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heterocyclic amines

Gunnar Hall, Susanne Alenljung, Ulla Forsgren-Brusk
PURPOSE: The purpose of this study was to identify key odorants in used disposable absorbent incontinence products. DESIGN: Descriptive in vitro study SUBJECTS AND SETTING:: Samples of used incontinence products were collected from 8 residents with urinary incontinence living in geriatric nursing homes in the Gothenburg area of Sweden. Products were chosen from a larger set of products that had previously been characterized by descriptive odor analysis. METHODS: Pieces of the used incontinence products were cut from the wet area, placed in glass bottles, and kept frozen until dynamic headspace sampling of volatile compounds was completed...
March 22, 2017: Journal of Wound, Ostomy, and Continence Nursing
Emilia S Streng, Darren S Lee, Michael W George, Martyn Poliakoff
The use of γ-Al2O3 as a heterogeneous catalyst in scCO2 has been successfully applied to the amination of alcohols for the synthesis of N-alkylated heterocycles. The optimal reaction conditions (temperature and substrate flow rate) were determined using an automated self-optimising reactor, resulting in moderate to high yields of the target products. Carrying out the reaction in scCO2 was shown to be beneficial, as higher yields were obtained in the presence of CO2 than in its absence. A surprising discovery is that, in addition to cyclic amines, cyclic ureas and urethanes could be synthesised by incorporation of CO2 from the supercritical solvent into the product...
2017: Beilstein Journal of Organic Chemistry
Weiqian David Hong, Peter D Gibbons, Suet C Leung, Richard Amewu, Paul A Stocks, Andrew Valentine Stachulski, Pedro C Horta, Maria Lurdes Santos Cristiano, Alison E Shone, Darren Moss, Alison Ardrey, Raman Sharma, Ashley J Warman, Paul T P Bedingfield, Nicholas E Fisher, Ghaith Aljayyoussi, Sally Mead, Maxine Caws, Neil G Berry, Stephen A Ward, Giancarlo A Biagini, Paul M O'Neill, Gemma Louise Nixon
A High-throughput screen (HTS) was undertaken against the respiratory chain dehydrogenase component, NADH:menaquinone oxidoreductase (Ndh) of Mycobacterium tuberculosis (Mtb). 11,000 compounds were selected for the HTS based on the known phenothiazine Ndh inhibitors, trifluoperazine and thioridazine. Combined HTS (11,000 compounds) and in-house screening of a limited number of quinolones (50 compounds) identified ~100 hits and four distinct chemotypes, the most promising of which contained the quinolone core...
March 17, 2017: Journal of Medicinal Chemistry
Jin Hu, Linlin Ma, Huiqiang Wang, Haiyan Yan, Dajun Zhang, Zhuorong Li, Jiandong Jiang, Yuhuan Li
BACKGROUD: Influenza virus is still a huge threat to the world-wide public health. Host inosine-5'- monophosphate dehydrogenase (IMPDH) involved in the synthesis of guanine nucleotides, is known to be a potential target to inhibit the replication of viruses. Herein, we evaluated antiviral activity of a benzo-heterocyclic amine derivative N30, which was designed to inhibit IMPDH. RESULTS: The results demonstrated that N30 inhibited the replication of H1N1, H3N2, influenza B viruses, including oseltamivir and amantadine resistant strains in vitro...
March 15, 2017: Virology Journal
Bidraha Bagh, Daniël L J Broere, Vivek Sinha, Petrus F Kuijpers, Nicolaas van Leest, Bas de Bruin, Serhiy Demeshko, Maxime A Siegler, Jarl Ivar van der Vlugt
Coordination of FeCl3 to the redox-active pyridine-aminophenol ligand NNOH2 in the presence of base and under aerobic conditions generates FeCl2(NNOISQ) (1), featuring high spin FeIII and an NNOISQ radical ligand. The complex has an overall S = 2 spin state, as deduced from experimental and computational data. The ligand-centered radical couples anti-ferromagnetically with the Fe center. Readily available, well-defined and air-stable 1 catalyzes the challenging intramolecular direct C(sp3)-H amination of unactivated organic azides to generate a range of saturated N-heterocycles with the highest TON (1 mol% 1, 12 h, TON = 62; 0...
