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heterocyclic amines

Arunan Jeyakumar, Lakal Dissabandara, Vinod Gopalan
A recent investigation by the World Health Organisation (WHO) has found that the consumption of processed meat and potentially red meat promotes carcinogenesis and can increase the risk of colorectal cancer. This literature review aims to summarise both the red and processed meat molecules associated with colorectal carcinogenesis and investigate their relationship with the pathogenic process of colorectal cancer. Literature relating to the carcinogenic effect of red and processed meat molecules was critically reviewed...
December 2, 2016: Journal of Gastroenterology
Lijun Fan, Christopher P Davie
DNA-encoded library technology (ELT) has spurred wide interest in the pharmaceutical industry as a powerful tool for hit and lead generation. In recent years a number of "DNA-compatible" chemical modifications have been published and used to synthesize vastly diverse screening libraries. Herein we report a newly developed, zirconium tetrakis(dodecyl sulfate) [Zr(DS)4] catalyzed ring-opening of on-DNA epoxides in water with amines, including anilines. Subsequent cyclization of the resulting on-DNA β-amino alcohols leads to a variety of biologically interesting, non-aromatic heterocycles...
November 30, 2016: Chembiochem: a European Journal of Chemical Biology
Lili Wang, Xin He, Chunhuan Jin, Gregory Ondieki
The adverse reactions and side effects associated with use of herbal medicines, especially their damaging effects on the liver have increasingly been reported worldwide. Some of the herbal ingredients have the potential risk of herb-induced liver injury but their hepatotoxicity mechanisms and associated risk factors are not well characterized until now. Xenobiotics are catalyzed by cytochrome P450 enzymes into highly reactive metabolites, which can covalently bind to the enzyme itself and subsequently cause mechanism-based inhibition (MBI)...
November 23, 2016: Current Drug Metabolism
Daniela Vullo, Sonia Del Prete, Sameh M Osman, Zeid AlOthman, Clemente Capasso, William A Donald, Claudiu T Supuran
Activation of the γ-class carbonic anhydrase (CAs, EC from the pathogenic bacterium Burkholderia pseudomallei (BpsγCA) with a series of natural and non-natural amino acids and aromatic/heterocyclic amines has been investigated. The best BpsγCA activators were d-His, l-DOPA, d-Trp, 4-amino-l-Phe, dopamine, 2-(2-aminoethyl)pyridine, 2-aminoethyl-piparazine/morpholine and l-adrenaline, which showed activation constants ranging between 9 and 86nM. The least effective activators were l-His, l-Phe and 2-pyridyl-methylamine, with KAs in the range of 1...
November 12, 2016: Bioorganic & Medicinal Chemistry Letters
Javier García-Lomillo, Olga Viegas, Maria L Gonzalez-SanJose, Isabel M P L V O Ferreira
Polycyclic aromatic hydrocarbons (PAHs) and heterocyclic aromatic amines (HAs) are carcinogenic compounds formed in barbecued meat. Conditions that reduce their formation are of major interest. This study aims to evaluate the influence of red wine pomace seasoning (RWPS) and high-oxygen atmosphere storage on the formation of PAHs and HAs in barbecued beef patties. In general, the levels of PAHs and HAs quantified were low. The storage (9days) promoted higher formation of PAHs in control patties without increase of HAs...
November 15, 2016: Meat Science
David Ventura-Espinosa, Aida Marzá-Beltrán, Jose A Mata
The potential application of the primary amine/nitrile pair as a liquid organic hydrogen carrier (LOHC) has been evaluated. Ruthenium complexes of formula [(p-cym)Ru(NHC)Cl2 ] (NHC=N-heterocyclic carbene) catalyze the acceptorless dehydrogenation of primary amines to nitriles with the formation of molecular hydrogen. Notably, the reaction proceeds without any external additive, under air, and under mild reaction conditions. The catalytic properties of a ruthenium complex supported on the surface of graphene have been explored for reutilization purposes...
November 10, 2016: Chemistry: a European Journal
Xi Liu, Mei-Yan Wang, Si-Yuan Wang, Qi Wang, Liang-Nian He
Incorporation of CO2 into heterocycle compounds i.e. 2-oxazolidinones under mild conditions, especially at atmospheric pressure still remains challenging. The mononuclear zinc(II) complex viz. ZnCl2(TBD)2 in this study was for the first time demonstrated as a robust catalyst for the carboxylative cyclization of propargylic amines with CO2 to exclusively afford various 2-oxazolidinones in excellent yields. Notably, the zinc(II) catalytic species is readily in situ generated from zinc dichloride and 1,5,7-triazabicyclo[4...
