Central (United Kingdom)

A genetically encoded precursor to an aryl nitrene, para-azidophenylalanine, was introduced site specifically into proteins to deduce if distinct environments were capable of caging a reactive organic intermediate. Following photolysis of mutant T4 lysozyme or green fluorescent proteins, EPR spectra showed, respectively, the presence of a triplet nitrene and an anilino radical.

Morris JL; Reddington SC; Murphy DM; Jones DD; Platts JA; Tippmann EM

2013-02-01

291

Alkyl and aryl neoalkanamides: highly effective insect repellents.  

UK PubMed Central (United Kingdom)

Alkyl and aryl neoalkanamides with a total carbon number between 11 and 14, or within a molecular weight range between 185 and 227, were highly effective repellents of male German cockroaches, Blattella germanica (L.). Comparison with known repellents showed that members of this unique family of secondary amides are among the most effective and long-lasting repellents of cockroaches examined to date. In assays with females and nymphs of the German cockroach, male American cockroaches, Periplaneta americana (L.), and carpenter ant workers, Camponotus pennsylvanicus (De Geer) methyl neodecanamide, propyl neodecanamide, and methyl neotridecanamide were found highly repellent. Because of their broad spectrum of activity, longevity, and safety, these compounds, along with several other members of this family, have important applications as repellents of nuisance pests and of arthropods of public health importance.

Steltenkamp RJ; Hamilton RL; Cooper RA; Schal C

1992-03-01

292

Hydrolyzable hemoglobin adducts of polyfunctional monocyclic N-substituted arenes as dosimeters of exposure and markers of metabolism  

Energy Technology Data Exchange (ETDEWEB)

Hemoglobin adducts of 10 polyfunctional amino- and nitro-substituted benzenes and toluenes were analyzed: 2,4,6-trinitrotoluene, 2,4- and 2,6-dinitrotoluene. 2-amino-4-nitrotoluene, 4-amino-2-nitrotoluene, 2,4- and 2,6-diaminotoluene, 1,3-dinitrobenzene, 1-amino-3-nitrobenzene, and 1,3-diaminobenzene. A single dose (0.5 mmole/kg) of the test compounds was administered to female Wistar rats by gavage, and blood extracted and hemoglobin prepared after 24 hr. One or more cleavage products could be obtained in each case by hydrolyzing hemoglobin (Hb). Hemoglobin binding indices (HBl); binding (mmole/mole Hbl/dose [mmole/kg]) and the ratios of hydrolyzable adducts were determined. The HBl ranged between <0/.02 and 69.0. The results indicate the in vivo formation of several, convalently bound, hydrolyzable hemoglobin adducts. Conclusion on prevailing metabolic pathways can be drawn. Total binding of several compounds seems sufficient for biomonitoring of human blood samples. These chemicals are considered representative for environmental contamination with explosives of this type, and we propose their Hb adducts be used as dosimeters for human exposure to these suspected carcinogens. 8 refs., 2 figs., 2 tabs.

Zwirner-Baier, I.; Kordowich, F.J.; Neumann, H.G. [Universitaet Wuerzburg (Germany)

1994-10-01

295

Pyridothiophene Compounds  

UK PubMed Central (United Kingdom)

The use of compounds of formula (I) in therapy, particularly for the treatment of a disorder mediated by excessive or inappropriate HSP90 activity formula (I), wherein R2 is a group of formula (IA): -(Ar1)m-(Alk1)p-(Z)r-(Alk2)S-Q (IA) Ar1, Alk1, Z, Alk2 and Q being as defined in the specification m, p, r and s are independently 0 or 1 R3 is hydrogen, an optional substituent, or an optionally substituted (C1-C6)alkyl, aryl or heteroaryl radical and R4 is a carboxylic ester, carboxamide or sulfonamide group or a salt, N-oxide, hydrate, or solvate thereof.

DRYSDALE MARTIN JAMES; DYMOCK BRIAN WILLIAM; BARRIL-ALONSO XAVIER

296

CARBAZOLE COMPOUND AND USE THEREOF  

UK PubMed Central (United Kingdom)

Disclosed is a carbazole compound represented by the formula. In the formula, when m = 1 and n = 0, Ar1, Ar2, Ar3 and X2 each represents a C6-50 aryl group, a C4-50 heteroaryl group X1 represents a C6-50 arylene group R1, R2, R4, R5 and R7 each represents H, a halogen atom, an amino group, a C1-18 alkyl group, a C1-18 alkoxy group, a C6-50 aryl group or a C4-50 heteroaryl group R3 and R6 each represents H, a halogen atom, a C1-18 alkyl group, a C1-18 alkoxy group, a C6-50 aryl group or a C4-50 heteroaryl group and Ar1 and Ar2 as well as Ar3 and X2 may respectively combine together to form a ring. In the formula, when m = 0 and n = 1-3, Ar3, Ar4 and Ar5 each represents a C6-50 aryl group or a C4-50 heteroaryl group X1 represents a C1-18 alkyl group, a C6-50 aryl group or a C4-50 heteroaryl group X2 represents a C6-50 arylene group R1-R7 each represents H, a halogen atom, a C1-18 alkyl group, a C1-18 alkoxy group, a C6-50 aryl group or a C4-50 heteroaryl group and Ar4 and Ar5 may combine together to form a ring. In the formula, when m = n = 0, X1 represents a C1-18 alkyl group, a C6-50 aryl group or a C4-50 heteroaryl group Ar3 and X2 each represents a C6-50 aryl group or a C4-50 heteroaryl group R2 represents H, a halogen atom, a C1-18 alkyl group or a C1-18 alkoxy group and R1 and R3-R7 each represents H, a halogen atom, a C1-18 alkyl group, a C1-18 alkoxy group, a C6-50 aryl group or a C4-50 heteroaryl group. The carbazole compound is useful as a material for an organic EL element.

MATSUMOTO NAOKI; MIYAZAKI TAKANORI; ISHIKAWA SHINICHI

297

Synthesis and evaluation of N-substituted cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamines as high affinity sigma receptor ligands. Identification of a new class of highly potent and selective sigma receptor probes.  

UK PubMed Central (United Kingdom)

Certain benzeneacetamides [(-)- and (+)-cis-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl) cyclohexyl]benzeneacetamide] were recently reported to be potent sigma receptor ligands. In order to determine whether efficacy for the sigma receptor could be improved, a series of compounds related to the benzeneacetamides, N-substituted cis-2-(1-pyrrolidinyl)-N-methylcyclohexylamines, were synthesized and their structure-activity requirements were determined. The compounds were synthesized by starting with the previously reported (+/-)-, 1S,2R-(+)-, and 1R,2S-(-)-cis-2-(1-pyrrolidinyl)-N-methylcyclohexylamines. Analysis of sigma ([3H](+)-3-PPP), kappa ([3H]bremazocine and [3H]U69,593), dopamine-d2 ([3H](-)-sulpiride), and phencyclidine (PCP) ([3H]TCP) receptor binding in guinea pig brain revealed a number of highly potent and selective sigma receptor ligands. Notably, 1S,2R-cis-(-)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]-(2-naphthyl) acetamide [(-)-29] (Ki = 8.66 +/- 0.35 nM), (+/-)-cis-2-amino-4,5-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl] benzeneacetamide [(+/-)-17] (Ki = 11 +/- 3 nM), 1S,2R-(-)-cis-N-methyl-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl ) cyclohexylamine [(-)-44] (Ki = 1.3 +/- 0.3 nM), and 1R,2S-(+)-cis-N-methyl-N-[2-(3,4-dichlorophenyl)ethyl]-2-(1-pyrrolidinyl ) cyclohexylamine. [(+)-44] (Ki = 6 +/- 3 nM) exhibited very high affinity at sigma receptors, by displacement of [3H]-(+)-3-(3-hydroxyphenyl)-N-(1-propyl)piperidine [( 3H]-(+)-3-PPP). These compounds showed insignificant affinity for kappa, dopamine, or PCP receptors, making them valuable tools for the study of sigma receptors. Furthermore, these compounds also exhibited enantioselectivity ranging from 5-fold for (+)- and (-)-44 to 160-fold for (+)- and (-)-29. Several other compounds showed equivalent selectivity but displayed lower sigma receptor affinity.

de Costa BR; Rice KC; Bowen WD; Thurkauf A; Rothman RB; Band L; Jacobson AE; Radesca L; Contreras PC; Gray NM

1990-11-01

298

PYRENE COMPOUND AND ORGANIC LIGHT EMITTING DEVICE  

UK PubMed Central (United Kingdom)

An object of the present invention is to provide a novel pyrene compound. Provided is a pyrene compound represented by the following general formula (I): wherein: R1 and R2 each represent a substituted or unsubstituted alkyl group; and Ar1, Ar2, Ar3, and Ar4 each represent a substituted or unsubstituted aryl group and the like.

SUZUKI KOICHI; YAMADA NAOKI; UENO KAZUNORI

299

Liver X receptor agonists with selectivity for LXRbeta; N-aryl-3,3,3-trifluoro-2-hydroxy-2-methylpropionamides.  

UK PubMed Central (United Kingdom)

The synthesis and SAR of a new series of LXR agonist is reported. The N-Aryl-3,3,3-trifluoro-2-hydroxy-2-methyl-propionamide hits were found in a limited screen of the AstraZeneca compound collection. The effort to optimize these hits into LXRbeta selectivity is described. Compound 20 displayed desirable pharmacokinetic profile and up regulation of ABCA1 and ABCG1 mRNA in the brain were achieved when evaluated in vivo in mice.

Swahn BM; Macsari I; Viklund J; Ohberg L; Sjödin J; Neelissen J; Lindquist J

2009-04-01

300

Cu-mediated N-arylation of 1,2,3-triazin-4-ones: synthesis of fused triazinone derivatives as potential inhibitors of chorismate mutase.  

UK PubMed Central (United Kingdom)

A rapid and direct access to N-aryl substituted fused triazinone derivatives has been accomplished via N-arylation of 1,2,3-triazin-4-one ring involving a Cu-mediated coupling between triazinone derivatives and aryl boronic acids. A combination of Cu(OAc)(2)-Et(3)N in 1,2-dichloroethane was found to be effective and various fused triazinone derivatives have been prepared by using this methodology. Molecular structure of a representative compound was confirmed by single crystal X-ray diffraction study. The scope and limitations of this reaction is discussed. Some of the compounds synthesized were tested for chorismate mutase inhibitory properties in vitro. The in vitro dose response study of an active compound is presented.

Shiva Kumar K; Adepu R; Sandra S; Rambabu D; Rama Krishna G; Malla Reddy C; Misra P; Pal M

2012-01-01

 
 
 
 
301

Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols.  

Science.gov (United States)

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C-N and C-O bond formation have been developed. The C-N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs(2)CO(3), dioxane and palladium catalyst precursors Pd(OAc)(2)/Pd(2)(dba)(3). The combination of Pd(OAc)(2), Xantphos, K(2)CO(3) and dioxane was found to be crucial for the C-O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives. PMID:23209536

Surasani, Rajendra; Kalita, Dipak; Rao, A V Dhanunjaya; Chandrasekhar, K B

2012-11-19

302

Palladium-catalyzed C-N and C-O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols.  

UK PubMed Central (United Kingdom)

Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C-N and C-O bond formation have been developed. The C-N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs(2)CO(3), dioxane and palladium catalyst precursors Pd(OAc)(2)/Pd(2)(dba)(3). The combination of Pd(OAc)(2), Xantphos, K(2)CO(3) and dioxane was found to be crucial for the C-O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

Surasani R; Kalita D; Rao AV; Chandrasekhar KB

2012-01-01

303

Multicomplex-based pharmacophore-guided 3D-QSAR studies of N-substituted 2'-(aminoaryl)benzothiazoles as Aurora-A inhibitors.  

UK PubMed Central (United Kingdom)

Aurora-A has been known as one of the most important targets for cancer therapy, and some Aurora-A inhibitors have entered clinical trails. In this study, combination of the ligand-based and structure-based methods is used to clarify the essential quantitative structure-activity relationship of known Aurora-A inhibitors, and multicomplex-based pharmacophore-guided method has been suggested to generate a comprehensive pharmacophore of Aurora-A kinase based on a collection of crystal structures of Aurora-A-inhibitor complex. This model has been successfully used to identify the bioactive conformation and align 37 structurally diverse N-substituted 2'-(aminoaryl)benzothiazoles derivatives. The quantitative structure-activity relationship analyses have been performed on these Aurora-A inhibitors based on multicomplex-based pharmacophore-guided alignment. These results may provide important information for further design and virtual screening of novel Aurora-A inhibitors.

He G; Qiu M; Li R; Ouyang L; Wu F; Song X; Cheng L; Xiang M; Yu L

2012-06-01

304

Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols  

Directory of Open Access Journals (Sweden)

Full Text Available Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives.

Rajendra Surasani; Dipak Kalita; A. V. Dhanunjaya Rao; K. B. Chandrasekhar

2012-01-01

305

C(aryl)-O Bond Formation from Aryl Methanesulfonates via Consecutive Deprotection and SNAr Reactions with Aryl Halides in an Ionic Liquid  

Directory of Open Access Journals (Sweden)

Full Text Available An efficient K3PO4-mediated synthesis of unsymmetrical diaryl ethers using the ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) as solvent has been developed. The procedure involves consecutive deprotection of aryl methane-sulfonates and a nucleophilic aromatic substitution (SNAr) with activated aryl halides.

Hui Xu; Yang Chen

2007-01-01

306

Palladium-Catalyzed alpha-Arylation of Tetramic Acids  

DEFF Research Database (Denmark)

A mild, racemization-free, palladium-Catalyzed alpha-arylation of tetramic acids (2,4-pyrrolidinediones) has been developed. Various amino acid-derived tetramic acids were cleanly arylated by treatment with 2 mol % of Pd(OAc)(2), 4 mol % of a sterically demanding biaryl phosphine, 2.3 equiv of K2CO3 or K3PO4, and aryl chlorides, bromides, or triflates in THF. With conventional heating, conversions >95% could be attained after 1 h at 80 degrees C, whereas microwave-induced heating led to much shorter reaction times (5 min at 110 degrees C). The electron density of the aryl electrophile had no effect on their reactivity: both electron-rich and electron-poor aryl chlorides and bromides or triflates led to good yields. Ortho-substituted aryl halides and heteroaryl halides, however, did not undergo the title reaction.

Storgaard, Morten; Dorwald, F. Z.

2009-01-01

307

Preparation of aryl-bridged polysilsesquioxane aerogels  

Energy Technology Data Exchange (ETDEWEB)

We report the preparation of a new class of organic/inorganic hybrid aerogels from aryl-bridged polysilsesquioxanes. 1,4- Bis(triethoxysilyl)benzene and 4,4{prime}-bis(triethoxysilyl)- biphenyl were sol-gel processed to form phenyl- and biphenyl-bridged polysilsesquioxane gels. The gels were then dried using supercritical carbon dioxide extraction. It was discovered that aryl-bridged polysilsesquioxane aerogels are indeed formed, but with a pronounced influence on surface area from the reaction conditions used in preparing the initial gels. Specifically, high surface area aerogels (up to 1750 m{sup 2}/g) are obtained from gels prepared with either acid or base catalysts. With reduced concentrations of base catalyst, however, supercritical processing afforded phenyl-bridge xerogel-like materials. The materials were characterized by nitrogen sorption surface analysis and by transmission electron microscopy. 8 refs., 5 figs., 1 tab.

Loy, D.A.; Russick, E.M. [Sandia National Labs., Albuquerque, NM (United States); Shea, K.J. [California Univ., Irvine, CA (United States). Dept. of Chemistry

1991-12-31

308

Preparation of aryl-bridged polysilsesquioxane aerogels  

Energy Technology Data Exchange (ETDEWEB)

We report the preparation of a new class of organic/inorganic hybrid aerogels from aryl-bridged polysilsesquioxanes. 1,4- Bis(triethoxysilyl)benzene and 4,4{prime}-bis(triethoxysilyl)- biphenyl were sol-gel processed to form phenyl- and biphenyl-bridged polysilsesquioxane gels. The gels were then dried using supercritical carbon dioxide extraction. It was discovered that aryl-bridged polysilsesquioxane aerogels are indeed formed, but with a pronounced influence on surface area from the reaction conditions used in preparing the initial gels. Specifically, high surface area aerogels (up to 1750 m{sup 2}/g) are obtained from gels prepared with either acid or base catalysts. With reduced concentrations of base catalyst, however, supercritical processing afforded phenyl-bridge xerogel-like materials. The materials were characterized by nitrogen sorption surface analysis and by transmission electron microscopy. 8 refs., 5 figs., 1 tab.

Loy, D.A.; Russick, E.M. (Sandia National Labs., Albuquerque, NM (United States)); Shea, K.J. (California Univ., Irvine, CA (United States). Dept. of Chemistry)

1991-01-01

309

PALLADIUM CATALYZED COUPLING OF ARYL HALIDES WITH ARYLHALOSILANES IN AIR AND WATER. (R828129)  

Science.gov (United States)

In the presence of a palladium catalyst, various aryl halides reacted with arylhalosilanes in aqueous media and under an air atmosphere to give the corresponding unsymmetrical aryl–aryl coupling products conveniently. ...

310

Photooxidation of mixed aryl and biarylphosphines.  

UK PubMed Central (United Kingdom)

Arylphosphines and dialkylbiarylphosphines react with singlet oxygen to form phosphine oxides and phosphinate esters. For mixed arylphosphines, the most electron-rich aryl group migrates to form the phosphinate, while for dialkylbiarylphosphines migration of the alkyl group occurs. Dialkylbiarylphosphines also yield arene epoxides, especially in electron-rich systems. Phosphinate ester formation is increased at high temperature, while protic solvents increase the yield of epoxide. The product distribution provides evidence for Buchwald's recent conformational model for the aerobic oxidation of dialkylbiarylphosphines.