March 15, 2017: Journal of the American Chemical Society
Ying-Shiuan Chen, Rong Wang, Wan-Mohaiza Dashwood, Christiane V Löhr, David E Williams, Emily Ho, Susanne Mertens-Talcott, Roderick H Dashwood
Heterocyclic amines (HCAs) produced during high-temperature cooking have been studied extensively in terms of their genotoxic/genetic effects, but recent work has implicated epigenetic mechanisms involving non-coding RNAs. Colon tumors induced in the rat by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) have altered microRNA (miRNA) signatures linked to dysregulated pluripotency factors, such as c-Myc and Krüppel-like factor 4 (KLF4). We tested the hypothesis that dysregulated miRNAs from PhIP-induced colon tumors would provide a "PhIP signature" for use in other target organs obtained from a 1-year carcinogenicity bioassay in the rat...
March 13, 2017: Archives of Toxicology
Zahra Ebrahimpour, Mehdi Bakavoli, Ali Shiri, Seyed Mohammad Seyedi, Tayebe Asghari, Joel T Mague
Derivatives of a new heterocyclic system, pyrimido[5,4-e]thiazolo[3,2-a]pyrimidine 3, were prepared by sequential treatment of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate 1 with 4,5-dihydrothiazol-2-amine 2 and various secondary amines. Single crystal X-ray analysis confirmed the structure of the regioisomer 3. The photophysical characterization of these new compounds was performed by UV/VIS absorption and fluorescence emission spectroscopy. Out of six derivatives studied, only four products 4a-d showed relatively strong fluorescence intensity...
March 10, 2017: Journal of Fluorescence
Julian Freedland, Cinzia Cera, Michael Fasullo
CYP1A1 functions in detoxifying xenobiotics but occasionally converts compounds into potent genotoxins. CYP1A1 activates polyaromatic hydrocarbons, such as benzo[a]pyrene 7,8 dihydrodiol (BaP-DHD), rendering them genotoxic. Particular alleles of CYP1A1, such as CYP1A1 I462V have been correlated with a higher incidence of breast and lung cancer, but it is unknown whether these variants express enzymes in vivo that are more potent in generating genotoxins. We individually expressed CYP1A1 (CYP1A1.1), CYP1A1 T461N (CYP1A1...
March 2017: Mutation Research
Pankaj Jain, Pritha Verma, Guoqin Xia, Jin-Quan Yu
Saturated aza-heterocycles are highly privileged building blocks that are commonly encountered in bioactive compounds and approved therapeutic agents. These N-heterocycles are also incorporated as chiral auxiliaries and ligands in asymmetric synthesis. As such, the development of methods to functionalize the α-methylene C-H bonds of these systems enantioselectively is of great importance, especially in drug discovery. Currently, enantioselective lithiation with (-)-sparteine followed by Pd(0) catalysed cross-coupling to prepare α-arylated amines is largely limited to pyrrolidines...
February 2017: Nature Chemistry
Pavan Mandapati, Patrick K Giesbrecht, Rebecca L Davis, David E Herbert
Proligands based on bis(8-quinolinyl)amine (L1) were prepared containing one (L2) and two (L3) benzo-fused N-heterocyclic phenanthridinyl (3,4-benzoquinolinyl) units. Taken as a series, L1-L3 provides a ligand template for exploring systematic π-extension in the context of tridentate pincer-like amido complexes of group 10 metals (1-M, 2-M, and 3-M; M = Ni, Pd, Pt). Inclusion of phenanthridinyl units was enabled by development of a cross-coupling/condensation route to 6-unsubstituted, 4-substituted phenanthridines (4-Br, 4-NO2, 4-NH2) suitable for elaboration into the target ligand frameworks...
March 7, 2017: Inorganic Chemistry
Ai-Fang Wang, Peng Zhou, Yi-Long Zhu, Wen-Juan Hao, Guigen Li, Shu-Jiang Tu, Bo Jiang
A novel I2-mediated benzannulation of 1,7-diyne-involved 1,4-oxo-migration was established, providing a range of unexpected 1-aroyl-2-naphthaldehydes with a 1,4-dicarbonyl unit. The resulting 1-aroyl-2-naphthaldehydes were successfully applied in the synthesis of benzo[e]isoindol-3-ones and benzo[e]benzo[4,5]imidazo[2,1-a]isoindoles using aromatic amines and benzene-1,2-diamines as nucleophiles, respectively. The mechanisms for the formation of these compounds were proposed.