November 8, 2016: ChemSusChem
Ai-Jun Ding, Gui-Sheng Wu, Bin Tang, Xuechuan Hong, Michael X Zhu, Huai-Rong Luo
With the growth of aging population, there is increasing demand to develop strategy to improve the aging process and aging-related diseases. Benzimidazole and its derivatives are crucial heterocyclic backbone of many drugs and compounds with diverse therapeutic applications, including alleviation of aging-related diseases. Here, we investigate if the benzimidazole derivative n-butyl-[1H]-benzimidazol-2-amine (M084), a novel inhibitor of TRPC4 and TRPC5 channels and antidepressant, could affect the lifespan of Caenorhabditis elegans (C...
November 16, 2016: Molecular and Cellular Biochemistry
Chao Liu, Huiyan Zhang, Rui Xiao, Shubin Wu
Thermogravimetric characteristics of chitin and chitosan and their potentials to produce value-added organonitrogen chemicals were separately evaluated via TG/DSC-FTIR and Py-GC/MS. Results shown that chitin had the better thermal stability and higher activation energy than chitosan because of the abundant acetamido group. Furthermore, the dominated volatilization in active pyrolysis of chitin contributed to its endothermic property, whereas the charring in chitosan led to the exothermal. During fast pyrolysis, the acetamido group in chitin and chitosan was converted into acetic acid or acetamide...
January 20, 2017: Carbohydrate Polymers
Katelynn M Mason, Michael S Meyers, Abbie M Fox, Sarah B Luesse
Efficient one-pot Ugi-Smiles couplings are reported for the use of furyl-substituted aldehyde components. In the presence of these heterocyclic aldehydes, reactions tolerated variations in amine components and led to either isolated N-arylamide Ugi-Smiles adducts or N-arylepoxyisoindolines, products of tandem Ugi-Smiles Diels-Alder cyclizations, in moderate yields. A thienyl-substituted aldehyde was also a competent component for Ugi-Smiles adduct formation.
2016: Beilstein Journal of Organic Chemistry
Christina Engels, Clarissa Schwab, Jianbo Zhang, Marc J A Stevens, Corinne Bieri, Marc-Olivier Ebert, Kristopher McNeill, Shana J Sturla, Christophe Lacroix
Glycerol/diol dehydratases catalyze the conversion of glycerol to 3-hydroxypropionaldehyde (3-HPA), the basis of a multi-component system called reuterin. Reuterin has antimicrobial properties and undergoes chemical conjugation with dietary heterocyclic amines (HCAs). In aqueous solution reuterin is in dynamic equilibrium with the toxicant acrolein. It was the aim of this study to investigate the extent of acrolein formation at various physiological conditions and to determine its role in biological and chemical activities...
November 7, 2016: Scientific Reports
Medjda Bellamri, Ludovic Le Hegarat, Laurent Vernhet, Georges Baffet, Robert J Turesky, Sophie Langouët
Heterocyclic aromatic amines (HAA) are formed in cooked meat, poultry and fish but also arise in tobacco smoke and exhaust gases. HAA are potential human carcinogens, which require metabolic activation to exert their genotoxicity. Human tissues can bioactivate HAA to produce reactive intermediates that bind to DNA. HAA DNA adduct formation occurs in human hepatocytes; however, the potential of HAA to form DNA adducts has not been investigated in human T lymphocytes. In this study, we investigated the ability of human T lymphocytes activated with PMA/Ionomycin or CD3/CD28 to express functional CYP1 activity and bioactivate three major HAA: 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), and 2-amino-9H-pyrido[2,3-b]indole (AαC) to form DNA adducts...
December 2016: Environmental and Molecular Mutagenesis
Yongwei Wu, Yan-Qiao Chen, Tao Liu, Martin Eastgate, Jin-Quan Yu
Pd(II)-catalyzed γ-C(sp(3))-H arylation of primary amines is realized by using 2-hydroxynicotinaldehyde as a catalytic transient directing group. Importantly, the catalyst and the directing group loading can be lowered to 2% and 4% respectively, thus demonstrating high efficiency of this newly designed transient directing group. Heterocyclic aryl iodides are also compatible with this reaction. Furthermore, swift synthesis of 1,2,3,4-tetrahydronaphthyridine derivatives is accomplished using this reaction.