Zhang D; Celaje JA; Agua A; Doan C; Stewart T; Bau R; Selke M

2010-07-01

311

Synthesis and antileishmanial activity of new 1-Aryl-1H-Pyrazole-4- carboximidamides derivatives  

International Nuclear Information System (INIS)

[en] Chemotherapy for leishmaniasis, diseases caused by protozoa of the genus Leishmania, remains inefficient in several treatments. So there is a need to search for new drugs. In this work, we have synthesized 1-aryl-1H-pyrazole-4-carboximidamides derivatives and evaluated antileishmanial activities in vitro, as well as cytotoxic effects. Structure-activity relationship (SAR) studies were carried out with all the compounds of the series. Compound 2 showed an activity profile that can be improved through medicinal chemistry strategies. (author)

2011-01-01

312

Synthesis of aryl b-N-acetylglucosamine desmodified at C-6 as potential antimicrobial agents  

International Nuclear Information System (INIS)

We report herein the synthesis of aryl beta-N-acetylglucosaminides containing azido, amino and acetamido groups at C-6 as potential antimicrobial agents. It was expected that these compounds could interfere with the biosynthesis and/or biotransformation of Nacetylglucosamine in fungi and bacteria. None of the compounds showed antimicrobial activity against bacteria (Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa), filamentous fungus (Aspergillus niger) and yeasts (Saccharomyces cerevisae, Candida albicans and Candida tropicallis), at the concentration of 1 mg/mL in agar diffusion assay. (author)

2008-01-01

313

Synthesis of 3-aryl-5-decapentyl-1,2,4-oxadiazoles possessing antiinflammatory and antitumor properties.  

Science.gov (United States)

A simple, convenient and straightforward synthesis of 3-aryl-1,2,4-oxadiazoles 4a-f from arylamidoximes 1a-f and palmitic acid 2 is described. Compounds 4a-f are non-lethal in mice at four times the therapeutic dose (i.p., LD50>1 g kg(-1) of the animals' body weight). These heterocycles have been found to possess antiinflammatory property similar to aspirin and ibuprofen. Three compounds, viz., 4a, d, e have also been evaluated for antitumor activity, where 4d exhibited an excellent activity comparable to lapachol. PMID:16242685

Bezerra, Natércia M Miranda; De Oliveira, Shalom P; Srivastava, Rajendra M; Da Silva, Joel R

2005-10-20

314

Pyrolysis studies of organic oxygenates 3. High temperature rearrangement of aryl alkyl ethers  

Energy Technology Data Exchange (ETDEWEB)

Thermal chemistry pathways of aryl alkyl ethers have been investigated under coal conversion-like conditions. Anisole is a thermally reactive compound having an oxygen functionality found in such coal precursors as lignins. Pyrolysis of anisoles was carried out using small batch autoclaves. Under thermolysis conditions anisole yielded a product distribution strongly dependent upon experimental parameters. Phenol, methane, CO and benzaldehyde are the low molecular weight products and polyphenyls and polyethers are the predominant high molecular weight products. The generation of CO is explained by a high temperature rearrangement of the phenyl group from O- to C- followed by rapid thermal decarbonylation of the benzaldehyde. Carbon monoxide formation from aryl alkyl ether can thus be an important mechanistic pathway in coal conversion processes. By investigating the rearrangement using para-fluoroanisole it was shown that this rearrangement proceeds via a threecentered intermediate to para-fluorobenzaldehyde. No meta isomer was observed.

Schlosberg, R.H.; Ashe, T.R.; Danik, J.A.; Dupre, G.D.; Kurs, A.; Olmstead, W.N.; Szajowski, P.F.

1983-06-01

315

Synthesis and antifungal activity of 1-aryl-3-phenethylamino-1-propanone hydrochlorides and 3-aroyl-4-aryl-1-phenethyl-4-piperidinols.  

Science.gov (United States)

Mono-Mannich bases, 1-aryl-3-phenethylamino-1-propanone hydrochlorides, 1a, 2a, 3a, 4a, 5a, 6a, 7a, 8a, 9a, and semi-cyclic mono-Mannich bases, 3-aroyl-4-aryl-1-phenethyl-4-piperidinols, 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, were synthesized by a non-classical Mannich reaction. The aryl part was: C(6)H(5 )for 1a, 1b; 4-CH(3)C(6)H(4) for 2a, 2b; 4-CH(3)OC(6)H(4 )for 3a, 3b; 4-ClC(6)H(4 )for 4a, 4b; 4-FC(6)H(4) for 5a, 5b; 4-BrC(6)H(4) for 6a, 6b; 2,4-(Cl)(2)C(6)H(3) for 7a, 7b; 4-NO(2)C(6)H(4 )for 8a, 8b; and C(4)H(3)S(2-yl) i. e., 2-thienyl for 9a, 9b. Piperidinol compounds 2b, 3b, 4b, 5b, 7b, 8b, and 9b are reported here for the first time. The synthesized compounds were tested against seven types of plant pathogenic fungi and three types of human pathogenic fungi using the agar dilution assay. Itraconazole was tested against Candida parapsilosis as the reference compound, while Nystatin was tested as the reference compound against the other fungi. Compounds 1a, 1b, 2a, 4a, 4b, 5a, 5b, 6a, 7a, 8a, 9a, and 9b can be selected as model compounds to develop new antifungal agents against the human pathogen Microsporum canis. Compounds 8a and 8b, which had a similar antifungal activity compared with the reference compound Nystatin against the plant pathogen Aspergillus flavus, can serve as model compounds to develop new antifungal agents to solve agricultural problems. PMID:20232370

Mete, Ebru; Ozelgul, Canan; Kazaz, Cavit; Yurdakul, Dilsad; Sahin, Fikrettin; Inci Gul, Halise

2010-05-01

316

Synthesis and antifungal activity of 1-aryl-3-phenethylamino-1-propanone hydrochlorides and 3-aroyl-4-aryl-1-phenethyl-4-piperidinols.  

UK PubMed Central (United Kingdom)

Mono-Mannich bases, 1-aryl-3-phenethylamino-1-propanone hydrochlorides, 1a, 2a, 3a, 4a, 5a, 6a, 7a, 8a, 9a, and semi-cyclic mono-Mannich bases, 3-aroyl-4-aryl-1-phenethyl-4-piperidinols, 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, 9b, were synthesized by a non-classical Mannich reaction. The aryl part was: C(6)H(5 )for 1a, 1b; 4-CH(3)C(6)H(4) for 2a, 2b; 4-CH(3)OC(6)H(4 )for 3a, 3b; 4-ClC(6)H(4 )for 4a, 4b; 4-FC(6)H(4) for 5a, 5b; 4-BrC(6)H(4) for 6a, 6b; 2,4-(Cl)(2)C(6)H(3) for 7a, 7b; 4-NO(2)C(6)H(4 )for 8a, 8b; and C(4)H(3)S(2-yl) i. e., 2-thienyl for 9a, 9b. Piperidinol compounds 2b, 3b, 4b, 5b, 7b, 8b, and 9b are reported here for the first time. The synthesized compounds were tested against seven types of plant pathogenic fungi and three types of human pathogenic fungi using the agar dilution assay. Itraconazole was tested against Candida parapsilosis as the reference compound, while Nystatin was tested as the reference compound against the other fungi. Compounds 1a, 1b, 2a, 4a, 4b, 5a, 5b, 6a, 7a, 8a, 9a, and 9b can be selected as model compounds to develop new antifungal agents against the human pathogen Microsporum canis. Compounds 8a and 8b, which had a similar antifungal activity compared with the reference compound Nystatin against the plant pathogen Aspergillus flavus, can serve as model compounds to develop new antifungal agents to solve agricultural problems.

Mete E; Ozelgul C; Kazaz C; Yurdakul D; Sahin F; Inci Gul H

2010-05-01

317

Significance of aryl ether cleavage in kraft delignification of softwood  

Energy Technology Data Exchange (ETDEWEB)

The kinetics of kraft delignification of soft-wood and of aryl ether cleavage reactions in lignin as obtained in studies in the initial phase of kraft pulping may well be ascribed to cleavage of alfa-aryl ether and beta-aryl ether linkages in phenolic aryl propane units. The rate of lignin dissolution during the main (bulk) phase is of the same magnitude as the rate of the cleavage of beta-aryl ether linkages in non-phenolic benzylalcoholic aryl propane units. Furthermore, the rate of this cleavage is strongly dependent, like the rate of bulk delignification, on the concentration of hydroxide ions in the pulping liquor. Hydrosulfide ions do not affect cleavage of non-phenolic beta-aryl ether linkages, but increase the extent of cleavage of such linkages in phenolic aryl propane units. On the basis of these observations a delignification mechanism for kraft pulping is discussed. It is proposed that the cleavage of beta-aryl ether linkages in non-phenolic benzyl alcoholic structures is an important factor in determining the rate of the bulk delignification.

Ljungagren, S.

1980-09-01

318

Rh(I)-Catalyzed Direct Arylation of Azines.  

UK PubMed Central (United Kingdom)

The Rh(I)-catalyzed direct arylation of azines has been developed. Quinolines and 2-substituted pyridines couple with aryl bromides to efficiently afford ortho-arylated azine products using the commercially available and air-stable catalyst [RhCl(CO)(2)](2). Electron-deficient and electron-rich aromatic bromides couple in good yields, and hydroxyl, chloro, fluoro, trifluoromethyl, ether, and ketone functionalities are compatible with the reaction conditions. Aroyl chlorides also serve as effective azine coupling partners to give ortho-arylation products via a decarbonylation pathway.

Berman AM; Bergman RG; Ellman JA

2010-10-01

319

Rh(I)-Catalyzed Direct Arylation of Azines  

Science.gov (United States)

The Rh(I)-catalyzed direct arylation of azines has been developed. Quinolines and 2-substituted pyridines couple with aryl bromides to efficiently afford ortho-arylated azine products using the commercially available and air stable catalyst [RhCl(CO)2]2. Electron-deficient and rich aromatic bromides couple in good yields, and hydroxyl, chloro, fluoro, trifluoromethyl, ether and ketone functionality are compatible with the reaction conditions. Aroyl chlorides also serve as effective azine coupling partners to give ortho-arylation products via a decarbonylation pathway.

Berman, Ashley M.; Bergman, Robert G.; Ellman, Jonathan A.

2011-01-01

320

Stereoselective synthesis of unsymmetrical ?,?-diarylacrylates by a Heck-Matsuda reaction: versatile building blocks for asymmetric synthesis of ?,?-diphenylpropanoates, 3-aryl-indole, and 4-aryl-3,4-dihydro-quinolin-2-one and formal synthesis of (-)-indatraline.  

UK PubMed Central (United Kingdom)

?,?-Disubstituted ?,?-unsaturated esters may serve as valuable derivatives for the preparation of other highly functionalized systems found in many natural products and marketed drugs. The stereoselective synthesis of unsymmetrical ?,?-diarylacrylate compounds possessing two similar aromatic groups remains a substantial challenge. A simple and convenient stereoselective protocol for the preparation of ?,?-disubstituted acrylates via a Heck-Matsuda reaction is reported. Good to high yields were accomplished by a "ligand-free" Pd-catalyzed arylation reaction of cinnamate esters with arenediazonium tetrafluoroborates. Both electron-deficient and electron-rich arenediazonium salts could be employed as arylating reagents, and cinnamate esters were generally more reactive when substituted with an electron-donating group. The overall methodology is highly stereoselective, and this attribute was taken advantage of in the asymmetric Cu-catalyzed 1,4 reduction reaction to provide ?,?-diarylpropanoates in high enantioselectivities. The synthesis of a 3-aryl indole and a chiral 4-aryl-2-quinolone from ?,?-diarylacrylates was achieved by cyclization in the presence of a diphosphine ligated CuH catalyst. A convenient route for the asymmetric formal synthesis of the psychoactive compound (-)-Indatraline is also presented.

Taylor JG; Correia CR

2011-02-01

 
 
 
 
321

Stereoselective synthesis of unsymmetrical ?,?-diarylacrylates by a Heck-Matsuda reaction: versatile building blocks for asymmetric synthesis of ?,?-diphenylpropanoates, 3-aryl-indole, and 4-aryl-3,4-dihydro-quinolin-2-one and formal synthesis of (-)-indatraline.  

Science.gov (United States)

?,?-Disubstituted ?,?-unsaturated esters may serve as valuable derivatives for the preparation of other highly functionalized systems found in many natural products and marketed drugs. The stereoselective synthesis of unsymmetrical ?,?-diarylacrylate compounds possessing two similar aromatic groups remains a substantial challenge. A simple and convenient stereoselective protocol for the preparation of ?,?-disubstituted acrylates via a Heck-Matsuda reaction is reported. Good to high yields were accomplished by a "ligand-free" Pd-catalyzed arylation reaction of cinnamate esters with arenediazonium tetrafluoroborates. Both electron-deficient and electron-rich arenediazonium salts could be employed as arylating reagents, and cinnamate esters were generally more reactive when substituted with an electron-donating group. The overall methodology is highly stereoselective, and this attribute was taken advantage of in the asymmetric Cu-catalyzed 1,4 reduction reaction to provide ?,?-diarylpropanoates in high enantioselectivities. The synthesis of a 3-aryl indole and a chiral 4-aryl-2-quinolone from ?,?-diarylacrylates was achieved by cyclization in the presence of a diphosphine ligated CuH catalyst. A convenient route for the asymmetric formal synthesis of the psychoactive compound (-)-Indatraline is also presented. PMID:21241065

Taylor, Jason G; Correia, Carlos Roque D

2011-01-11

322

N-Heterocyclic carbene-palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides.  

UK PubMed Central (United Kingdom)

New Pd-NHC complexes have been synthesized and employed for palladium-catalyzed direct arylation of pyrrole derivatives by using electron-deficient aryl chlorides as coupling partners. The desired coupling products were obtained in moderate to good yields by using 1 mol % of these air-stable palladium complexes. This is an advantage compared to the procedures employing air-sensitive phosphines, which have been previously shown to promote the coupling of aryl chlorides with heteroarenes.

Ozdemir I; Gürbüz N; Kalo?lu N; Do?an O; Kalo?lu M; Bruneau C; Doucet H

2013-01-01

323

N-Heterocyclic carbene–palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides  

Directory of Open Access Journals (Sweden)

Full Text Available New Pd–NHC complexes have been synthesized and employed for palladium-catalyzed direct arylation of pyrrole derivatives by using electron-deficient aryl chlorides as coupling partners. The desired coupling products were obtained in moderate to good yields by using 1 mol % of these air-stable palladium complexes. This is an advantage compared to the procedures employing air-sensitive phosphines, which have been previously shown to promote the coupling of aryl chlorides with heteroarenes.

Ismail Özdemir; Nevin Gürbüz; Nazan Kalo?lu; Öznur Do?an; Murat Kalo?lu; Christian Bruneau; Henri Doucet

2013-01-01

324

FLUORANTHENE POLYMERIC COMPOUND  

UK PubMed Central (United Kingdom)

Disclosed is a polymeric compound having a constitutional unit represented by general formula (1). [In the formula, Ar1 represents an aromatic hydrocarbon group or an aromatic heterocyclic group. E represents a group formed by removing a single hydrogen atom from a compound represented by formula (2) ( in the formula, R1-R10 represent a hydrogen atom, an alkyl group, an aryl group, a monovalent aromatic heterocyclic group or a group represented by - O - RA. RA represents an alkyl group, an alyl group, or a monovalent aromatic heterocyclic group). aa represents an integer of at least 1.

YOSHIDA TOMOYASU; HANAOKA HIDENORI; MORIWAKI SHOTA

325

Synthesis, biological evaluation, 3D-QSAR studies of novel aryl-2H-pyrazole derivatives as telomerase inhibitors.  

UK PubMed Central (United Kingdom)

A series of novel aryl-2H-pyrazole derivatives bearing 1,4-benzodioxan or 1,3-benzodioxole moiety were designed as potential telomerase inhibitors to enhance the ability of aryl-2H-pyrazole derivatives to inhibit telomerase, a target of anticancer. The telomerase inhibition tests showed that compound 16A displayed the most potent inhibitory activity with IC(50) value of 0.9 ?M for telomerase. The antiproliferative tests showed that compound 16A exhibited high activity against human gastric cancer cell SGC-7901 and human melanoma cell B16-F10 with IC(50) values of 18.07 and 5.34 ?M, respectively. Docking simulation showed that compound 16A could bind well with the telomerase active site and act as telomerase inhibitor. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent telomerase inhibitory activity.

Luo Y; Zhang S; Qiu KM; Liu ZJ; Yang YS; Fu J; Zhong WQ; Zhu HL

2013-02-01

326

Solid-phase synthesis and antitumor evaluation of 2,4-diamino-6-aryl-1,3,5-triazines.  

Science.gov (United States)

2,4-Diamino-6-aryl-1,3,5-triazines were synthesized by using a solid-supported approach in which monoarylsubstituted triazines were captured directly from the crude reaction mixture by resin-bound amines. The effects of the synthesized compounds on inhibition activities against tumor cell lines (PC-3, K562, A549, and HO8910) were examined. Most of the obtained compounds demonstrated remarkable antiproliferative activities against K562, PC-3, and HO8910 cell lines. Particularly, compounds 8c exhibited prominent inhibition activity with IC(50) values of 1.01, 2.23, and 1.06 microM, respectively. The structure-activity relationships of 2,4-diamino-6-aryl-1,3,5-triazines are also discussed. PMID:19125569

Hu, Zhang; Ma, Ting; Chen, Zhe; Ye, Ziqi; Zhang, Guolin; Lou, Yijia; Yu, Yongping

2009-03-01

327

Synthesis, characterization and biological evaluation of novel 6-ferrocenyl-4-aryl-2-substituted pyrimidine derivatives.  

UK PubMed Central (United Kingdom)

A new series of 6-ferrocenyl-4-aryl-2-substituted pyrimidines were synthesized and evaluated for in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. Out of 16 compounds 10 compounds have shown IC(50) values in the range of 0.41-1.73 microM and 1.80 microM. Pyrimidine derivatives having thiomethyl group, chloro group and mono-, di-, and trimethoxy substitution, exhibited higher antiamoebic activity than the reference drug metronidazole (IC(50)=1.80 microM). The toxicological studies of these compounds on human kidney epithelial cell line showed that all compounds were non-toxic. 4-(4-Chlorophenyl)-6-ferrocenyl-2-piperidin-1-yl-pyrimidine (4f) was found most active (IC(50)=0.41 microM) and least toxic among all the compounds.

