Sample records for aminotoluenes

  1. Use of genetically manipulated Salmonella typhimurium strains to evaluate the role of human sulfotransferases in the bioactivation of nitro- and aminotoluenes. (United States)

    Glatt, Hansruedi; Sabbioni, Gabriele; Monien, Bernhard H; Meinl, Walter


    Various nitro- and aminotoluenes demonstrated carcinogenic activity in rodent studies, but were inactive or weakly active in conventional in vitro mutagenicity assays. Standard in vitro tests do not take into account activation by certain classes of enzymes. This is true in particular for sulfotransferases (SULTs). These enzymes may convert aromatic hydroxylamines and benzylic alcohols, two major classes of phase-I metabolites of nitro- and aminotoluenes, to reactive esters. Here it is shown that expression of certain human SULTs in Salmonella typhimurium TA1538 or TA100 strongly enhanced the mutagenicity of various nitrotoluenes and nitro- and amino-substituted benzyl alcohols. Human SULT1A1, SULT1A2, and SULT1C2 showed the strongest activation. The observation that some nitrotoluenes as well as some aminobenzyl alcohols were activated by SULTs in the absence of cytochromes P450 implies that mutagenic sulfuric esters were formed at both the exocyclic nitrogen and the benzylic carbon, respectively. Nitroreductase deficiency (using strain YG7131 instead of TA1538 for SULT1A1 expression) did not affect the SULT-dependent mutagenicity of 1-hydroxymethylpyrene (containing no nitro group), moderately enhanced that of 2-amino-4-nitrobenzyl alcohol, and drastically attenuated the effects of nitrobenzyl alcohols without other substituents. The last finding suggests that either activation occurred at the hydroxylamino group formed by nitroreductase or the nitro group (having a strong -M effect) had to be reduced to an electron-donating substituent to enhance the reactivity of the benzylic sulfuric esters. The results pointed to an important role of SULTs in the genotoxicity of nitrotoluenes and alkylated anilines. Activation occurs at nitrogen functions as well as benzylic positions. Environ. Mol. Mutagen. 57:299-311, 2016. © 2016 Wiley Periodicals, Inc. PMID:26924705

  2. Synthesis and characterization of binary and ternary complexes of Co(II), Ni(II), Cu(II) and Zn(II) ions based on 4-aminotoluene-3-sulfonic acid (United States)

    Faheim, Abeer A.; Abdou, Safaa N.; Abd El-Wahab, Zeinab H.


    Salicylidene (4-aminotoluene-3-sulfonic acid) Schiff base ligand H2L, and its binary and ternary Co(II), Ni(II), Cu(II) and Zn(II) complexes using 8-hydroxyquinoline (8-HOqu) and 2-aminopyridine (2-Ampy) as secondary ligands have been synthesised and characterized via elemental analysis, spectral data (IR, 1H NMR, mass and solid reflectance), molar conductance, magnetic moment, TG-DSC measurements and XRPD analysis. Correlation of all spectroscopic data suggest that H2L ligand acts as monoanionic terdentate ligand with ONO sites coordinating to the metal ions via deprotonated phenolic-O, azomethine-N and sulfonate-O while 2-Ampy behaves as a neutral monodentate ligand via amino group-N and 8-HOqu behaves as a monoanionic bidentate ligand through the ring-N and deprotonated phenolic-O. The thermal behavior of these complexes shows that the coordinated water molecules were eliminated from the complexes at relatively higher temperatures than the hydrated water and there are two routes in removal of coordinated water molecules. All complexes have mononuclear structure and the tetrahedral, square planar or an octahedral geometry have been proposed. The ligand and its complexes have been screened for their antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Salmonella typhimurium, Candida albicans and Aspergillus fumigatus. Among the synthesised compounds, the binary and ternary Ni(II) complexes, (2, 8 and 10) and ternary Zn(II) complex, (12) were found to be very effective against Candida albicans and Bacillus subtilis than all other complexes with MICs of 2 and 8 μg/mL, respectively.

  3. (6E-N-[(4Z-2,5-Dimethyl-4-(p-tolyliminocyclohexa-2,5-dienylidene]-4-methylaniline

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    Fang-Fang Jian


    Full Text Available The title compound, C22H22N2, was prepared by the reaction of 4-aminotoluene with sodium carbonate, sodium hydroxide and potassium permanganate. The molecule is disposed about a crystallographic inversion centre with one half-molecule comprising the asymmetric unit. The dihedral angle between the terminal and central benzene rings is 88.05 (1°. The crystal packing is stabilized by van der Waals forces.