October 27, 2016: Journal of the American Chemical Society
Lixin Li, Peipei Liu, Yijin Su, Hanmin Huang
Thanks to the facile imine-enamine tautomerization, the β,γ-unsaturated hydrazones have been successfully utilized as surrogates of aminodienes for realizing the Pd-catalyzed tandem aminomethylamination/aromatization reaction with aminals via C-N bond activation. This direct and operationally simple protocol provides a fundamentally novel strategy to synthesize aromatic heterocycles from alkenes in the absence of external oxidant and base. Mechanistic studies suggested that aminal not only functioned as an aminomethyl source but also acted as formal oxidant and inner base to promote the aromatization...
October 26, 2016: Organic Letters
Abdul Hameed, Mariya Al-Rashida, Maliha Uroos, Syed Ali, Khalid M Khan
Schiff bases are synthetically accessible and structurally diverse compounds, typically obtained by facile condensation between an aldehyde, or a ketone with primary amines. Schiff bases contain an azomethine (-C=N-) linkage that stitches together two or more biologically active aromatic/heterocyclic scaffolds to form various molecular hybrids with interesting biological properties. Schiff bases are versatile metal complexing agents and have been known to coordinate all metals to form stable metal complexes with vast therapeutic applications...
October 24, 2016: Expert Opinion on Therapeutic Patents
S El-Meligie, Azza T Taher, Aliaa M Kamal, A Youssef
A series of chalcone analogous compounds were designed and synthesized. Replacing/substituting the enone or ethylenic bridge of the parent chalcone with rigid heterocyclic moieties or substituted aromatic amines gave nineteen target compounds. Their cytotoxic activities were screened against both breast and liver cancer cells as well as breast and liver normal cells. Target compounds were also evaluated for their inhibition activity of tubulin beta polymerization. Target compound 2e, 3a, 3b, 3c, 4a-4d, 5a, 5b and 6 showed broad spectrum excellent anticancer activity against both MCF-7 and HepG2...
October 1, 2016: European Journal of Medicinal Chemistry
Xiao-Lan Xu, Wen-Tao Xu, Ji-Wei Wu, Jian-Bo He, Hua-Jian Xu
A general and effective method for the synthesis of amides through decarboxylative amidation of α-keto acids with amines has been developed. The reaction proceeded smoothly to afford the corresponding amide products in good yield under air and shows excellent functional group tolerance. In addition, the protocol can be further applied in the synthesis of heterocyclic compounds like benzimidazoles.
October 7, 2016: Organic & Biomolecular Chemistry
Peng Wang, Gen-Cheng Li, Pankaj Jain, Marcus E Farmer, Jian He, Peng-Xiang Shen, Jin-Quan Yu
Meta-C-H amination and meta-C-H alkynylation using a modified norbornene (methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate) as a transient mediator has been developed for the first time. Both the identification of a mono-protected 3-amino-2-hydroxypyridine/pyridone type ligand and the use of methyl bicyclo[2.2.1]hept-2-ene-2-carboxylate as the mediator are crucial for realizing these two unprecedented meta-C-H transformations. A variety of substrates are compatible with both meta-C-H amination and meta-C-H alkynylation...
October 7, 2016: Journal of the American Chemical Society
Pengyuan Ding, Libing Chu, Jianlong Wang
A novel process integrating anaerobic hydrolysis-acidification (HA) and anoxic/oxic (A/O) reactors was developed to treat the actual petrochemical wastewater, which was operated for more than 8 months, the removal efficiency of COD and NH4(+)-N was monitored, and the microbial community was analyzed. The results showed that the effluent concentrations were maintained at around 99 and 1.3 mg/L, with the removal efficiency of 70.6 and 95.4 %, respectively at a total hydraulic retention time (HRT) of 20 h...
October 5, 2016: Applied Microbiology and Biotechnology
Wan-Yun Huang, Shaik Anwar, Kwunmin Chen
The Morita-Baylis-Hillman (MBH) reaction is one of the most useful and efficient protocols for constructing new carbon-carbon bonds between an activated olefin and electrophiles in the presence of a tertiary amine/phosphine. Herein, we present the use of MBH alcohols, which are obtained from the reaction of nitrostyrenes with aldehydes, as well as acetates and amines derived thereof in several organocatalytic transformations. Densely functionalised MBH adducts can also be used to synthesise substituted heteroaromatic compounds, such as furan, pyrrole, pyrazole and imidazole derivatives...
October 4, 2016: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
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