Parveen H; Hayat F; Salahuddin A; Azam A

2010-08-01

328

Design, synthesis and biological evaluation of aryl pyrimidine derivatives as potential leishmanicidal agents.  

UK PubMed Central (United Kingdom)

A series of substituted aryl pyrimidine derivatives was synthesized and evaluated in vitro for their antileishmanial potential against intracellular amastigotes of Leishmania donovani using reporter gene luciferase assay. Among all, 8 compounds showed promising IC50 values ranging from 0.5 to 12.9?M. Selectivity indices (S.I.) of all these compounds are far better than reference drugs, sodium stibogluconate (SSG) and miltefosine. On the basis of good S.I., compounds were further screened for their in vivo antileishmanial activity against L. donovani/hamster model. Compounds 2d, 4a and 4b have shown significant inhibition of parasitic multiplication that is 88.4%, 78.1% and 78.2%, respectively at a daily dose of 50mg/kg×5days, when administered intraperitoneally. Compound 2d is most promising one, which may provide a new lead that could be exploited as a new antileishmanial agent.

Suryawanshi SN; Kumar S; Shivahare R; Pandey S; Tiwari A; Gupta S

2013-09-01

329

Design, synthesis and biological evaluation of aryl pyrimidine derivatives as potential leishmanicidal agents.  

Science.gov (United States)

A series of substituted aryl pyrimidine derivatives was synthesized and evaluated in vitro for their antileishmanial potential against intracellular amastigotes of Leishmania donovani using reporter gene luciferase assay. Among all, 8 compounds showed promising IC50 values ranging from 0.5 to 12.9?M. Selectivity indices (S.I.) of all these compounds are far better than reference drugs, sodium stibogluconate (SSG) and miltefosine. On the basis of good S.I., compounds were further screened for their in vivo antileishmanial activity against L. donovani/hamster model. Compounds 2d, 4a and 4b have shown significant inhibition of parasitic multiplication that is 88.4%, 78.1% and 78.2%, respectively at a daily dose of 50mg/kg×5days, when administered intraperitoneally. Compound 2d is most promising one, which may provide a new lead that could be exploited as a new antileishmanial agent. PMID:23910597

Suryawanshi, S N; Kumar, Santosh; Shivahare, Rahul; Pandey, Susmita; Tiwari, Avinash; Gupta, Suman

2013-06-29

330

Stereoselective synthesis of spiropiperidines as BACE-1 aspartyl protease inhibitors via late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore.  

Science.gov (United States)

A stereoselective synthesis of spiropiperidine compounds, exemplified by compound 1, was developed, which was based upon the late stage N-arylation of a 1,8-diazaspiro[4.5]dec-3-en-2-one pharmacophore. Previously, compound 1 was prepared in low overall yield from piperidinone 2 via the Strecker reaction. A new route was developed, which employed the stereospecific Corey-Link reaction of an enantiomerically pure trichloromethylcarbinol to give a template compound amenable to late stage N-arylation. PMID:23438191

Lee, Che-Wah; Lira, Ricardo; Dutra, Jason; Ogilvie, Kevin; O'Neill, Brian T; Brodney, Michael; Helal, Christopher; Young, Joseph; Lachapelle, Erik; Sakya, Subas; Murray, John C

2013-03-04

331

AZABORINE COMPOUNDS AS HOST MATERIALS AND DOPANTS FOR PHOLEDS  

UK PubMed Central (United Kingdom)

Novel organic compounds comprising azaborine are provided. In particular, the compounds comprise a dibenzo-1,4,-azaborine core having a phenyl substituent on the boron atom, and aryl or heteroaryl substituents at positions 2 and 6 of the phenyl substituent. These compounds may be advantageously used in organic light-emitting devices to provide improved efficiency and lifetime.

KOTTAS GREGG; KWONG RAYMOND C

332

AZABORININE COMPOUNDS AS HOST MATERIALS AND DOPANTS FOR PHOLEDS  

UK PubMed Central (United Kingdom)

Novel organic compounds comprising azaborine are provided. In particular, the compounds comprise a dibenzo-1,4,-azaborine core having a phenyl substituent on the boron atom, and aryl or heteroaryl substituents at positions 2 and 6 of the phenyl substituent. These compounds may be advantageously used in organic light-emitting devices to provide improved efficiency and lifetime.

KOTTAS GREGG; KWONG RAYMOND C

333

Azaborinine Compounds As Host Materials And Dopants For PHOLEDs  

UK PubMed Central (United Kingdom)

Novel organic compounds comprising azaborine are provided. In particular, the compounds comprise a dibenzo-1,4,-azaborine core having a phenyl substituent on the boron atom, and aryl or heteroaryl substituents at positions 2 and 6 of the phenyl substituent. These compounds may be advantageously used in organic light-emitting devices to provide improved efficiency and lifetime.

KOTTAS GREGG; KWONG RAYMOND C

334

Mechanism-based inactivation of benzo(a)pyrene hydroxylase by aryl acetylenes and aryl olefins  

Energy Technology Data Exchange (ETDEWEB)

A series of aryl acetylenes and aryl olefins have been examined as substrates and inhibitors of cytochrome P-450 dependent monooxgenases in liver microsomes from 5,6-benzoflavone or phenobarbital pretreated rats. 1-Ethynylpyrene, 3-ethynylperylene, 2-ethynylfluorene, methyl 1-pyrenyl acetylene, cis- and trans-1-(2-bromovinyl)pyrene, and 1-allylpyrene serve as mechanism-based irreversible inactivators (suicide inhibitors) of benzo(a)pyrene hydroxylase, while 1-vinylpyrene and phenyl 1-pyrenyl acetylene do not cause a detectable suicide inhibition of benzo(a)pyrene hydroxylase. The mechanism-based loss of benzo(a)pyrene hydroxylase caused by the aryl acetylenes is not accompanied by a corresponding loss of the P-450 content of the microsomes (suicide destruction). The suicide inhibition by these aryl acetylenes therefore does not involve covalent binding to the heme moiety of the monooxygenase. Nevertheless, in the presence of NADPH, /sup 3/H-labeled 1-ethynylpyrene becomes covalently attached to the cytochrome P-450 protein; the measured stoichiometry of binding is one 1-ethynylpyrene per P-450 heme unit. The authors conclude that the inhibition of benzo(a)pyrene hydroxylase produced by 1-ethynylpyrene may be related to the mechanism of suicide inhibition of P-450 activity by chloramphenicol rather than the mechanism of suicide destruction of P-450 previously described for acetylene and propyne.

Gan, L.S.; Lu, J.Y.L.; Alworth, W.L.

1986-05-01

335

Mechanism-based inactivation of benzo[a]pyrene hydroxylase by aryl acetylenes and aryl olefins  

International Nuclear Information System (INIS)

A series of aryl acetylenes and aryl olefins have been examined as substrates and inhibitors of cytochrome P-450 dependent monooxgenases in liver microsomes from 5,6-benzoflavone or phenobarbital pretreated rats. 1-Ethynylpyrene, 3-ethynylperylene, 2-ethynylfluorene, methyl 1-pyrenyl acetylene, cis- and trans-1-(2-bromovinyl)pyrene, and 1-allylpyrene serve as mechanism-based irreversible inactivators (suicide inhibitors) of benzo[a]pyrene hydroxylase, while 1-vinylpyrene and phenyl 1-pyrenyl acetylene do not cause a detectable suicide inhibition of benzo[a]pyrene hydroxylase. The mechanism-based loss of benzo[a]pyrene hydroxylase caused by the aryl acetylenes is not accompanied by a corresponding loss of the P-450 content of the microsomes (suicide destruction). The suicide inhibition by these aryl acetylenes therefore does not involve covalent binding to the heme moiety of the monooxygenase. Nevertheless, in the presence of NADPH, 3H-labeled 1-ethynylpyrene becomes covalently attached to the cytochrome P-450 protein; the measured stoichiometry of binding is one 1-ethynylpyrene per P-450 heme unit. The authors conclude that the inhibition of benzo[a]pyrene hydroxylase produced by 1-ethynylpyrene may be related to the mechanism of suicide inhibition of P-450 activity by chloramphenicol rather than the mechanism of suicide destruction of P-450 previously described for acetylene and propyne

1986-01-01

336

Rhodium(iii)-catalyzed ortho-olefination of aryl phosphonates.  

UK PubMed Central (United Kingdom)

Rhodium(iii)-catalyzed C-H olefination of aryl phosphonic esters is reported for the first time. In this mild and efficient process, the phosphonic ester group is utilized successfully as a new directing group. In addition, mono-olefination for aryl phosphonates is observed using a phosphonic diamide directing group.

Chary BC; Kim S

2013-09-01

337

Regioselective Heck reaction of aliphatic olefins and aryl halides.  

UK PubMed Central (United Kingdom)

A regioselective Heck reaction of aliphatic olefins and aryl bromides is realized at internal carbons of olefins. Methanol solvent promoted halide ionization from neutral arylpalladium halide complexes via hydrogen bonding, so as to create cationic aryl-Pd species for regioselective olefin insertion.

Qin L; Hirao H; Zhou JS

2013-09-01

338

Aryl (meth)acrylates and polymers based on them  

Energy Technology Data Exchange (ETDEWEB)

Data on the synthesis, polymerisation and copolymerisation of aryl (meth)acrylates are generalised and systematised. Chemical and photochemical properties of the polymers and copolymers are considered. Basic directions of practical application of poly[aryl (meth)acrylates] and copolymers are demonstrated. The bibliography includes 449 references.

Syromyatnikov, Vladimir G; Paskal' , Lyudmila P; Savchenko, Irina A [Department of Chemistry, T.G. Shevchenko Kiev National University, Kiev (Ukraine)

1999-09-30

339

Copper-catalyzed arylation of 1H-perfluoroalkanes.  

Science.gov (United States)

A general method has been developed for arylation of readily available 1H-perfluoroalkanes. The method employs aryl iodide and 1H-perfluoroalkane reagents, DMPU solvent, TMP(2)Zn base, and a copper chloride/phenanthroline catalyst. Preliminary mechanistic studies are reported. PMID:21627068

Popov, Ilya; Lindeman, Sergey; Daugulis, Olafs

2011-05-31

340

Copper-catalyzed arylation of 1H-perfluoroalkanes.  

UK PubMed Central (United Kingdom)

A general method has been developed for arylation of readily available 1H-perfluoroalkanes. The method employs aryl iodide and 1H-perfluoroalkane reagents, DMPU solvent, TMP(2)Zn base, and a copper chloride/phenanthroline catalyst. Preliminary mechanistic studies are reported.

Popov I; Lindeman S; Daugulis O

2011-06-01

 
 
 
 
341

Model studies on a synthetically facile series of N-substituted phenyl-N'-pyridin-3-yl ureas leading to 1-(3-pyridylcarbamoyl) indolines that are potent and selective 5-HT(2C/2B) receptor antagonists.  

Digital Repository Infrastructure Vision for European Research (DRIVER)

A model series of 5-HT2C antagonists have been prepared by rapid parallel synthesis. These N-substituted phenyl-N'-pyridin-3-yl ureas were found to have a range of 5-HT2C receptor affinities and selectivities over the closely related 5-HT2A receptor. Extrapolation of simple SAR, derived from this se...

Bromidge, SM; Dabbs, S; Davies, DT; Davies, S; Duckworth, DM; Forbes, IT; Gadre, A; Ham, P; Jones, GE; King, FD; Saunders, DV

342

MICROWAVE ASSISTED SYNTHESIS OF 3-(2-BENZOYL-6-HYDROXY-3-METHYL BENZO[b] FURAN-5-YL)-5-(ARYL)-4, 5-DIHYDRO-1H-PYRAZOLE CARBOTHIOAMIDES AND THEIR ANTIBACTERIAL ACTIVITY Mikrowellen unterstützte Synthese von 3 - (2-Benzoyl-6-HYDROXY-3-METHYL Benzo [b] furan-5-yl) -5 - (ARYL) -4, 5-DIHYDRO-1H-pyrazol CARBOTHIOAMIDES UND ihre antibakterielle Aktivität  

Directory of Open Access Journals (Sweden)

Full Text Available A series of 3-(2-Benzoyl-6-hydroxy-3-methyl benzo[b] furan-5-yl)-5-(aryl)-4, 5-dihydro-1Hpyrazole carbothioamides have been prepared by the reaction of (E)-1-(2-Benzoyl-6-hydroxy-3- methylbenzo[b]furan-5-yl)-3-aryl-2-propen-1-ones with thiosemicarbazide in the presence of sodium hydroxide under microwave irradiation. The structures of newly synthesized compounds have been confirmed on the basis of elemental analysis, IR,1H-NMR,13C-NMR and mass spectral data. All the compounds were screened for their antibacterial activity.

Ashok D, Sudershan K,Khalilullah M

2011-01-01

343

QSAR Studies on N-aryl Derivative Activity Towards Alzheimer’s Disease  

Directory of Open Access Journals (Sweden)

Full Text Available A Quantitative Structure Activity Relationship (QSAR) study has been an attempted on a series of 88 N-aryl derivatives which display varied inhibitory activity towards both acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), targets in Alzheimer’s drug discovery. QSAR models were derived for 53 and 61 compounds for each target, respectively, with the aid of genetic function approximation (GFA) technique using topological, molecular shape, electronic and structural descriptors. The predictive ability of the QSAR model was evaluated using a test set of 26 compounds for AChE (r2pred = 0.857), (q2 = 0.803) and 20 compounds for BChE (r2 pred = 0.882), (q2 = 0.857). The QSAR models point out that AlogP98, Wiener, Kappa-1-AM, Dipole-Mag, and CHI-1 are the important descriptors effectively describing the bioactivity of the compounds.

Kamalakaran Anand Solomon; Srinivasan Sundararajan; Veluchamy Abirami

2009-01-01

344

On solutions of organic strontium compounds  

International Nuclear Information System (INIS)

Preparation of a strontium-organic compound of the type ArSrI (where Ar is the aryl radical) in diethyl ether and benzene with a small addition of tetrahydrofurane (THF), sufficient for the formation of a complex of the composition ArSrIxTHF, is described. The synthesis is carried out in an argon atmosphere. The compounds synthesized react vigorously with atmospheric water and oxygen. The composition of the compounds was confirmed by means of reaction gas chromatography

1978-01-01

345

Application of Ullmann and Ullmann-Finkelstein reactions for the synthesis of N-aryl-N-(1H-pyrazol-3-yl) acetamide or N-(1-aryl-1H-pyrazol-3-yl) acetamide derivatives and pharmacological evaluation.  

UK PubMed Central (United Kingdom)

Ullmann-type reactions are becoming a major tool in medicinal chemistry. In this article, we describe the use of these Copper-catalyzed reactions with various precursors, acyl-heteroarylamines or pyrazoles of interest for pharmacomodulation. To the medicinal chemist they offer new, usually untapped disconnection approaches to compounds of interest. They thus open the way to new original analogues of bioactive compounds possibly not patented, from common building-blocks. They also allow C to N bioisosteric replacements, which sometimes are synthetically challenging. We report for the first time the critical effect of acetylamino substituents on the regioselective arylation of unsymmetrical pyrazoles that are useful for medicinal chemists. Finally, we have applied this strategy to the design of novel AT(1) receptor antagonists. Though this family has been extensively investigated in the past 30 years, N-arylation and C to N replacement made possible by Ullmann chemistry, can produce original antagonists.

Deprez-Poulain R; Cousaert N; Toto P; Willand N; Deprez B

2011-09-01

346

Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives.  

Science.gov (United States)

A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC(50) of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI=23.2 and 3.4, respectively). PMID:18524583

Cheng, Pi; Zhang, Quan; Ma, Yun-Bao; Jiang, Zhi-Yong; Zhang, Xue-Mei; Zhang, Feng-Xue; Chen, Ji-Jun

2008-05-20

347

Palladium-catalyzed decarboxylative arylation of benzoylacrylic acids toward the synthesis of chalcones.  

UK PubMed Central (United Kingdom)

It has been found that readily available 3-benzoylacrylic acids undergo palladium-catalyzed decarboxylative arylation with arylboronic acids in the presence of a copper salt oxidant to produce chalcone derivatives. The decarboxylative arylation could also be achieved using aryl halides as the alternative aryl source to expand the applicable scope.

Unoh Y; Hirano K; Satoh T; Miura M

2013-05-01

348

C- versus O-Arylation of an Enol-Lactone Using Potassium tert-butoxide  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Abstract: The use of potassium tert-butoxide as the base in arylation reactions of an enollactone with a series of benzyl halides was explored. Our work demonstrates that the ratio of C-arylation to O-arylation varies with the substitution pattern of the aryl halide.

Sanae Ibrahimi; Gilles Sauvé; El Moktar Essassi

349

Reversible aryl migrations in metallated ureas: controlled inversion of configuration at a quaternary carbon atom.  

UK PubMed Central (United Kingdom)

Deprotonation with strong bases of N-vinyl ureas carrying an N'-aryl substituent leads to migration of the N'-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents ? to the urea N atom may migrate from C to N.

Tetlow DJ; Vincent MA; Hillier IH; Clayden J

2013-02-01

350

C- versus O-Arylation of an Enol-Lactone Using Potassium tert-butoxide  

Directory of Open Access Journals (Sweden)

Full Text Available Abstract: The use of potassium tert-butoxide as the base in arylation reactions of an enollactone with a series of benzyl halides was explored. Our work demonstrates that the ratio of C-arylation to O-arylation varies with the substitution pattern of the aryl halide.

Sanae Ibrahimi; Gilles Sauvé; El Moktar Essassi

2003-01-01

351

The optical properties, synthesis and characterization of novel 5-aryl-3-benzimidazolyl-1-phenyl-pyrazoline derivatives  

Science.gov (United States)

A series of novel 5-aryl-3-benzimidazolyl-1-phenyl-pyrazoline derivatives were synthesized by the reaction of benzimidazolyl chalcone and phenylhydrazine in 41-72% yields. The compounds were characterized using IR, 1H NMR and HRMS. Absorption and fluorescence spectra were measured in different organic solvent. An intense absorption maxima was noted at ca. 370 nm and emission maxima was noted at ca. 460 nm. The absorption spectra of the pyrazoline derivatives reveal that 5-aryl group attached to the pyrazoline ring hardly influenced the maximum absorption. The fluorescence spectra of these compounds indicated the emission wavelength was red shifted and the fluorescence intensity was decreased with the increase in solvent polarity.