  4. Interaction Studies between Newly Synthesized Photosensitive Polymer and Ionic Liquids

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    In Tae Kim


    Full Text Available In this information age, different kinds of photosensitive materials have been used in the manufacture of information storage devices. But these photosensitive materials have the bane of low diffraction efficiency. In order to solve this problem, we have synthesized a novel photosensitive polymer from epoxy-based azopolymers (with three types of azochromophores. Furthermore, we have studied the interaction between this newly synthesized azopolymer and ionic liquids (ILs. For this purpose, we have used the ammonium and imidazolium families of ILs, such as diethylammonium dihydrogen phosphate (DEAP, tributylammonium methyl sulfate (TBMS, triethylammonium 4-aminotoluene-3-sulfonic acid (TASA, and 1-methylimidazolium chloride ([Mim]Cl. To investigate the molecular interaction between azopolymer and ILs, we have used the following spectroscopic methods of analysis: UV-visible spectroscopy, photoluminescence (PL spectroscopy, Fourier transformed infrared spectroscopy (FT-IR, and confocal Raman spectroscopy. In this study, we have developed new photosensitive materials by combining polymer with ILs.

  5. Catalytic oxidation of 2-aminophenols and ortho hydroxylation of aromatic amines by tyrosinase

    International Nuclear Information System (INIS)

    The usual substrates of tyrosinase, a copper-containing monooxygenase (EC, are monophenols and o-diphenols which are both converted to o-quinones. In this paper, the authors studied the reaction of this enzyme with two new classes of substrates: aromatic amines and o-aminophenols, structural analogues of monophenols and o-diphenols, respectively. They undergo the same catalytic reactions (ortho hydroxylation and oxidation), as documented by product analysis and kinetic studies. In the presence of tyrosinase, arylamines and o-aminophenols are converted to o-quinone imines, which are isolated as quinone anils or phenoxazones. As an example, in the presence of tyrosinase, 2-amino-3-hydroxybenzoic acid (an o-aminophenol) is converted to cinnabarinic acid, a well-known phenoxazone, while p-aminotoluene (an aromatic amine) gives rise to the formation of 5-amino-2-methyl-1,4-benzoquinone 1-(4-methylanil). Kinetic studies using an oxygen electrode show that arylamines and the corresponding monophenols exhibit similar Michaelis constants. In contrast, the reaction rates observed for aromatic amines are relatively slow as compared to monophenols. The enzymatic conversion of arylamines by tryosinase is different from the typical ones: N-oxidation and ring hydroxylation without further oxidation. This difference originates from the regiospecific hydroxylation (ortho position) and subsequent oxidation of the intermediate o-aminophenol to the corresponding o-quinone imine. Finally, the well-know monooxygenase activity of tyrosinase was also confirmed for the aromatic amine p-aminotoluene, with 18O2

  6. Development of electrochemical sensors for trace detection of explosives and for the detection of chemical warfare agents (United States)

    Berger, T.; Ziegler, H.; Krausa, Michael


    A huge number of chemical sensors are based on electrochemical measurement methods. Particularly amperometric sensorsystems are employed for the fast detection of pollutants in industry and environment as well as for analytic systems in the medical diagnosis. The large number of different applications of electrochemical sensors is based on the high sensitivity of electrochemical methods and on the wide of possibilities to enhance the selectivity by variation of electrochemical and chemical parameters. Besides this, electrochemical sensorsystems are frequently simple to operate, transportable and cheap. Up to now the electrochemical method of cyclic voltammetry is used only seldom for sensors. Clearly the efficiency of cyclic voltammetry can be seen at the sensorsystem for the detection of nitro- and aminotoluenes in solids and waters as presented here. The potentiodynamic sensors system can be employed for the fast and easy risk estimation of contaminated areas. Because of the high sensitivity of electrochemical methods the detection of chemical substances with a low vapor pressure is possible also. The vapor pressure of TNT at room temperature is 7 ppb for instances. With a special electrochemical set-up we were able to measure TNT approximately 10 cm above a TNT-sample. In addition we were able to estimate TNT in the gaseous phase approximately 10 cm above a real plastic mine. Therefore it seems to be possible to develop an electrochemical mien detection. Moreover, we present that the electrochemical detection of RDX, HMX and chemical warfare agents is also possible.