Cao, Xiao Qun; Lin, Xiao Hui; Zhu, Yan; Ge, Yan Qing; Wang, Jian Wu

2012-12-01

352

Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Structural derivatives of 4-MTA, an illegal amphetamine analogue have been previously shown to have anticancer effects in vitro. In this study we report the synthesis of a series of novel 1,3-bis(aryl)-2-nitro-1-propene derivatives related in structure to 4-MTA. A number of these compounds containin...

KNOX, ANDREW; WILLIAMS, DAVID CLIVE; MEEGAN, MARY JANE; CLOONAN, SUZANNE; MCNAMARA, YVONNE

353

Synthesis and biological evaluation of novel C-aryl d-glucofuranosides as sodium-dependent glucose co-transporter 2 inhibitors.  

UK PubMed Central (United Kingdom)

Novel C-aryl-d-glucofuranosides were synthesized and evaluated for their capacity to inhibit human sodium-dependent glucose co-transporter 2 (hSGLT2) and hSGLT1. Compound 21q demonstrated the best in vitro inhibitory activity against SGLT2 in this series (EC50=0.62?M).

Lin TS; Liw YW; Song JS; Hsieh TC; Yeh HW; Hsu LC; Lin CJ; Wu SH; Liang PH

2013-09-01

354

Synthesis and Biological Evaluation of 3-Aryl-quinoxaline-2-carbonitrile 1,4-Di-N-oxide Derivatives as Hypoxic Selective Anti-tumor Agents  

Digital Repository Infrastructure Vision for European Research (DRIVER)

A series of 3-aryl-2-quinoxaline-carbonitrile 1,4-di-N-oxide derivatives were designed, synthesized and evaluated for hypoxic and normoxic cytotoxic activity against human SMMC-7721, K562, KB, A549 and PC-3 cell lines. Many of these new compounds displayed more potent hypoxic cy...

Yunzhen Hu; Qing Xia; Shihao Shangguan; Xiaowen Liu; Yongzhou Hu; Rong Sheng

355

Use of dimethyl carbonate as a solvent greatly enhances the biaryl coupling of aryl iodides and organoboron reagents without adding any transition metal catalysts.  

Science.gov (United States)

The coupling reaction of aryl iodides with arylboronic acids to give biaryl compounds can be efficiently performed without adding a transition metal catalyst. The key to success is the use of dimethyl carbonate as a solvent. This finding provides a new strategy for constructing a biaryl linkage. PMID:22301882

Inamoto, Kiyofumi; Hasegawa, Chisa; Hiroya, Kou; Kondo, Yoshinori; Osako, Takao; Uozumi, Yasuhiro; Doi, Takayuki

2012-02-03

356

Use of dimethyl carbonate as a solvent greatly enhances the biaryl coupling of aryl iodides and organoboron reagents without adding any transition metal catalysts.  

UK PubMed Central (United Kingdom)

The coupling reaction of aryl iodides with arylboronic acids to give biaryl compounds can be efficiently performed without adding a transition metal catalyst. The key to success is the use of dimethyl carbonate as a solvent. This finding provides a new strategy for constructing a biaryl linkage.

Inamoto K; Hasegawa C; Hiroya K; Kondo Y; Osako T; Uozumi Y; Doi T

2012-03-01

357

Synthesis of Novel 1-[(2,6-Dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4-carbaldehydes  

Directory of Open Access Journals (Sweden)

Full Text Available A series of novel 1-[(2,6-dichloro-4-trifluoromethyl)phenyl]-3-aryl-1H-pyrazole-4-carbaldehydes 6a-i were synthesized using the Vilsmeier-Haack reagent. The structures of all the title compounds have been confirmed by elemental analysis, 1H-NMR and 13C-NMR and in addition, the structure of intermediate 5b was investigated by X-ray crystallography.

Huanan Hu; Changhua Ge; Lisheng Ding; Anjiang Zhang

2010-01-01

358

Pd-catalyzed multidehydrogenative cross-coupling between (hetero)arenes and nitroethane to construct ?-aryl nitroethylenes.  

UK PubMed Central (United Kingdom)

The Pd-catalyzed multidehydrogenative cross-coupling reactions of arenes with nitroethane are described. The established methods afford ?-aryl nitroethylenes that are an important class of synthetic intermediates and biologically active compounds in an atom- and step-economical fashion. The reactions were applicable to substituted benzenes and a variety of heterocycles such as benzothiophenes, benzofurans, and indoles. Mechanistic experiments indicated that ?-nitroethylbenzene might be the intermediate in this transformation.

Zhang M; Hu P; Zhou J; Wu G; Huang S; Su W

2013-04-01

359

Laser photolysis of aryl-substituted digermanes. Generation of germyl radicals and germylenes  

Energy Technology Data Exchange (ETDEWEB)

The photochemistry of organosilicon compounds having a /sigma/(Si-Si)-/pi/(C-C) conjugated system has been the subject of considerable interest in recent years. However, there have been few reports on photochemical studies of the germanium analogue. The authors describe herein the first laser photolysis studies on the aryl-substituted digermanes (Ph/sub n/Me/sub 3-n/Ge)/sub 2/ (1-3, n = 1-3, respectively). Photolysis of the phenylated digermanes causes germanium-germanium bond homolysis which leads to the formation of a germyl radical and probably a germylene.

Mochida, Kunio; Wakasa, Masanobu; Nakadaira, Yasuhiro; Sakaguchi, Yoshio; Hayashi, Hisaharu

1988-08-01

360

3-Aryl-4-methyl-2-quinolones targeting multiresistant Staphylococcus aureus bacteria.  

UK PubMed Central (United Kingdom)

The NorA efflux pump lowers intracellular fluoroquinolone concentrations by expelling antibiotics through the membrane of Staphylococcus aureus. We identified 3-aryl-4-methyl-2-quinolin-2-ones as compounds able to restore the activity of the NorA substrate, ciprofloxacin, against resistant S. aureus strains, and acting as efflux pump inhibitors (EPI). In particular, 5-hydroxy-7-methoxy-4-methyl-3-phenylquinolin-2-one (6 c) presents both an EPI and an antimicrobial effect. Its efficacy and safety make it a potential candidate for further investigations.

Doléans-Jordheim A; Veron JB; Fendrich O; Bergeron E; Montagut-Romans A; Wong YS; Furdui B; Freney J; Dumontet C; Boumendjel A

2013-04-01

 
 
 
 
361

Synthesis of aryl alkyl ethers by alkylation of phenols with quaternary ammonium salts.  

Science.gov (United States)

Phenolic compounds can be efficiently O-methylated with tetramethylammonium chloride in diglyme or polyethyleneglycol (PEG) at temperatures of 150-160 °C and in the presence of either K2CO3 or NaOH. When applying benzyltrimethylammonium chloride as a reagent, the benzylation and methylation of phenols occurs, with the benzylation product always predominating. With allyl-substituted phenols as substrates and using NaOH as a base it was possible to achieve both the alkylation and the double-bond isomerization of the allyl group to obtain (E/Z)-propenyl-substituted methyl and benzyl aryl ethers in a single preparative step. PMID:24061652

Maraš, Nenad; Polanc, Slovenko; Ko?evar, Marijan

2010-03-01

362

Synthesis of aryl alkyl ethers by alkylation of phenols with quaternary ammonium salts.  

UK PubMed Central (United Kingdom)

Phenolic compounds can be efficiently O-methylated with tetramethylammonium chloride in diglyme or polyethyleneglycol (PEG) at temperatures of 150-160 °C and in the presence of either K2CO3 or NaOH. When applying benzyltrimethylammonium chloride as a reagent, the benzylation and methylation of phenols occurs, with the benzylation product always predominating. With allyl-substituted phenols as substrates and using NaOH as a base it was possible to achieve both the alkylation and the double-bond isomerization of the allyl group to obtain (E/Z)-propenyl-substituted methyl and benzyl aryl ethers in a single preparative step.

Maraš N; Polanc S; Ko?evar M

2010-03-01

363

Cytotoxic and aryl hydrocarbon hydroxylase-inducing effects of laboratory rodent diets. A cell culture study  

Energy Technology Data Exchange (ETDEWEB)

Extracts of several rodent diets were studied for their cytotoxic and aryl hydrocarbon hydroxylase-inducing properties by an in vitro method. The cell culture system based on a mouse hepatoma cell line (Hepa-1) was shown to be convenient and sensitive method for screening of diets for these parameters implying the presence of compounds potentially harmful in vivo. Considerable differences among diets and batches were detected. Smallest effects were observed with a semipurified diet and with the unrefined diet which - contrary to other four unrefined diets - contained no fish.

Toerroenen, R.; Pelkonen, K.; Kaerenlampi, S. (Univ. of Kuopio (Finland))

1991-01-01

364

PROCESS FOR PRODUCING COMPOUNDS COMPRISING PHENOLIC HYDROXYL GROUPS  

UK PubMed Central (United Kingdom)

Preparation of phenolic hydroxy-substituted compounds (I) comprises desalkylation of alkyl aryl ether compounds (II) with thiourea/aluminum chloride reagent pair. Preparation of phenolic hydroxy-substituted compounds of formula (I) comprises desalkylation of an alkyl aryl ether compounds of formula (II) with thiourea/aluminum chloride reagent pair. R1>1-6C alkyl and either R2>-R6>H, halo, OH, carboxy, nitro, oxo, 1-6C alkylcarbonyl, alkyl, alkoxy or aryl or R2>+R3>5-7 membered ring or fused ring system (optionally substituted with an oxo or unsaturated ring where the fused ring may constitute with the first ring to form a steroid (preferably estratriene derivative optionally substituted with oxo or 1-6C alkylcarbonyloxy group in the 17 position)). [Image

VASS ANDRAS; DUDAS JOZSEF; BORBELY LASZLO; HAASZ FERENC; JEKKEL PETER

365

Ginsenosides are novel naturally-occurring aryl hydrocarbon receptor ligands.  

Science.gov (United States)

The aryl hydrocarbon receptor (AHR) is a ligand-dependent transcription factor that mediates many of the biological and toxicological actions of structurally diverse chemicals. In this study, we examined the ability of a series of ginsenosides extracted from ginseng, a traditional Chinese medicine, to bind to and activate/inhibit the AHR and AHR signal transduction. Utilizing a combination of ligand and DNA binding assays, molecular docking and reporter gene analysis, we demonstrated the ability of selected ginsenosides to directly bind to and activate the guinea pig cytosolic AHR, and to stimulate/inhibit AHR-dependent luciferase gene expression in a recombinant guinea pig cell line. Comparative studies revealed significant species differences in the ability of ginsenosides to stimulate AHR-dependent gene expression in guinea pig, rat, mouse and human cell lines. Not only did selected ginsenosides preferentially activate the AHR from one species and not others, mouse cell line was also significantly less responsive to these chemicals than rat and guinea pig cell lines, but the endogenous gene CYP1A1 could still be inducted in mouse cell line. Overall, the ability of these compounds to stimulate AHR signal transduction demonstrated that these ginsenosides are a new class of naturally occurring AHR agonists. PMID:23776647

Hu, Qin; He, Guochun; Zhao, Jing; Soshilov, Anatoly; Denison, Michael S; Zhang, Aiqian; Yin, Huijun; Fraccalvieri, Domenico; Bonati, Laura; Xie, Qunhui; Zhao, Bin

2013-06-11

366

Ginsenosides are novel naturally-occurring aryl hydrocarbon receptor ligands.  

UK PubMed Central (United Kingdom)

The aryl hydrocarbon receptor (AHR) is a ligand-dependent transcription factor that mediates many of the biological and toxicological actions of structurally diverse chemicals. In this study, we examined the ability of a series of ginsenosides extracted from ginseng, a traditional Chinese medicine, to bind to and activate/inhibit the AHR and AHR signal transduction. Utilizing a combination of ligand and DNA binding assays, molecular docking and reporter gene analysis, we demonstrated the ability of selected ginsenosides to directly bind to and activate the guinea pig cytosolic AHR, and to stimulate/inhibit AHR-dependent luciferase gene expression in a recombinant guinea pig cell line. Comparative studies revealed significant species differences in the ability of ginsenosides to stimulate AHR-dependent gene expression in guinea pig, rat, mouse and human cell lines. Not only did selected ginsenosides preferentially activate the AHR from one species and not others, mouse cell line was also significantly less responsive to these chemicals than rat and guinea pig cell lines, but the endogenous gene CYP1A1 could still be inducted in mouse cell line. Overall, the ability of these compounds to stimulate AHR signal transduction demonstrated that these ginsenosides are a new class of naturally occurring AHR agonists.

Hu Q; He G; Zhao J; Soshilov A; Denison MS; Zhang A; Yin H; Fraccalvieri D; Bonati L; Xie Q; Zhao B

2013-01-01

367

Activity of 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines to Tetrahymena.  

UK PubMed Central (United Kingdom)

A series 6-aryl-pyrrolo[2,3-d]pyrimidine-4-amines (43 compounds), some of which are epidermal growth factor tyrosine kinase inhibitors, were tested for their protozoal toxicity using an environmental Tetrahymena strain as model organism. The protozoacidal activity of the analogues was found to be highly dependent on a 4-hydroxyl group at the 6-aryl ring, and a chiral 1-phenylethanamine substituent in position 4. Further, the potency was affected by the aromatic substitution pattern of the phenylethanamine: the unsubstituted, the meta-fluoro and the para-bromo substituted derivatives had the lowest minimum protozoacidal concentrations (8-16 ?g/mL). Surprisingly, both enantiomers were found to have high potency suggesting that this compound class could have several modes of action. No correlation was found between the compounds protozoacidal activity and the in vitro epidermal growth factor receptor tyrosine kinase inhibitory potency. This suggests that the observed antimicrobial effects are related to other targets. Testing towards a panel of kinases indicated several alternative modes of action.

Kaspersen SJ; Sundby E; Charnock C; Hoff BH

2012-10-01

368

Antioxidant properties of diorganoyl diselenides and ditellurides: modulation by organic aryl or naphthyl moiety.  

UK PubMed Central (United Kingdom)

Diorganoyl dichalcogenide compouds can have antioxidant activity in different in vitro and in vivo models. Here, we have compared the potential antioxidant activity of 1-dinaphthyl diselenide (1-NapSe)(2), 2-dinaphthyl diselenide (2-NapSe)(2), 1-dinaphthyl distelluride (1-NapTe)(2), 2-dinaphthyl ditelluride (2-NapTe)(2) with their well-studied analogs diphenyl diselenide ((PhSe)(2)) and diphenyl telluride ((PhTe)(2)). (PhSe)(2), (PhTe)(2), and naphthalene analogs-inhibited Fe(II)-induced lipid peroxidation, catalytically decomposed hydrogen peroxide and oxidized thiols, such as dithiothreitol (DTT), Cysteine (CYS), dimercaptopropionic acid (DMPS), and thiophenol (PhSH). (PhSe)(2) was the less potent of the tested compounds against Fe(II)-induced lipid peroxidation in brain homogenates and the change in the organic moiety from an aryl to naphthyl group increased considerably the antioxidant potency of diselenide compounds. However, the change from aryl to naphthyl had little effect on the thio-peroxidase-like activity of diorganoyl dichalcogenides. These results suggest that minor changes in the organic moiety of aromatic diselenide compounds can modify profoundly their capacity to inhibit iron-induced lipid peroxidation. The pharmacological properties of organochalcogens are thought to be linked to their capacity of modulating oxidative stress. Consequently, it becomes important to explore the toxicological properties of dinaphthyl diselenides and ditellurides.

Ibrahim M; Hassan W; Meinerz DF; Dos Santos M; V Klimaczewski C; M Deobald A; Costa MS; Nogueira CW; Barbosa NB; Rocha JB

2012-12-01

369

Antioxidant properties of diorganoyl diselenides and ditellurides: modulation by organic aryl or naphthyl moiety.  

Science.gov (United States)

Diorganoyl dichalcogenide compouds can have antioxidant activity in different in vitro and in vivo models. Here, we have compared the potential antioxidant activity of 1-dinaphthyl diselenide (1-NapSe)(2), 2-dinaphthyl diselenide (2-NapSe)(2), 1-dinaphthyl distelluride (1-NapTe)(2), 2-dinaphthyl ditelluride (2-NapTe)(2) with their well-studied analogs diphenyl diselenide ((PhSe)(2)) and diphenyl telluride ((PhTe)(2)). (PhSe)(2), (PhTe)(2), and naphthalene analogs-inhibited Fe(II)-induced lipid peroxidation, catalytically decomposed hydrogen peroxide and oxidized thiols, such as dithiothreitol (DTT), Cysteine (CYS), dimercaptopropionic acid (DMPS), and thiophenol (PhSH). (PhSe)(2) was the less potent of the tested compounds against Fe(II)-induced lipid peroxidation in brain homogenates and the change in the organic moiety from an aryl to naphthyl group increased considerably the antioxidant potency of diselenide compounds. However, the change from aryl to naphthyl had little effect on the thio-peroxidase-like activity of diorganoyl dichalcogenides. These results suggest that minor changes in the organic moiety of aromatic diselenide compounds can modify profoundly their capacity to inhibit iron-induced lipid peroxidation. The pharmacological properties of organochalcogens are thought to be linked to their capacity of modulating oxidative stress. Consequently, it becomes important to explore the toxicological properties of dinaphthyl diselenides and ditellurides. PMID:22983825

Ibrahim, Mohammad; Hassan, Waseem; Meinerz, Daiane Francine; Dos Santos, Matheus; V Klimaczewski, Claudia; M Deobald, Anna; Costa, Maricilia S; Nogueira, Cristina W; Barbosa, Nilda B V; Rocha, Joao B T

2012-09-16

370

Synthesis, Characterization, Anti-Inflammatory and in Vitro Antimicrobial Activity of Some Novel Alkyl/Aryl Substituted Tertiary Alcohols  

Directory of Open Access Journals (Sweden)

Full Text Available The synthesis of some novel alkyl/aryl substituted tertiary alcohols was accomplished in two steps. The synthetic route involves preparation of Grignard reagents by treating alkyl/aryl bromides with magnesium turnings in dry ether. Then substituted chalcones were reacted with the Grignard reagents to afford alkyl/aryl substituted tertiary alcohols 1-10. The structures of the synthesized compounds were assigned on the basis of FT-IR, 1H-NMR, 13C-NMR and mass spectroscopic data. The in vivo anti-inflammatory activity of the synthesized compounds was evaluated using the carrageenan-induced hind paw edema method and was compared with that of ibuprofen. Some of the newly synthesized compounds showed promising anti-inflammatory activity. The tertiary alcohols 1-10 were also screened for antibacterial activity against ten bacterial strains using seven Gram-positive and three Gram-negative bacteria and for antifungal activity against Aspergillus Flavus, Aspergillus Niger and Aspergillus pterus. Tertiary alcohols 1-10 were found to exhibit good to excellent antimicrobial activities compared to levofloxacin and fluconazole used as standard drugs.

Muhammad Baseer; Farzana Latif Ansari; Zaman Ashraf; Rafiuzzaman SaeedulHaq

2011-01-01

371

Formation of self-assembled monolayers of ?-conjugated molecules on TiO2 surfaces by thermal grafting of aryl and benzyl halides.  

UK PubMed Central (United Kingdom)

We demonstrate the formation of molecular monolayers of ?-conjugated organic molecules on nanocrystalline TiO(2) surfaces through the thermal grafting of benzyl and aryl halides. X-ray photoelectron spectroscopy and Fourier-transform infrared spectroscopy were used to characterize the reactivity of aryl and benzyl chlorides, bromides, and iodides with TiO(2) surfaces, along with controls consisting of nonhalogenated compounds. Our results show that benzyl and aryl halides follow a similar reactivity trend (I > Br > Cl >> H). While the ability to graft benzyl halides is consistent with the well-known Williamson ether synthesis, the grafting of aryl halides has no similar precedent. The unique reactivity of the TiO(2) surface is demonstrated using nuclear magnetic resonance spectroscopy to compare the surface reactions with the liquid-phase interactions of benzyl and aryl iodides with tert-butanol and -butoxide anion. While the aryl iodides show no detectable reactivity with a tert-butanol/tert-butoxide mixture, they react with TiO(2) within 2 h at 50 °C. Atomic force microscopy studies show that grafting of 4-iodo-1-(trifluoromethyl)benzene onto the rutile TiO(2)(110) surface leads to a very uniform, homogeneous molecular layer with a thickness of ?0.45 nm, demonstrating formation of a self-terminating molecular monolayer. Thermal grafting of aryl iodides provides a facile route to link ?-conjugated molecules to TiO(2) surfaces with the shortest possible linkage between the conjugated electron system and the TiO(2).

English CR; Bishop LM; Chen J; Hamers RJ

2012-05-01

372

Cloning, expression and characterization of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium strain BKM-F-1767  

Directory of Open Access Journals (Sweden)

Full Text Available Abstract Background The white-rot fungus Phanerochaete chrysosporium is among the small group of fungi that can degrade lignin to carbon dioxide while leaving the crystalline cellulose untouched. The efficient lignin oxidation system of this fungus requires cyclic redox reactions involving the reduction of aryl-aldehydes to the corresponding alcohols by aryl-alcohol dehydrogenase. However, the biochemical properties of this enzyme have not been extensively studied. These are of most interest for the design of metabolic engineering/synthetic biology strategies in the field of biotechnological applications of this enzyme. Results We report here the cloning of an aryl-alcohol dehydrogenase cDNA from the white-rot fungus Phanerochaete chrysosporium, its expression in Escherichia coli and the biochemical characterization of the encoded GST and His6 tagged protein. The purified recombinant enzyme showed optimal activity at 37°C and at pH 6.4 for the reduction of aryl- and linear aldehydes with NADPH as coenzyme. NADH could also be the electron donor, while having a higher Km (220 ?M) compared to that of NADPH (39 ?M). The purified recombinant enzyme was found to be active in the reduction of more than 20 different aryl- and linear aldehydes showing highest specificity for mono- and dimethoxylated Benzaldehyde at positions 3, 4, 3,4 and 3,5. The enzyme was also capable of oxidizing aryl-alcohols with NADP?+?at 30°C and an optimum pH of 10.3 but with 15 to 100-fold lower catalytic efficiency than for the reduction reaction. Conclusions In this work, we have characterized the biochemical properties of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium. We show that this enzyme functions in the reductive sense under physiological conditions and that it displays relatively large substrate specificity with highest activity towards the natural compound Veratraldehyde.

Yang Dong-Dong; François Jean; de Billerbeck Gustavo M

2012-01-01

373

Cloning, expression and characterization of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium strain BKM-F-1767.  

UK PubMed Central (United Kingdom)

BACKGROUND: The white-rot fungus Phanerochaete chrysosporium is among the small group of fungi that can degrade lignin to carbon dioxide while leaving the crystalline cellulose untouched. The efficient lignin oxidation system of this fungus requires cyclic redox reactions involving the reduction of aryl-aldehydes to the corresponding alcohols by aryl-alcohol dehydrogenase. However, the biochemical properties of this enzyme have not been extensively studied. These are of most interest for the design of metabolic engineering/synthetic biology strategies in the field of biotechnological applications of this enzyme. RESULTS: We report here the cloning of an aryl-alcohol dehydrogenase cDNA from the white-rot fungus Phanerochaete chrysosporium, its expression in Escherichia coli and the biochemical characterization of the encoded GST and His6 tagged protein. The purified recombinant enzyme showed optimal activity at 37°C and at pH 6.4 for the reduction of aryl- and linear aldehydes with NADPH as coenzyme. NADH could also be the electron donor, while having a higher Km (220 ?M) compared to that of NADPH (39 ?M). The purified recombinant enzyme was found to be active in the reduction of more than 20 different aryl- and linear aldehydes showing highest specificity for mono- and dimethoxylated Benzaldehyde at positions 3, 4, 3,4 and 3,5. The enzyme was also capable of oxidizing aryl-alcohols with NADP(+) at 30°C and an optimum pH of 10.3 but with 15 to 100-fold lower catalytic efficiency than for the reduction reaction. CONCLUSIONS: In this work, we have characterized the biochemical properties of an aryl-alcohol dehydrogenase from the white-rot fungus Phanerochaete chrysosporium. We show that this enzyme functions in the reductive sense under physiological conditions and that it displays relatively large substrate specificity with highest activity towards the natural compound Veratraldehyde.

Yang DD; François JM; de Billerbeck GM

2012-01-01

374

Palladium-catalyzed amination of aryl halides on solid support.  

UK PubMed Central (United Kingdom)

[reaction: see text] The first examples of the Pd(0)-catalyzed amination of aryl halides using Rink-resins as nitrogen source are described. Pd(2)dba(3)/BINAP/NaO-t-Bu was found to be the most efficient catalyst/base system, while a solvent mixture of dioxane and tert-butyl alcohol was shown to enhance the selectivity toward the desired monoarylation. Moderate to good yields and excellent purities of the amination products were found with electron-poor aryl halides, while electon-rich aryl halides failed to react under these conditions.

Weigand K; Pelka S

2002-12-01

375

Palladium-catalyzed amination of aryl halides on solid support.  

Science.gov (United States)

[reaction: see text] The first examples of the Pd(0)-catalyzed amination of aryl halides using Rink-resins as nitrogen source are described. Pd(2)dba(3)/BINAP/NaO-t-Bu was found to be the most efficient catalyst/base system, while a solvent mixture of dioxane and tert-butyl alcohol was shown to enhance the selectivity toward the desired monoarylation. Moderate to good yields and excellent purities of the amination products were found with electron-poor aryl halides, while electon-rich aryl halides failed to react under these conditions. PMID:12489962

Weigand, Klaus; Pelka, Sylvie

2002-12-26

376

Boronated porphyrin compounds  

Energy Technology Data Exchange (ETDEWEB)

A compound is described having the structure ##STR1## where R preferably is ##STR2## and most preferably R.sup.3 is a closo-carborane and R.sup.2 is --H, an alkyl or aryl having 1 to about 7 carbon atoms, This invention was made with Government support under NIH Grant No. CA-37961 awarded by the Department of Health and Human Services and under the Associated Universities Inc. Contract No. De-AC02-76CH00016 with the U.S. Department of Energy. The Government has rights in this invention.

Kahl, Stephen B. (Portola Valley, CA); Koo, Myoung-Seo (San Francisco, CA)

1992-01-01

377

Indium-catalyzed annulation of 3-aryl- and 3-heteroarylindoles with propargyl ethers: synthesis and photoluminescent properties of aryl- and heteroaryl[c]carbazoles.  

Science.gov (United States)

Treatment of 3-aryl- and 3-heteroarylindoles with propargyl ethers under indium catalysis successfully provided aryl- and heteroaryl[c]carbazoles, which were found to be more efficient emitters compared with the corresponding [a]-analogs. PMID:23354490

Nagase, Yuta; Shirai, Hiroyuki; Kaneko, Masayoshi; Shirakawa, Eiji; Tsuchimoto, Teruhisa

2013-03-01

378

Indium-catalyzed annulation of 3-aryl- and 3-heteroarylindoles with propargyl ethers: synthesis and photoluminescent properties of aryl- and heteroaryl[c]carbazoles.  

UK PubMed Central (United Kingdom)

Treatment of 3-aryl- and 3-heteroarylindoles with propargyl ethers under indium catalysis successfully provided aryl- and heteroaryl[c]carbazoles, which were found to be more efficient emitters compared with the corresponding [a]-analogs.

Nagase Y; Shirai H; Kaneko M; Shirakawa E; Tsuchimoto T

2013-03-01

379

Compounds of thiourea and its complexes with metal salts  

International Nuclear Information System (INIS)

A review of literature on thiourea compounds is given. Three types of the compounds are described: clathrates, ion complexes and coordination compounds. The main attention is paid to thiourea complexes of transition metals. The structure of the complexes is considered, using X-ray structural analysis and other physicochemical methods. Stability and lability of thiourea coordination compounds and its N- and N, N'-substituted derivatives are characterized, as well as peculiarities of the given ligands in substitution reactions. Acid-basic, redox and thermal properties of thioamide complexes are discussed.

1985-01-01

380

Aryl hydrocarbon receptor control of adaptive immunity.  

UK PubMed Central (United Kingdom)

The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that belongs to the family of basic helix-loop-helix transcription factors. Although the AhR was initially recognized as the receptor mediating the pathologic effects of dioxins and other pollutants, the activation of AhR by endogenous and environmental factors has important physiologic effects, including the regulation of the immune response. Thus, the AhR provides a molecular pathway through which environmental factors modulate the immune response in health and disease. In this review, we discuss the role of AhR in the regulation of the immune response, the source and chemical nature of AhR ligands, factors controlling production and degradation of AhR ligands, and the potential to target the AhR for therapeutic immunomodulation.

Quintana FJ; Sherr DH

2013-01-01

 
 
 
 
381

Efficient synthesis of N-2-aryl-1,2,3-triazole fluorophores via post-triazole arylation.  

UK PubMed Central (United Kingdom)

Efficient post-triazole regioselective N-2 arylation was developed from C-4, C-5 disubstituted-1,2,3-NH-triazoles. Three different approaches had been investigated, including S(N)Ar, Cu(I) catalyzed aryl amidation and Cu(II) mediated boronic acid coupling. The N-2-aryl triazoles were successfully synthesized with excellent yields. The structures were characterized by X-ray crystallography and some N-2-triazole products gave strong fluorescence with various emission controlled by the C-5 groups.

Liu Y; Yan W; Chen Y; Petersen JL; Shi X

2008-12-01

382

Synthesis Of [2h, 13c]M [2h2m 13c], And [2h3,, 13c] Methyl Aryl Sulfones And Sulfoxides  

Energy Technology Data Exchange (ETDEWEB)

The present invention is directed to labeled compounds, [.sup.2 H.sub.1, .sup.13 C], [.sup.2 H.sub.2, .sup.13 C] and [.sup.2 H.sub.3, .sup.13 C]methyl aryl sulfones and [.sup.2 H.sub.1, .sup.13 C], [.sup.2 H.sub.2, .sup.13 C] and [.sup.2 H.sub.3, .sup.13 C]methyl aryl sulfoxides, wherein the .sup.13 C methyl group attached to the sulfur of the sulfone or sulfoxide includes exactly one, two or three deuterium atoms and the aryl group is selected from the group consisting of 1-naphthyl, substituted 1-naphthyl, 2-naphthyl, substituted 2-naphthyl, and phenyl groups with the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently, hydrogen, a C.sub.1 -C.sub.4 lower alkyl, a halogen, an amino group from the group consisting of NH.sub.2, NHR and NRR' where R and R' are each a C.sub.1 -C.sub.4 lower alkyl, a phenyl, or an alkoxy group. The present invention is also directed to processes of preparing methyl aryl sulfones and methyl aryl sulfoxides.

Martinez, Rodolfo A. (Santa Fe, NM); Alvarez, Marc A. (Santa Fe, NM); Silks, III, Louis A. (Los Alamos, NM); Unkefer, Clifford J. (Los Alamos, NM); Schmidt, Jurgen G. (Los Alamos, NM)

2004-07-20

383

Discovery of 2-aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-ones as novel EGFR inhibitor by scaffold hopping.  

Science.gov (United States)

2-Aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-one has been proposed as a novel scaffold of EGFR inhibitor based on scaffold hoping. In the present study, a series of 2-aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-one derivatives were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against two human cancer cell lines, including A431 and A549. The SAR of the title compounds was preliminarily discussed. The compounds with ideal inhibition were evaluated through ELISA-based EGFR-TK assay. Compound 6c showed the best activity against A431 and EGFR tyrosine kinase. These findings suggest that title compounds are EGFR inhibitors with novel structures. PMID:24094432

Kang, Bo-Rui; Shan, Ai-Lin; Li, Yi-Ping; Xu, Jing; Lu, She-Min; Zhang, San-Qi

2013-09-18

384

Discovery of 2-aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-ones as novel EGFR inhibitor by scaffold hopping.  

UK PubMed Central (United Kingdom)

2-Aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-one has been proposed as a novel scaffold of EGFR inhibitor based on scaffold hoping. In the present study, a series of 2-aryl-8-hydroxy (or methoxy)-isoquinolin-1(2H)-one derivatives were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against two human cancer cell lines, including A431 and A549. The SAR of the title compounds was preliminarily discussed. The compounds with ideal inhibition were evaluated through ELISA-based EGFR-TK assay. Compound 6c showed the best activity against A431 and EGFR tyrosine kinase. These findings suggest that title compounds are EGFR inhibitors with novel structures.

Kang BR; Shan AL; Li YP; Xu J; Lu SM; Zhang SQ

2013-09-01

385

Azo-hydrazone tautomerism of aryl azo pyridone dyes  

Directory of Open Access Journals (Sweden)

Full Text Available In the last three or four decades disperse dyes derived from pyridones (in particular azo pyridone dyes) have gained in importance, and are widely used in various fields. These compounds have excellent coloration properties, and are suitable for the dyeing of polyester fabrics. Basic features of these dyes are simplicity of their synthesis by diazotation and azo coupling. They generally have high molar extinction coefficient with medium to high light and wet fastness. The absorption maxima of these dyes show their visible absorption wavelength ranging from yellow to orange, which can be attributed to poorly delocalized electrons in the pyridone ring. However, there are several dyes with deep colors such as red or violet. Pyridone dyes with alkyl and aryl groups in ortho position to azo group show 2-pyridone/2-hydroxypyridine tautomerism, while those containing OH and NHR groups conjugated with the azo group show azo-hydrazone tautomerism. Determining azo-hydrazone tautomerism could be therefore interesting, since the tautomers have different physico-chemical properties and most importantly different coloration. The literature on azo-hydrazone tautomerism, determination of equilibrium position, and investigation of substituent and solvent influence on tautomerism has been summarized in the presented review. The general conclusion is that the equilibrium between two tautomers is influenced by the structure of the compounds and by the solvents used. The tautomeric behavior patterns of the arylazo pyridone dyes in the reviewed literature has been studied using various instrumental techniques, including FT-IR, UV-vis, and NMR spectroscopy. The quantum chemical calculations related to the azo-hydrazon tautomerism have also been included. A large number of pyridone dyes exist in hydrazone form in solid state, while in solvents there is a mixture of tautomers. In addition, the X-ray single-crystal diffraction data analysis of some commercial pyridone dyes has been discussed concluding that they all crystallize in the hydrazone form.

Mirkovi? Jelena M.; Uš?umli? Gordana S.; Marinkovi? Aleksandar D.; Mijin Dušan Ž.

2013-01-01

386

Docking of oxalyl aryl amino benzoic acid derivatives into PTP1B  

Directory of Open Access Journals (Sweden)

Full Text Available Protein Tyrosine Phosphatases (PTPs) that function as negative regulators of the insulin signaling cascade have been identified as novel targets for the therapeutic enhancement of insulin action in insulin resistant disease states. Reducing Protein Tyrosine Phosphatase1B (PTP1B) abundance not only enhances insulin sensitivity and improves glucose metabolism but also protects against obesity induced by high fat feeding. PTP1B inhibitors such as Formylchromone derivatives, 1, 2-Naphthoquinone derivatives and Oxalyl aryl amino benzoic derivatives may eventually find an important clinical role as insulin sensitizers in the management of Type-II Diabetes and metabolic syndrome. We have carried out docking of modified oxalyl aryl amino benzoic acid derivatives into three dimensional structure of PTP1B using BioMed CAChe 6.1. These compounds exhibit good selectivity for PTP1B over most of phosphatases in selectivity panel such as SHP-2, LAR, CD45 and TCPTP found in literature. This series of compounds identified the amino acid residues such as Gly220 and Arg221 are important for achieving specificity via H-bonding interactions. Lipophilic side chain of methionine in modified oxalyl aryl amino benzoic acid derivative [1b (a2, b2, c1, d)] lies in closer vicinity of hydrophobic region of protein consisted of Meth258 and Phe52 in comparison to active ligand. Docking Score in [1b (a2, b2, c1, d)] is -131.740Kcal/mol much better than active ligand score -98.584Kcal/mol. This information can be exploited to design PTP1B specific inhibitors.

Neelam Verma; Minakshi Mittal; Raman kumar Verma

2008-01-01

387

Direct stereospecific amination of alkyl and aryl pinacol boronates.  