  7. Fine CuO anisotropic nanoparticles supported on mesoporous SBA-15 for selective hydrogenation of nitroaromatics. (United States)

    Sareen, Shweta; Mutreja, Vishal; Singh, Satnam; Pal, Bonamali


    SBA-15 modified with APTMS (3-aminopropyl trimethoxysilane) having pore diameter (∼8 nm) has been synthesized and impregnated with 1-10 wt.% Cu using Cu(NO3)2 as a metal source followed by calcination at 350 °C. As-prepared CuO/ap-SBA-15 powder showed changes in the color from white for bare SBA-15 to light green due to formation of anisotropic CuO nanoparticles that exhibited a characteristic plasmon absorption band at 359 and 747 nm. TEM studies showed a change in the morphology of CuO NPs as a function of increased Cu loading. Moreover, well dispersed CuO nanospheres (∼5-6 nm) and nanorods (aspect ratio ∼11-20 nm) having monoclinic crystal phase were observed within the mesoporous channels of SBA-15. Elemental mapping studies confirmed uniform distribution of CuO nanoparticles on the surface of SBA-15. An increase in surface area was also observed from 694 m(2) g(-1) for SBA-15 to 762 m(2) g(-1) for 10 wt.% Cu loading probably due to the deposition of excess of CuO nanoparticles on the outer siliceous surface. The catalytic activity also increased with Cu loading and 10 wt.% CuO/ap-SBA-15 catalyst displayed the highest catalytic activity for the reduction of m-chloronitrobenzene and m-nitrotoluene with 83% and 100% selectivity for m-chloroaniline and m-aminotoluene respectively. PMID:26397928


    Institute of Scientific and Technical Information of China (English)

    王建华; 郭晓宇; 任畅; 渠弼


    Objective:To search for compounds of Schiff base which have both vanillin's bioactivity and Schiff bases. They could be used as sedative,antiepileptic and anticancer drugs. Methods:Tetra-o-acetyl-α-D-vanillin-glucoside was synthesized by acetylation and bromination and other steps with glucose and vanillin. It was reacted with p-aminotoluene. Result: Compound V was obtained and the structure of it was identified by PE 2400、IR、1 HNMR. Conclusion:Schiff base can be synthesized by structure reformation and modification on vanillin based on Combination Principle of Medicine[1] .%目的:香草醛( vanillin)是一种重要的天然产物,具有镇静、催眠、止痛、抗癫痫等生物活性,希夫碱是具有抗炎、杀菌作用的亚胺类化合物。此项研究的目的就是要找到兼有香草醛的活性和希夫碱功效的化合物,筛选具有镇静、抗癫痫、抗癌的药物。方法:以葡萄糖、香草醛为原料经过乙酰化,溴代等步骤合成了中间体四乙酰葡萄糖香草醛苷,然后与对甲苯胺反应。结果:合成了目标化合物V。结论:对目标化合物V用元素分析( PE 2400)、红外光谱(IR)、核磁共振氢谱(1 HNMR)、进行结构表征,分析证实所合成的化合物与预期结构一致。

  9. Synthesis and characterization of Sinomenine-azo-toluene%青藤碱偶氮甲苯的合成与表征

    Institute of Scientific and Technical Information of China (English)

    李勇; 林红卫; 朱士龙; 陈迪钊; 欧阳玉祝


    Sinomenine-azo-toluene has been synthesized using hydrochloric sinomenine and p-aminotoluene as material by diazotizing and coupling reaction. Sinomenine-azo-toluene was named l-(p-toluene azo)-7,8-didehydro-4-hydroxy-3,7-dim-ethoxy-17-methylmorphinan-6-one by the systematic nomenclature. The effects of raw material ratio, reaction temperature , reaction time and pH on the yield of product were investigated. The experimental results showed that under the condition of raw material ratio, reaction temperature,reaction time and pH being 1.1:1 ( mol/mol) ,0 ~ 5 ℃ ,7 and 4 h relatively, the yield and the purity of Sinomenine-azo-toluene could reach to 76. 57% and 96. 25% . The structure of product was confirmed by UV,IR, 1HNMR and MS characterization.%以盐酸青藤碱和对甲苯胺为原料,通过重氮化、偶合反应制得青藤碱偶氮甲苯,即1-(对甲苯偶氮基)-7,8-二去氢-4-羟基-3,7-二甲氧基-17-甲基-9α,13α,14α-吗啡烷-6-酮,考察了原料配比、反应温度、反应时间和pH对产物收率的影响.实验结果表明:在原料配比n(盐酸青藤碱)∶n(对甲苯胺)为1.1∶1( mol/mol),温度为0~5℃,pH为7,反应时间4h条件下,产物的总收率76.57%,纯度96.25%.产物经UV、IR、1HNMR和MS表征为目标产物.