Science.gov (United States)

The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate. PMID:23002712

Mlynarski, Scott N; Karns, Alexander S; Morken, James P

2012-09-24

388

Palladium-catalyzed arylation of simple arenes with iodonium salts.  

UK PubMed Central (United Kingdom)

The development of an arylation protocol for simple arenes with diaryliodonium salts using the Herrmann-Beller palladacycle catalyst is reported. The reaction takes simple aromatic feedstocks and creates valuable biaryls for use in all sectors of the chemical industry.

Storr TE; Greaney MF

2013-03-01

389

C-ARYL GLUCOSIDE SGLT2 INHIBITORS AND METHOD  

UK PubMed Central (United Kingdom)

C-aryl glucosides which are inhibitors of sodium dependent glucose transporters found in the intestine and kidney (SGLT2), shown as formula I, a pharmaceutical composition and pharmaceutical combination.

HU SHAOJING; LONG WEI; SHEN XIAOYAN; TAN FENLAI; WANG YINXIANG

390

Aryl C-glycosylation of phenols with glycosyl trifluoroacetimidates  

Digital Repository Infrastructure Vision for European Research (DRIVER)

Aryl C-glycosylation of a variety of phenols with glycosyl trifluoroacetimidates in the presence of TMSOTf was examined, leading to the corresponding ortho-hydroxyaryl C-glycosides in variable yields. © 2006 Elsevier Ltd. All rights reserved.

Li, Y; Wei, G; Yu, B

391

Heterocyclic compounds  

UK PubMed Central (United Kingdom)

A compound of the formula (I) or an acid addition salt thereof, wherein R is hydrogen or C1-4 alkyl, R1 is chlorine or methyl optionally substituted by one or two fluorine, R2a to R2d are the same or different and are chosen from the group comprising hydrogen, chlorine, bromine, fluorine, C1-4 alkyl optionally substituted by fluorine or chlorine atoms, C1-4 alkoxy, C1-4 acyl, C1-4 alkoxycarbonyl, C1-4alkylthio, nitro, cyano, amino optionally substituted by C1-4 alkyl or C1-4 acyl; E is C6-10 aryl or aralkyl, a group CH2C (Me)2OR3 wherein R3 is hydrogen, C1-4 acyl, C1-4 alkyl or C2-8 carbamyl, a group CH=C(Me)CH2CH2CH=CMe2, a group - Me2, a group OCHR4R5 wherein R4and R5 are the same or different and each is methyl or ethyl, a group CH=CR6R7 wherein R6 is hydrogen, chlorine, bromine, fluorine, C1-4 alkyl, C1-8 alkoxycarbonyl, C1-4 alkynyl or C1-8 acyl and R7 is hydrogen, chlorine, bromine, fluorine or C1-4 alkyl, or a group CH=X-Y-R8 wherein X is N or C(R9) wherein R9 is hydrogen or C1-6alkyl, Y is oxygen, sulphur or a group NR10 wherein R10 is C1-8 hydrocarbyl, R8 is C1-4 acyl or C1-10 hydrocarbyl optionally substituted by C1-4 alkyl, C1-4 alkoxy, C1-4 acyl or halogen, or, when X is nitrogen, R8 may be hydrogen; provided that at least of of R2a to R2d is other than hydrogen when R1 is methyl or chlorine except when E is OCHR4R5, C6-10 aryl and aralkyl, CH=CR6R7 or CH=XYR8 or R3 is C2-8 carbamyl and that R2c is not methyl when R1 is methyl except when E is CH=CR6R7 or CH=XYR8, and other than 1-geranyl-2-methylbenzimidazole, processes for their preparation, formulations containing them and their use in the control of pests, helminths and fungi.

Weston John Bernard; Pulman David Allen; Frenkel Alexander David

392

Design and synthesis of N-alkyl-N'-substituted 2,4-dioxo-3,4-dihydropyrimidin-1-diacylhydrazine derivatives as ecdysone receptor agonist.  

UK PubMed Central (United Kingdom)

Based on the discovery of thymine as an ecdysteroid agonist, a series of 1,4-disubstituted diacylhydrazine derivatives with a thymine moiety were designed and synthesized. The activities of these compounds against Spodoptera litura (Fabricius) were evaluated by the insect immersion method. Results showed that compound 2h with an N-cyclohexylmethyl substituent exhibits the most potent agonist activity with a median lethal concentration of 23.21 ?g/mL. This compound also caused malformation of molting larvae and adults. Compound 2 h was further demonstrated as an ecdysteroid agonist by reporter gene assay on the Spodoptera frugiperda cell line (Sf9 cells). A molecular docking study indicated that hydrophobic interactions and the formation of hydrogen bonds between the compounds and the ecdysone receptor play critical roles in promoting the binding affinity of the compound. The structure of compound 2h may serve as a favorable template for the development of new ecdysteroid agonists with a pyrimidinedione moiety.

Liu X; Zhang L; Tan JG; Xu HH

2013-08-01

393

Selective copper catalysed aromatic N-arylation in water  

DEFF Research Database (Denmark)

4,7-Dipyrrolidinyl-1,10-phenanthroline (DPPhen) was identified as an efficient ligand for copper catalyzed selective arom. N-arylation in water. N-Arylation of indoles, imidazoles and purines proceeds with moderate to excellent yields and complete selectivity over aliph. amines. Aq. medium and the possibility for low metal and ligand loadings give the process a benign environmental profile. [on SciFinder(R)

Engel-Andreasen, Jens; Shimpukade, Bharat

2013-01-01

394

Palladium-catalyzed intermolecular coupling of aryl halides and amides.  

UK PubMed Central (United Kingdom)

[formula: see text] The first general intermolecular C-N bond-forming reactions between aryl halides and amides were realized using a palladium catalyst with Xantphos as the ligand. Aryl triflates, carbamates, and sulfonamides are also viable substrates for the amidations, which proceed at 45-110 degrees C with 1-4 mol% of Pd catalyst in 66-99% yields and exhibit good functional group compatibility.

Yin J; Buchwald SL

2000-04-01

395

Novel 2-aryl-naphtho[1,2-d]oxazole derivatives as potential PTP-1B inhibitors showing antihyperglycemic activities.  

UK PubMed Central (United Kingdom)

A series of 2-aryl-naphtho[1,2-d]oxazole derivatives have been synthesized and evaluated for PTP-1B inhibitory activity. The compounds have been screened in vivo for antidiabetic activity under sucrose loaded model (SLM), sucrose-challenged streptozotocin-induced diabetic rat model (STZ-S) and db/db mice model. Compounds 8 and 12 have shown promising PTP-1B inhibitory activity, significant antidiabetic activity, moderate lipid and triglyceride lowering activity.

Kumar A; Ahmad P; Maurya RA; Singh AB; Srivastava AK

2009-01-01

396

Palladium-mediated arylation of 3-aminopiperidines and 3-aminopyrrolidines.  

Science.gov (United States)

This paper describes the palladium-catalyzed arylation of 1-substituted 3-aminopyrrolidines or piperidines. Palladium(0) (1-2 mol %) in conjunction with "Buchwald's ligand" [2-(dimethylamino)-2'-(dicyclohexylphosphine)biphenyl] was shown to be the catalyst of choice for the coupling with aryl bromides or chlorides. When bromobenzene was used, a strong temperature effect was noticed. Whereas no reaction occurred at 100 degrees C, yields higher than 85% were obtained at 130 degrees C for each substrate. Such an effect was not observed when diphosphines were used. Whereas Xantphos and, to a lesser extent BINAP, were moderately efficient in the coupling of all diamines, the palladium-mediated arylation in the presence of monophosphines was strongly dependent on the substrate. The results suggest the participation of both nitrogens of the aminoheterocycle in the reactive intermediate. This participation could also account for the highly selective arylation of the endocyclic nitrogen of unsubstituted 3-aminopyrrolidine or piperidine. Optimal conditions were found for the arylation using 2- or 4-substituted electron-poor or enriched aryl halides. PMID:15575771

Jean, Ludovic; Rouden, Jacques; Maddaluno, Jacques; Lasne, Marie-Claire

2004-12-10

397

A convenient catalyst system for microwave accelerated cross-coupling of a range of aryl boronic acids with aryl chlorides  

Directory of Open Access Journals (Sweden)

Full Text Available Abstract A convenient microwave accelerated cross-coupling procedure between aryl chlorides with a range of boronic acids has been developed. An explanation for the low reactivity of highly fluorinated boronic acids in Suzuki coupling is provided.

Clarke Matthew L; France Marcia B; Fuentes Jose A; Milton Edward J; Roff Geoffrey J

2007-01-01

398

CONJUGATED AROMATIC COMPOUND, OPTICAL MATERIAL, AND OPTICAL ELEMENT  

UK PubMed Central (United Kingdom)

The present invention relates to a conjugated aromatic compound represented by the Formula (1) in claim 1 (in the formula, Ar1 represents a hydrogen atom or an aryl group optionally having a substituent Ar2 and Ar3 each represent a hydrogen atom or an aryl group optionally having a substituent but at least one of Ar2 and Ar3 represents an aryl group optionally having a substituent and A represents an aromatic hydrocarbon group) and relates to an optical material containing the conjugated aromatic compound. The conjugated aromatic compound and the optical material have characteristics of a high chromatic aberration correction function, high refractive-index dispersion characteristics (Abbe number ( d)) and high secondary dispersion characteristics ( g,F) (anomalous dispersion characteristics).

SAITOH TERUNOBU

399

Palladium-catalyzed unsymmetrical aryl couplings in sequence leading to o-teraryls: dramatic olefin effect on selectivity.  

UK PubMed Central (United Kingdom)

Selectively substituted o-teraryls are obtained by palladium/norbornene-catalyzed reaction of aryl iodides, aryl bromides and aryl boronic acids in ordered sequence; high selectivity is attained thanks to the addition of diethyl maleate acting as palladium ligand.

Motti E; Della Ca' N; Deledda S; Fava E; Panciroli F; Catellani M

2010-06-01

400

Method for manufacturing aromatic compounds  

UK PubMed Central (United Kingdom)

Preparing (hetero)aromatic compounds (I) comprises reacting (hetero)aromatic boron compounds (II) with aromatic compounds (III) under the use of a solvent and in the presence of a base, where the solvent is a low-water-polar solvent and the base is a borate. Preparing (hetero)aromatic compounds of formula (Ar1-Ar2) (I) comprises reacting (hetero)aromatic boron compounds of formula (Ar1-B(Z1)-Z2) (II) with aromatic compounds of formula (Ar2-Y1) (III) under the use of a solvent in the presence of a base, where the solvent is a low-water-polar solvent and the base is a borate. Ar1, Ar2 : optionally substituted (hetero)aryl either Z1, Z2 : hydroxy, dialkylamino, 1-15C-alkyloxy or 6-15C-aryloxy or Z1+Z2 : a ring system and Y1 : halo or pseudohalo.

CEZANNE CARINA; WEKWERT VOLKER

 
 
 
 
401

Selective antagonists at group I metabotropic glutamate receptors: synthesis and molecular pharmacology of 4-aryl-3-isoxazolol amino acids  

DEFF Research Database (Denmark)

Homologation of (S)-glutamic acid (Glu, 1) and Glu analogues has previously provided ligands with activity at metabotropic Glu receptors (mGluRs). The homologue of ibotenic acid (7), 2-amino-3-(3-hydroxy-5-isoxazolyl)propionic acid (HIBO, 8), and the 4-phenyl derivative of 8, compound 9a, are both antagonists at group I mGluRs. Here we report the synthesis and molecular pharmacology of HIBO analogues 9b-h containing different 4-aryl substituents. All of these compounds possess antagonist activity at group I mGluRs but are inactive at group II and III mGluRs.

Kromann, Hasse; SlØk, Frank A

2002-01-01

402

A site selective C-H arylation of free-(NH2) adenines with aryl chlorides: application to the synthesis of 6,8-disubstituted adenines.  

UK PubMed Central (United Kingdom)

An efficient site selective method for the direct arylation of free-(NH2) adenines 1 to provide a range of C-8 arylated adenines 3 in excellent yields is described. This process based on the use of Pd(OH)2/C as the catalyst and a stoichiometric amount of CuI under ligandless conditions is general. It allows the coupling to proceed with a variety of aryl halides, including for the first time cheaper and less reactive aryl chlorides. The extension of this process for the sequential preparation of non-symmetrical C8/N6-arylated adenines 4 is also reported.

Sahnoun S; Messaoudi S; Brion JD; Alami M

2009-10-01

403

Comparison of Diffusion Coefficients of Aryl Carbonyls and Aryl Alcohols in Hydroxylic Solvents. Evidence that the Diffusion of Ketyl Radicals in Hydrogen-Bonding Solvents is Not Anomalous?  

Energy Technology Data Exchange (ETDEWEB)

The diffusion coefficients of a benzyl-, sec-phenethyl-, and diphenylmethyl alcohol and the corresponding aryl carbonyls (benzaldehyde, acetophenone and benzophenone) were measured by Taylor's dispersion method in both ethyl and isopropyl alcohol. The experimental values are compared to published transient grating measurements of the corresponding aryl ketyl radicals (benzyl-, sec-phenethyl-, and diphenylmethyl-ketyl radical). In general, the diffusion coefficient of the aryl alcohols and the corresponding aryl ketyl radicals are equivalent within experimental error. This work shows that the diffusion of ketyl radicals is not anomalously slow and that aryl alcohols are significantly better models than the corresponding aryl ketones for analyzing the diffusion of aryl ketyl radicals in both ethyl and isopropyl alcohol. Empirical estimates of the diffusion coefficients of aryl alcohols using the Spernol-Wirtz and Wilke-Chang modifications to the Stokes-Einstein diffusion equation do not adequately account for the interactions between the aryl ketyl radicals or aryl alcohols with the hydroxylic solvents ethyl and isopropyl alcohol. The excellent agreement between the experimental diffusion coefficients of the aryl alcohols and the corresponding ketyl radicals show that the transient grating method can provide accurate estimates for the diffusion coefficients of transient species. This is especially important when a stable model is not available, for example the pyranyl radical.

Autrey, S Thomas (BATTELLE (PACIFIC NW LAB)); Camaioni, Donald M.(BATTELLE (PACIFIC NW LAB)); Kandanarachchi, Pramod H.(ASSOC WESTERN UNIVERSITY); Franz, James A.(BATTELLE (PACIFIC NW LAB))

2000-12-01

404

Easy activation of the aryl-sulfur bond by platinum(II).  

UK PubMed Central (United Kingdom)

The reagents 1,2-C6H4(CH=NR)(SMe), R = CH2CH2NMe2 or Ph, react with [Pt2Me4(?-SMe2)2] by oxidative addition of the aryl-sulfur bond to give the corresponding crystalline binuclear platinum(IV) compounds [Pt2Me4(?-SMe)2(?(2)-C,N-C6H4-2-CH=NR)2], as the isomers with Ci (R = CH2CH2NMe2 or Ph) or C1 (R = Ph) symmetry. These first examples of C-S bond activation at platinum(II) occur easily at room temperature, and the reactions give complex equilibria of isomeric products, from which the isolated compounds crystallise.

Kim S; Boyle PD; McCready MS; Pellarin KR; Puddephatt RJ

2013-07-01

405

C-aryl glucoside SGLT2 inhibitors and method for their production  

UK PubMed Central (United Kingdom)

Disclosed is a C-aryl glucoside as represented by formula I. Further disclosed is a pharmaceutical composition comprising the above compound and a pharmaceutically acceptable carrier therefor or a pharmaceutical combination comprising the above compound and at least one therapeutic agent selected from the group consisting of antidiabetic agents (such as metformin, glyburide, glimepiride, glipyride, glipizide, chlorpropamide, gliclazide, acarbose, miglitol, pioglitazone, troglitazone, rosiglitazone, insulin, isaglitazone, repaglinide, nateglinide, muraglitizar or peliglitazar), anti-obesity agents (such as rimonabant, orlistat, sibutramine, topiramate, dexamphetamine, phentermine, phenylpropanolamine or mazindol), anti-hypertensive agents, anti-atherosclerotic agents or lipid-lowering agents (such as pravastatin, lovastatin, simvastatin, atorvastatin, cerivastatin, fluvastatin, nisvastatin, visastatin, atavastatin, rosuvastatin, fenofibrate, gernfibrozil, clofibrate or avasimibe).

WASHBURN WILLIAM; MENG WEI

406

Palladium-catalyzed direct N-arylation of nucleosides, nucleotides, and oligonucleotides for efficient preparation of dG-N2 adducts with carcinogenic amino-/nitroarenes.  

Science.gov (United States)

A method for direct palladium-catalyzed N-arylation reaction of nucleobases was developed for the convenient synthesis of DNA adducts with carcinogenic compounds. Using xantphos as the phosphine ligand and tetraethylammonium fluoride as the base in DMSO, several o-iodonitroarenes could be efficiently coupled with 2'-deoxyguanosine, 2'-deoxyadenosine, and 2'-deoxycytidine. The presence of a 3'-phosphate group in the deoxyribose moiety was found to be compatible with this N-arylation reaction; further, oligonucleotides could serve as substrates. The facile nitroreduction of the coupling compounds (12) yielded 2'-deoxyguanosin-N2-ylarylamine adducts, which are known to be biologically important. Compound 12 was easily converted to phosphoramidite derivatives, allowing the preparation of site-specific modified oligonucleotides with arylamine after the nitroreduction. PMID:16839139

Takamura-Enya, Takeji; Enomoto, Shigeki; Wakabayashi, Keiji

2006-07-21

407

Discovery and SARs of trans-3-aryl acrylic acids and their analogs as novel anti-tobacco mosaic virus (TMV) agents.  

UK PubMed Central (United Kingdom)

A series of trans-3-aryl acrylic acids 1-27 and their derivatives 28-34 were prepared and evaluated for their antiviral activity against tobacco mosaic virus (TMV) for the first time. The bioassay results showed that most of these compounds exhibited good antiviral activity against TMV, of which compounds 1, 5, 6, 20, 27 and 34 exhibited significantly higher activity against TMV than commercial Ribavirin both in vitro and in vivo. Furthermore, these compounds have more simple structure than commercial Ribavirin, and can be synthesized more efficiently. These new findings demonstrate that trans-3-aryl acrylic acids and their derivatives represent a new template for antiviral studies and could be considered for novel therapy against plant virus infection.

Wu M; Wang Z; Meng C; Wang K; Hu Y; Wang L; Wang Q

2013-01-01

408

Synthesis and cytotoxicity of 3-aryl acrylic amide derivatives of the simplified saframycin-ecteinascidin skeleton prepared from l-dopa.  

UK PubMed Central (United Kingdom)

Twenty four compounds with diversified 3-aryl acrylic amide side chains of the simplified saframycin-ecteinascidin pentacyclic skeleton were synthesized via a 14-step stereospecific route starting from l-dopa. The cytotoxicities of these compounds were tested against eight human tumor cell lines including HCT-8, BEL-7402, BGC-803, A549, A2780, MCF-7, MX-1, and MDA-MB-231. Most of these compounds exhibited potent antitumor activity, and a preliminary structure-activity relationship (SAR) was discussed. Compound 28 with 3-thiophenyl acrylic amide side chain exhibited selective cytotoxicity against MDA-MB-231 cell line with the IC50 value of 50 nM.

Guo J; Dong W; Liu W; Yan Z; Wang N; Liu Z

2013-04-01

409

Synthesis of novel 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents.  

Science.gov (United States)

As a part of systematic investigation of synthesis and biological activities of indole analogues linked to various heterocyclic systems, we have synthesized new compounds viz., 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitriles (2a-i), 4,5-diamino-6-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-8-aryl-2-oxo-2,6-dihydrodipyrano [2,3-b:3,2-e]pyridine-3-carbonitriles (3a-i), 4-amino-5-(5'-substituted 2'-phenyl-1H-indol-3-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-ones (4a-i), 4-amino-5-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-thiones (5a-i), 4-(5'-subtituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-1,4-dihydropyrano[2,3-c]pyrazol-3-amines (6a-i) and 5-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-7-aryl-3H-pyrano[2,3-d]pyrimidin-4(5H)-ones (7a-i). Antibacterial activity results revealed that, compound 6a showed promising activity versus Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 6d exhibited good activity against S. aureus, K. pneumoniae and Pseudomonas aeruginosa. Antifungal activity results indicated that, compound 4d exhibited maximum zone of inhibition against Aspergillus oryzae and Aspergillus flavus. In case of antioxidant activity, compound 4a showed promising radical scavenging activity, ferric ions (Fe(3+)) reducing antioxidant power (FRAP) and metal chelating activity. PMID:23454016

Saundane, Anand R; Vijaykumar, Katkar; Vaijinath, A Verma

2013-02-16

410

Synthesis of novel 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents.  

UK PubMed Central (United Kingdom)

As a part of systematic investigation of synthesis and biological activities of indole analogues linked to various heterocyclic systems, we have synthesized new compounds viz., 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitriles (2a-i), 4,5-diamino-6-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-8-aryl-2-oxo-2,6-dihydrodipyrano [2,3-b:3,2-e]pyridine-3-carbonitriles (3a-i), 4-amino-5-(5'-substituted 2'-phenyl-1H-indol-3-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-ones (4a-i), 4-amino-5-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-7-aryl-1H-pyrano[2,3-d]pyrimidin-2(5H)-thiones (5a-i), 4-(5'-subtituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-1,4-dihydropyrano[2,3-c]pyrazol-3-amines (6a-i) and 5-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-7-aryl-3H-pyrano[2,3-d]pyrimidin-4(5H)-ones (7a-i). Antibacterial activity results revealed that, compound 6a showed promising activity versus Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 6d exhibited good activity against S. aureus, K. pneumoniae and Pseudomonas aeruginosa. Antifungal activity results indicated that, compound 4d exhibited maximum zone of inhibition against Aspergillus oryzae and Aspergillus flavus. In case of antioxidant activity, compound 4a showed promising radical scavenging activity, ferric ions (Fe(3+)) reducing antioxidant power (FRAP) and metal chelating activity.

Saundane AR; Vijaykumar K; Vaijinath AV

2013-04-01

411

Aryl hydrocarbon receptor and experimental autoimmune arthritis.  

Science.gov (United States)

Aryl hydrocarbon receptor (Ahr) is thought to be a crucial factor that regulates immune responses. Many Ahr-mediated immune regulatory mechanisms have been discovered, which will likely enhance our understanding of the molecular pathogenesis of autoimmune inflammation including rheumatoid arthritis (RA). RA is a systemic inflammatory disease that affects approximately 1 % of the population and is characterized by chronic inflammation of the synovium and subsequent joint destruction. Recent findings showed that Ahr plays critical roles in the development of Th17 cells, which are key effector T cells in a variety of human autoimmune diseases including RA. Consistent with these findings, our previous study demonstrated that Ahr in T cells is important for the development of collagen-induced arthritis, a widely used murine model of human RA, possibly via the induction of Th17 cells. In addition, Ahr is an attractive molecule because tobacco smoke is a well-known environmental risk factor for RA development and Ahr agonists, such as 2,3,7,8-tetrachlorodibenzo-p-dioxin, 3-methyl cholanthrene, and benzo[a]pyrene, are major toxic components in cigarettes. This review summarizes recent findings on Ahr functions in immune cells in the context of RA pathogenesis during stimulation with smoking-derived ligands. We also discuss the potential link between Ahr and novel factors, such as microRNAs, in the development of RA, thereby providing further mechanistic insight into this autoimmune disorder. PMID:23982178

Nguyen, Nam Trung; Nakahama, Taisuke; Kishimoto, Tadamitsu

2013-08-27

412

The ontogeny of nuclear aryl hydrocarbon hydroxylase.  

UK PubMed Central (United Kingdom)

The ontogeny of rat liver nuclear aryl hydrocarbon hydroxylase (AHH) ws studied. AHH which was barely detectable in 18--20 day fetal rat liver nuclei increased rapidly post-partum reaching a value which was over 200 times greater than the fetal liver specific activity. Nuclear AHH was induced upon administration of 3-methylcholanthrene (3-MC) to rats. The level of induction was dependent upon the age of the rat. Thus, the highest induced nuclear AHH specific activity was observed in the 3--4-week-old rat, i.e., 50--70 g in weight. The greatest fold increase in nuclear AHH after 3-MC administration was observed in the 6--8 g, or 1--2-day-old rat. Fetal rat liver nuclear AHH was also induced after 3-MC administration to the dam. The basal and induced levels of AHH were compared in nuclei and microsomes from 1--2 and 10--12-day-old rats. In the former, the ratio of the microsomal to nuclear AHH was 1.4 and 1.8 under basal and induced conditions, respectively.

Nunnink JC; Chuang AH; Bresnick E

1978-09-01

413

Metalorganic compounds  

UK PubMed Central (United Kingdom)

A transition metal organometallic compound contains a 2-indenyl ligand. An organometallic compound (I) of a transition metal and an optionally substituted 2-indenyl as a first ligand is of formula (I) excluding ethylene-bis(2-indenyl)-titanium dichloride, dimethylsilyl-(1-indenyl)(2-indenyl)-bis-dimethylamino-hafnium, dimethylsilyl-(1-indenyl)(2-indenyl)-bis-dimethylhafnium, dimethyl-bis(2-indenyl)silane-zirconium dichloride, 1-cyclopentadienyl-2-(2-indenyl)-ethane-zirconium chloride, bis-(2-indenyl)methane-zirconium dichloride, ethylene-1-(3-but-3-enyl)inden-1-yl)-2-((1-but-3-enyl)-inden-2-yl)zirc onium dichloride and ethylene-1,3-((3-allyldimethylsilyl)-indene-1-yl)-2-((1-allyldimethyls ilyl)-inden-2-yl)zirconium dichloride.; Independent claims are included for (i) a process for the production of (I) by mixing an optionally substituted 2-halo-indene of formula (II) with elementary Mg or Zn at (-) 20-120 degrees C in an amount of 1-100 g Mg or Zn per mole of indene and following separation of unreacted Mg or Zn, mixing with a dihalide of formula (III) in an amount of 1-20 moles per mole of indene (the addition of dihalide may occur simultaneously with that of Mg or Zn).; The resulting intermediate reaction product (II) of formula (IV) is mixed with a Z-derivative of formula (Va) or (Vb) (optionally after isolation of (II)) with formation of M<2>Hal<3> and/or R<9>Hal<3>, optionally in the presence of a base to form a 2-indenyl compound of formula (VI) with addition of a transition metal compound of formula (VII); (ii) tert-butylamido-2-indenyl-dimethylsilyl-titanium dichloride; (iii) the intermediate reaction product (II); and (iv) the preparation of (II).; Hal<2>-Y-Hal<3)<3) ZM<2>p (5a) ZR<9>p (5b) M<1>Xq (7) A = benzene or tetrahydrocyclohexyl; Q = 1-4C alkyl, 6-14C aryl, 7-10C aralkyl, 1-4C alkoxy, 1-4C alkylthio, phenoxy, phenylthio, di 1-4C alkylamino, 6-14C aryl-1-4C alkyl-amino, di-6-14C arylamino, dibenzylamino, tri-1-4C alkylsilyl, di-1-4C alkylboranyl, phenyl-1-4C alkyl-boranyl, diphenylboranyl di-1-4C alkyl-phosphoryl, diphenylphosphoryl or phenyl-1-4C-alkyl phosphoryl; m = 0-6; M<1> = a Group IV, V or VI transition metal; X = an anion; n = 0-4; Y = -C(R<1>R<2>)-, -Si(R<1>R<2>)-, -Ge(R<1>R<2>)-, -C(R<1>R<2>)-C(R<3>R<4>)-, -C(R<1>R<2>)-Si(R<3>R<4>)- or -Si(R<1>R<2>)-Si(R<3>R<4>); R<1>-R<4> = H, halogen, 1-10C alkyl, 5-8C cycloalkyl, 6-14C aryl or 7-10C aralkyl, ;; Z = a SIMILAR P system, optionally anionic, -N(R5)-, -P(R6)- or N(R5R7)-, P(R6R8)-, -O-, -S-, OR5- or SR5 having a free electron pair associated with N, P, O and/or S; R<5>-R<8> = R<1>-R<4>; R<5> and R<7> may also be -Si(R<1>R<2>R<3>) and R<6> and R<8> may also be -Si(R<1>R<2>R<3>), -OR<1>, -SR<1> or -N(R<1>R<2>); Hal<1>-Hal<3> = Cl, Br or I; Y = -Si(R<1>R<2>)-, -Ge(R<1>R<2>)- or -Si(R<1>R<2>)-Si(R<3>R<4>)-; M<2> = Li, Na or K or -MgHal<4>; Hal<4> = Hal<2>; p = 1 or 2; R<9> = H, -Si(R<1>R<2>R<3>) or S(R<1>R<2>R<3>); q = 2-6.

LANG HEINRICH PROF. DR; WEISS THOMAS; BECKE SIGURD DR

414

Tuning Aryl?CH···O Intermolecular Interactions on Pt(111)  

DEFF Research Database (Denmark)

Scanning tunneling microscopy (STM) data are reported for the room-temperature adsorption of 2,2,2-trifluoroacetophenone (TFAP), 2,2,2-trifluorovinylbenzene (TFVB), octafluoroacetophenone (OFAP), and methyl benzoate (MB) on Pt(111). The objective of the study is to establish the role of aryl?CH···O bonding in forming self-assembled low-nuclearity structures at room temperature and to compare aryl?CH···O bonding by ester and ketone carbonyl functions. The STM images clearly evidence the formation of homochiral dimers and trimers of TFAP, and density functional theory (DFT) calculations reveal aryl?CH···O bonding as the driving force for dimer formation. In contrast to TFAP, chemisorbed TFVB and OFAP do not form such self-assembled structures as they lack carbonyl and aryl?CH groups, respectively. The self-assembly of MB on Pt(111) differs from that of TFAP, in that it can form structures stabilized by one, as distinct from two, aryl?CH···O bonds. The results are discussed with respect to the enantioselective hydrogenation of ?-ketoesters on cinchona modified Pt catalysts.

Demers-Carpentier, Vincent; Laliberte, Marc-Andre?

2011-01-01

415

Synthesis and in-vitro antibacterial activity of some alkoxy based N-substituted-5-(furan-2-yl)-phenyl-bis-pyrazolines  

Directory of Open Access Journals (Sweden)

Full Text Available Bis-pyrazoline darivatives (2a-e) built around the alkyl chains of varying length were synthesized in good yield by refluxing bis-chalcones (1a-e) with phenyl hydrazine in CH3COOH and ethanol. The structures of these compounds were elucidated by IR, 1H NMR, 13C NMR, Mass (ESI) spectrometries and their purities were confirmed by elemental analyses. The antibacterial activity of these compounds were evaluated by the disc diffusion assay against two Gram-positive and two Gram-negative bacteria and then the minimum inhibitory concentration of compounds were determined. The compounds 1,4-bis[1-(2-oxyphenyl)-5-(furan-2-yl)-4,5-dihydro-1H-pyrazole] butane (2a) and 1,10-bis[1-(2-oxyphenyl)-5-(furan-2-yl)-4,5-dihydro-1H-pyrazole]decane (2e) are better antibacterial agent as compared to Tetracycline and Gentamicin.

Mamta Rani; Mohamad Yusuf

2012-01-01

416

Some higher N-substituted 1,3-thiazolidine-2,4-diones and 5,5-diphenylhydantoins, their synthesis and corrosion preventive properties in mineral oil medium  

Science.gov (United States)

Some five membered heterocyclic compounds were synthesized by the reaction of 2,4-thiazolidinedione or 5,5-diphenylhydantoin potassium salts with 2-chloro-N-alkylacetamides and alkyl-2-chloroacetates. The structure confirmations of the synthesized compounds were performed by FT-IR, 1H NMR, 13C NMR spectra. The inhibitory effectiveness of the compounds were evaluated against the corrosion of steel strip immersed in water containing paraffin based mineral oil medium in accordance to standard test method. Surface characterization studies of the metal coupons used were performed by SEM analysis and also by the contact angle measurements using the Sessile-Drop method. In addition the 3D image of the metal surface was obtained using optical profilometer. The test results and surface characterization studies showed that all synthesized compounds are excellent corrosion inhibitors in such a water in oil emulsion system.

Öztürk, Serkan; Yildirim, Ayhan; Çetin, Mehmet

2013-01-01

417

The acid-mediated ring opening reactions of ?-aryl-lactams.  

UK PubMed Central (United Kingdom)

4-Aryl-azetidin-2-ones (?-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl exchange. Lactams of ring size 7 and higher also ring open, but only 7- and 8-membered rings give pure diphenylalkylamides. AlCl(3) only ring opens the 4-aryl-azetidinones.

King FD; Caddick S

2012-04-01

418

The acid-mediated ring opening reactions of ?-aryl-lactams.  

Science.gov (United States)

4-Aryl-azetidin-2-ones (?-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl exchange. Lactams of ring size 7 and higher also ring open, but only 7- and 8-membered rings give pure diphenylalkylamides. AlCl(3) only ring opens the 4-aryl-azetidinones. PMID:22406974

King, Frank D; Caddick, Stephen

2012-03-12

419

Carbon-Hydrogen Bond Functionalization Approach for the Synthesis of Fluorenones and ortho-Arylated Benzonitriles  

Science.gov (United States)

A palladium-catalyzed benzamide ortho-arylation/reaction with (CF3CO)2O sequence was developed allowing a convenient one-pot synthesis of ortho-arylated benzonitriles and fluorenone derivatives. The outcome of this transformation is dependent on the amide N-alkyl substituent. Dehydration of ortho-arylated N-cyclohexyl-benzamides by (CF3CO)2O results in efficient production of benzonitriles. In contrast, o-arylated N-propylbenzamides are converted to fluorenone derivatives.

Shabashov, Dmitry; Molina Maldonado, Jesus R.; Daugulis, Olafs

2009-01-01

420

The acid-mediated ring opening reactions of ?-aryl-lactams.  

Digital Repository Infrastructure Vision for European Research (DRIVER)

4-Aryl-azetidin-2-ones (?-lactams) undergo ring opening with triflic acid to give cinnamamides which, in benzene, react further to give 3-aryl-3-phenyl-propionamides. Prolonged reaction times in benzene give 3,3-diphenyl-propionamide via an aryl/phenyl exchange. Lactams of ring size 7 and higher als...

King, FD; Caddick, S

 
 
 
 
421

Manganese-catalyzed cross-coupling of thiols with aryl iodides.  

UK PubMed Central (United Kingdom)

A manganese-catalyzed cross-coupling reaction of thiols with aryl iodides, furnishing aryl thioethers in good to excellent yields has been reported; the system shows good functional group tolerance and enables the sterically demanding aryl iodides to couple with thiols.

Liu TJ; Yi CL; Chan CC; Lee CF

2013-05-01

422

Nickel-catalyzed reductive allylation of aryl bromides with allylic acetates.  

Science.gov (United States)

This paper highlights Ni-catalyzed allylation of electron-rich aryl bromides with a variety of substituted allylic carbonates using zinc as the terminal reductant, affording E-alkenes regioselectively in good to excellent yields by the addition of aryl to the less hindered allylic carbon. The electron-deficient aryl bromides and chlorides are also highly efficient coupling partners. PMID:23576012

Cui, Xiaozhan; Wang, Shulin; Zhang, Yuwei; Deng, Wei; Qian, Qun; Gong, Hegui

2013-04-10

423

Nickel-catalyzed reductive allylation of aryl bromides with allylic acetates.  

UK PubMed Central (United Kingdom)

This paper highlights Ni-catalyzed allylation of electron-rich aryl bromides with a variety of substituted allylic carbonates using zinc as the terminal reductant, affording E-alkenes regioselectively in good to excellent yields by the addition of aryl to the less hindered allylic carbon. The electron-deficient aryl bromides and chlorides are also highly efficient coupling partners.

Cui X; Wang S; Zhang Y; Deng W; Qian Q; Gong H

2013-05-01

424

Effects of Lewis acid catalysts on the cleavage of aliphatic and aryl-aryl linkages in coal-related structures  

Energy Technology Data Exchange (ETDEWEB)

ZnClat2 and AlClat3 catalyse the cleavage of aliphatic linkages between aromatic nuclei but not the cleavage of direct aryl-aryl bonds between such nuclei. The rate of alkyl-aryl bond breakage depends on the Broensted acidity of the active catalyst (e.g. Hat+(ZnClat2X)at- or Hat+(AlClat3X)at-) and the Broensted basicity of the aromatic portions of the reactant. AlClat3 is significantly more active than ZnClat2, and reactants containing hydroxyphenyl or napthyl groups are more reactive than those containing phenyl groups. The distribution of final products is strongly affected by the reactions of the aryl-alkyl carbonium ion formed upon cleavage of an alkyl-aryl bond. If the alkyl portion of the carbonium ion contains three or more carbon atoms, the ion preferentially undergoes an intramolecular reaction to form a hydroaromatic product. With only one or two carbon atoms the carbonium ion reacts via either hydride abstraction or electrophilic substitution, the hydride abstraction producing an alkyl-aromatic product, which may in turn undergo dealkylation. Reactant and products produced by a Scholl condensation act as the principle sources of hydride ions. Molecular Hat2 also contributes some hydride ions. The reaction of carbonium ions by electrophilic substitution leads either to the regeneration of the initial reactant or to the formation of high-molecular-weight tars. (24 refs.)

Taylor, N.D.; Bell, A.T.

1980-07-01

425

Photoreactive molecular layers containing aryl ester units: Preparation, UV patterning and post-exposure modification  

International Nuclear Information System (INIS)

The photolithographic modification of thin functional silane layers provides a versatile and powerful means of fabricating functionalized patterned surfaces which can be applied for tuning inorganic surface properties and for modern immobilisation techniques. In this contribution we present the synthesis of a new functional trichloro organosilane bearing photoreactive aryl ester groups and its application in thin silane layers on silicon oxide surfaces. Whereas the trichlorosilyl group acts as anchoring unit to the inorganic surface, the aryl ester group undergoes the photo-Fries rearrangement to yield hydroxyketones upon irradiation with UV-light of 254 nm which leads to a change in chemical reactivity of the surface. By a subsequent reaction with perfluorobutyryl chloride, the photogenerated hydroxy groups yield the corresponding perfluorinated ester compound, which allows further tuning of surface properties. The layer formation as well as the photoreaction and post-modification reaction was monitored by FTIR spectroscopy and X-ray photoelectron spectroscopy (XPS). The thickness of the obtained thin layers was determined by X-ray reflectivity (XRR). Photopatterned surfaces were produced using a contact mask during illumination followed by the post-modification reaction. Friction force microscopy (FFM) revealed the contrast between modified and unmodified regions of the patterned samples.

2010-01-15

426

METHOD FOR SYNTHESIS OF N,N-DIALKYLAMIDOFLUOROANHYDRIDES OF ALKYL(ARYL)PHOSPHONOUS ACIDS  

UK PubMed Central (United Kingdom)

FIELD: chemistry. ^ SUBSTANCE: invention relates to a method for synthesis of N,N-dialkylamidofluoroanhydrides of alkyl(aryl)phosphonous acids of general formula: RP(NR2')F, where R=CH3, C2H5, i-C3H7, C6H5 NR2'=(CH3)2N, (C2H5)2N, (i-C4H9)2N, (C4H9)2N, ^ ^ and can be used in organic synthesis. Method involves treatment of alkyl(aryl)difluorophosphines of formula RPF2 with trimethylsilyl amines of general formula (CH3)3Si(NR'2), where NR2'= (CH3)2N, (C2H5)2N, (i-C4H9)2N, (C4H9)2N, ^ ^ at -30-20C for 30-60 minutes. ^ EFFECT: design of a novel method for synthesis of compounds needed in organic synthesis. ^ 1 cl, 2 ex, 2 tbl

KROLEVETS ALEKSANDR ALEKSANDROVICH

427

4?-[4'-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and II? inhibitors and apoptosis inducing agents.  

Science.gov (United States)

A series of 4?-[4'-(1-(aryl)ureido)benzamide]podophyllotoxin congeners (11a-l) were synthesized and evaluated for their cytotoxic activity against six human cancer cell lines. Some of the compounds like 11a, 11h, 11k and 11l showed significant anti-proliferative activity in Colo-205 cells and were superior to etoposide. The flow-cytometric analysis studies indicated that these compounds show strong G1 cell cycle arrest, as well exhibited improved inhibitory activities on DNA topoisomerase I and II? enzymes. These compounds induce apoptosis by up regulating caspase-3 protein as observed by ELISA and Western blotting analysis. In addition, a brief structure-activity relationship studies within the series along with docking results of representative compounds 11a, 11h, 11k, 11l were presented. PMID:23849207

Kamal, Ahmed; Suresh, Paidakula; Ramaiah, M Janaki; Srinivasa Reddy, T; Kapavarapu, Ravi Kumar; Rao, Bolla Narasimha; Imthiajali, Syed; Lakshminarayan Reddy, T; Pushpavalli, S N C V L; Shankaraiah, Nagula; Pal-Bhadra, Manika

2013-06-21

428

4?-[4'-(1-(Aryl)ureido)benzamide]podophyllotoxins as DNA topoisomerase I and II? inhibitors and apoptosis inducing agents.  

UK PubMed Central (United Kingdom)

A series of 4?-[4'-(1-(aryl)ureido)benzamide]podophyllotoxin congeners (11a-l) were synthesized and evaluated for their cytotoxic activity against six human cancer cell lines. Some of the compounds like 11a, 11h, 11k and 11l showed significant anti-proliferative activity in Colo-205 cells and were superior to etoposide. The flow-cytometric analysis studies indicated that these compounds show strong G1 cell cycle arrest, as well exhibited improved inhibitory activities on DNA topoisomerase I and II? enzymes. These compounds induce apoptosis by up regulating caspase-3 protein as observed by ELISA and Western blotting analysis. In addition, a brief structure-activity relationship studies within the series along with docking results of representative compounds 11a, 11h, 11k, 11l were presented.

Kamal A; Suresh P; Ramaiah MJ; Srinivasa Reddy T; Kapavarapu RK; Rao BN; Imthiajali S; Lakshminarayan Reddy T; Pushpavalli SN; Shankaraiah N; Pal-Bhadra M

2013-09-01

429

Synthesis and biological evaluation of a novel series of aryl S,N-ketene acetals as antileishmanial agents.  

Science.gov (United States)

A series of aryl S,N-ketene acetals 7(a-f) was synthesized and evaluated for their in vitro and in vivo antileishmanial activity against Leishmania donovani. All the 6 compounds exhibited significant in vitro activity against intracellular amastigotes of L. donovani with IC50 values ranging from 1.2 to 3.5 ?M and were found promising as compared with reference drugs, sodium stibogluconate (SSG) and paromomycin. On the basis of good selectivity indices (SI), they were further tested for their in vivo potential against L. donovani/hamster model. Two compounds 7a and 7b showed significant inhibition of parasite multiplication, 72% and 83%, respectively. These compounds were comparable with SSG and superior to paromomycin. Preliminary in vitro metabolic investigations were also performed to assess the metabolic stability and in vitro hepatic intrinsic clearance (Clint) of compound 7b in hamster liver microsomes. PMID:23673014

Suryawanshi, S N; Kumar, Santosh; Tiwari, Avinash; Shivahare, Rahul; Chhonker, Yashpal Singh; Pandey, Susmita; Shakya, Nishi; Bhatta, Rabi Sankar; Gupta, Suman

2013-04-26

430

Synthesis and biological evaluation of a novel series of aryl S,N-ketene acetals as antileishmanial agents.  

UK PubMed Central (United Kingdom)

A series of aryl S,N-ketene acetals 7(a-f) was synthesized and evaluated for their in vitro and in vivo antileishmanial activity against Leishmania donovani. All the 6 compounds exhibited significant in vitro activity against intracellular amastigotes of L. donovani with IC50 values ranging from 1.2 to 3.5 ?M and were found promising as compared with reference drugs, sodium stibogluconate (SSG) and paromomycin. On the basis of good selectivity indices (SI), they were further tested for their in vivo potential against L. donovani/hamster model. Two compounds 7a and 7b showed significant inhibition of parasite multiplication, 72% and 83%, respectively. These compounds were comparable with SSG and superior to paromomycin. Preliminary in vitro metabolic investigations were also performed to assess the metabolic stability and in vitro hepatic intrinsic clearance (Clint) of compound 7b in hamster liver microsomes.

Suryawanshi SN; Kumar S; Tiwari A; Shivahare R; Chhonker YS; Pandey S; Shakya N; Bhatta RS; Gupta S

2013-07-01

431

A New Route to Azafluoranthene Natural Products via Direct Arylation.  

UK PubMed Central (United Kingdom)

Microwave-assisted direct arylation was successfully employed in the synthesis of azafluoranthene alkaloids for the first time. Direct arylation reactions on a diverse set of phenyltetrahydroisoquinolines produces the indeno[1,2,3-ij]isoquinoline nucleus en route to a high yielding azafluoranthene synthesis. The method was used as a key step in the efficient preparation of the natural products rufescine and triclisine. As demonstrated herein, this synthetic approach should be generally applicable to the preparation of natural and un-natural azafluoranthene alkaloids as well as "azafluoranthene-like" isoquinoline alkaloids.

Ponnala S; Harding WW

2013-02-01

432

Discovery of Novel Lead in the Group of N-substituted Piperazine Ether Derivatives with Potential Histamine H3 Receptor Activity.  

UK PubMed Central (United Kingdom)

The search for novel lead from the group of various substituted N-piperazine ether derivatives was performed. Acyl- and pyridylpiperazine ethyl/propyl ethers were obtained via three different synthetic pathways. Affinity to histamine H3 receptor was established, as well as, for selected compounds, selectivity towards histamine H4R. Docking studies to the histamine H3R homology model strengthened the position of (4-(3-(4-(3-chlorobenzoyl)piperazin-1-yl)propoxy)phenyl)(cyclopropyl)methanone (compound 26) as a novel lead for further studies on histamine H3 receptor antagonist/inverse agonist.

K J Kuder; Stachnik M; Schunack W; Szyma?ska E; Kie?-Kononowicz K

2013-09-01

433

An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with ?-iminoesters.  

Science.gov (United States)

The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-?-iminoesters affords aryl carboxylic esters via carbonyl-imino ? bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation. PMID:23939012

Qian, Cheng; Chen, Jiayan; Fu, Meiqin; Zhu, Shiya; Chen, Wen-Hua; Jiang, Huanfeng; Zeng, Wei

2013-09-28

434

Access to ?-Keto Esters by Palladium-Catalyzed Carbonylative Coupling of Aryl Halides with Monoester Potassium Malonates.  

Science.gov (United States)

New tricks for an old dog: The Pd-catalyzed carbonylative ?-arylation of monoethyl potassium malonates with aryl bromides and reactive aryl chlorides provides a simple and direct route to aryl ?-ketoesters. Because only stoichiometric amounts of carbon monoxide are employed, the method is ideal for the introduction of carbon isotopes into more complex structures. PMID:23881598

Korsager, Signe; Nielsen, Dennis U; Taaning, Rolf H; Skrydstrup, Troels

2013-07-23

435

Synthesis and pharmacological profile of novel N-substituted N-[5H-[1]benzopyrano[4,3-d]pyrimidin-2-YL]-N-methylglycinamides.  

Science.gov (United States)

The title compounds were synthesized by cyclizing 3-dimethylaminomethylene-4-chromanone with creatine to give the acid 2 that was successively converted into the corresponding amides 3a-f via diphenylphosphorylazide and the relevant amines. The free acid 2 and some of 3a-f showed antiinflammatory, hypotensive and antiarrhythmic properties. PMID:8857210

Bruno, O; Schenone, S; Ranise, A; Bondavalli, F; D'Amico, M; Filippelli, W; Berrino, L; Rossi, F

1996-02-01

436

Synthesis and pharmacological profile of novel N-substituted N-[5H-[1]benzopyrano[4,3-d]pyrimidin-2-YL]-N-methylglycinamides.  

UK PubMed Central (United Kingdom)

The title compounds were synthesized by cyclizing 3-dimethylaminomethylene-4-chromanone with creatine to give the acid 2 that was successively converted into the corresponding amides 3a-f via diphenylphosphorylazide and the relevant amines. The free acid 2 and some of 3a-f showed antiinflammatory, hypotensive and antiarrhythmic properties.

Bruno O; Schenone S; Ranise A; Bondavalli F; D'Amico M; Filippelli W; Berrino L; Rossi F

1996-02-01

437

Palladium-catalyzed cross-coupling of pyrrole anions with aryl chlorides, bromides, and iodides.  

Science.gov (United States)

[reaction: see text] A general method for the conversion of pyrrole anions to 2-arylpyrroles has been developed. Using a palladium precatalyst and sterically demanding 2-(dialkylphosphino)biphenyl ligands, (pyrrolyl)zinc chloride may be cross-coupled with a wide range of aryl halides, including aryl chlorides and aryl bromides, at low catalyst loadings and under mild conditions. A high degree of steric hindrance is tolerated. Certain ring-substituted pyrrole anions have also been arylated with aryl bromide substrates. PMID:15496079

Rieth, Ryan D; Mankad, Neal P; Calimano, Elisa; Sadighi, Joseph P

2004-10-28

438

Synthesis and antiviral bioactivity of novel (1E, 4E)-1-aryl-5-(2-(quinazolin-4-yloxy)phenyl)-1,4-pentadien-3-one derivatives.  

UK PubMed Central (United Kingdom)

A series of novel (1E, 4E)-1-aryl-5-[2-(quinazolin-4-yloxy)phenyl]-1,4-pentadien-3-one derivatives were designed and synthesized by reacting substituent aldehyde with intermediates 4a-f. Antiviral bioassays indicated that most of the compounds exhibited promising ex vivo antiviral bioactivities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) at 500 ?g/mL. The relationship between structure and antiviral activity was also discussed. Compounds 5a, 6e, and 6g could possess appreciable protective bioactivities on TMV ex vivo by approximately 50% (EC50) at 257.7, 320.7 and 243.3 ?g/mL. This study is the first to demonstrate that (1E, 4E)-1-aryl-5-(2-(quinazolin-4-yloxy)phenyl)-1,4-pentadien-3-one can be used to develop potential virucides for plants.

Luo H; Liu J; Jin L; Hu D; Chen Z; Yang S; Wu J; Song B

2013-05-01

439

Direct Arylation of Oligonaphthalenes Using PIFA/BF3·Et2O: From Double Arylation to Larger Oligoarene Products.  

Science.gov (United States)

Direct dehydrogenative coupling between the linear ter- and quaternaphthalenes and substituted benzenes was achieved under the Kita conditions using the hypervalent PIFA/BF3 reagent. Products resulting from either the double arylation of the naphthalenic substrate or the formal dimerizative arylation have been prepared. For example, in the latter mode, ternaphthalene was converted into a series of linear octiarenes (counting the capping Ar). The process represents an alternative to the cross-coupling methodologies employed in related syntheses and proceeds via a selective functionalization of six relatively inert aromatic CH bonds. PMID:23859634

Guo, Wusheng; Faggi, Enrico; Sebastián, Rosa M; Vallribera, Adelina; Pleixats, Roser; Shafir, Alexandr

2013-08-02

440

UV-vis spectroscopy of the coupling products of the palladium-catalyzed C-H arylation of the BODIPY core.  

UK PubMed Central (United Kingdom)

The steady-state, UV-vis electronic absorption and fluorescence emission properties of a large set of 3-aryl and 3,5-diaryl substituted difluoroboron dipyrromethene dyes obtained via direct, palladium-catalyzed C-H (het)arylation of the BODIPY core are reported. The spectra display the narrow absorption and fluorescence emission bands and the generally quite small Stokes shifts characteristic of classic difluoroboron dipyrrins. As a function of the solvent, the spectral maxima are located within a very narrow wavelength range and are slightly red-shifted with increasing solvent polarizability, which is shown to be the crucial parameter influencing the wavelength position of the maxima. The extended ?-conjugation in the 3,5-diaryl products always leads to bathochromically shifted absorption and emission spectra compared to those of the 3-aryl analogues. The derivative with a 3-mesityl substituent has blue-shifted spectra in comparison to its 3-phenyl substituted analogue, reflecting the diminished ?-conjugation in the former due to steric strain. The nature of the meso-aryl has only a small effect on the spectral positions but affects the fluorescence quantum yield ?. The majority of the dyes have high ? (>0.85), except the compounds with meso-phenyl and meso-(p-nitrophenyl) substituents. Quantum-chemical calculations were performed to evaluate the differences in spectroscopic properties upon substitution of the BODIPY core and to compare them with the corresponding experimental results.

Wang L; Verbelen B; Tonnelé C; Beljonne D; Lazzaroni R; Leen V; Dehaen W; Boens N

2013-05-01

 
 
 
 
441

Asymmetrical Aryl Amine Derivative for Organic Electroluminescence Devices, Method for Preparing Same, Organic Thin Film for Organic Electroluminescence Devices and Organic Electroluminescence Device Using Same  

UK PubMed Central (United Kingdom)

Provided are asymmetric arylamine derivatives for an organic electroluminescent element, represented by the formula (1), which is prepared by sequentially inducing a secondary amine and a tertiary amine to an aryl compound Ar core so that they do not include a symmetrical axis and a symmetrical surface in a molecule, a manufacturing method of the same, an organic thin layer material including the asymmetric arylamine derivatives, and an organic electroluminescent element employing the same: wherein Ar represents a C10-C20 divalent aryl group, Ar1 is a divalent C6-C30 aryl group, and Ar2 to Ar5 each independently represents a divalent C6-C30 aryl group, at least one of Ar2 to Ar5 having a different structure when the secondary amine and the tertiary amine in Ar are substituted at symmetrical positions, and Ar2 to Ar5 having the same structure or different structures when the secondary amine and the tertiary amine in Ar are substituted at asymmetrical positions. The asymmetric arylamine derivative can be used in forming an organic thin layer for an organic electroluminescent element. When the organic electroluminescent element is formed using a dopant as an emitting material, the asymmetric arylamine derivative exhibits superb emission efficiency and an excellent lifetime characteristic in a blue wavelength region.

KIM SANG DONG; KIM SE HUN; LEE JI HYE; OH YONG HO