March 7, 2017: Chemical Communications: Chem Comm
Xiao-Bing Lan, Yinwu Li, Yan-Fang Li, Dong-Sheng Shen, Zhuofeng Ke, Feng-Shou Liu
To achieve efficient palladium-catalyzed cross-coupling reaction under mild reaction conditions with the flexible steric bulk strategy, a series of Pd-PEPPSI (PEPPSI: pyridine-enhanced precatalyst preparation, stabilization, and initiation) complexes C1-C6 were synthesized and characterized, in which unsymmetric flexible steric bulk was introduced on the N-aryl of ancenaphthyl skeleton. These well-defined palladium complexes were found to be excellent precatalysts for Buchwald-Hartwig amination of aryl chlorides with amines in air...
March 6, 2017: Journal of Organic Chemistry
Mikhail Krasavin, Mikhail Korsakov, Zhanna Zvonaryova, Evgenii Semyonychev, Tiziano Tuccinardi, Stanislav Kalinin, Muhammet Tanç, Claudiu T Supuran
Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors...
February 13, 2017: Bioorganic & Medicinal Chemistry
Michael Desanker, Xingliang He, Jie Lu, Pinzhi Liu, David B Pickens, Massimiliano Delferro, Tobin J Marks, Yip-Wah Chung, Q Jane Wang
Modern automotive engines operate at higher power densities than ever before, driving a need for new lubricant additives capable of reducing friction and wear further than ever before while not poisoning the catalytic converter. Reported in this paper is a new class of molecular friction modifier (FM), represented by 1,4,7,10-tetradodecyl-1,4,7,10-tetraazacyclododecane (1a), designed to employ thermally stable, sulfur- and phosphorus-free alkyl-substituted nitrogen heterocycles with multiple nitrogen centers per molecule...
March 2, 2017: ACS Applied Materials & Interfaces
Rong Wang, Ying-Shiuan Chen, Wan-Mohaiza Dashwood, Qingjie Li, Christiane V Löhr, Kay Fischer, Emily Ho, David E Williams, Roderick H Dashwood
The heterocyclic amine 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) targets multiple organs for tumorigenesis in the rat, including the colon and the skin. PhIP-induced skin tumors were subjected to mutation screening, which identified genetic changes in Hras (7/40, 17.5%) and Tp53 (2/40, 5%), but not in Ctnnb1, a commonly mutated gene in PhIP-induced colon tumors. Despite the absence of Ctnnb1 mutations, β-catenin was overexpressed in nuclear and plasma membrane fractions from PhIP-induced skin tumors, coinciding with loss of p120-catenin from the plasma membrane, and the appearance of multiple p120-catenin-associated bands in the nuclear extracts...
February 20, 2017: Molecular Carcinogenesis
Nancy D Turner, Shannon K Lloyd
A role for red and processed meat in the development of colorectal cancer has been proposed based largely on evidence from observational studies in humans, especially in those populations consuming a westernized diet. Determination of causation specifically by red or processed meat is contingent upon identification of plausible mechanisms that lead to colorectal cancer. We conducted a systematic review of the available evidence to determine the availability of plausible mechanistic data linking red and processed meat consumption to colorectal cancer risk...
January 1, 2017: Experimental Biology and Medicine
Jian Xie, Yue-Wei Wang, Lian-Wen Qi, Bo Zhang
A copper-catalyzed aminooxygenation of unactivated alkenes with various O-nucleophiles is described. This novel methodology uses commercially available N-fluorobenzenesulfonimide as an amination reagent and provides a simple and efficient approach to a wide range of aminated saturated oxygen heterocycles in moderate to good yields. The reaction features mild reaction conditions, operational simplicity, and a broad substrate scope.
February 16, 2017: Organic Letters
Cátia I C Esteves, M Manuela M Raposo, Susana P G Costa
Novel thienyl and bithienyl amino acids with different substituents were obtained by a multicomponent Ugi reaction between a heterocyclic aldehyde, an amine, an acid and an isocyanide. Due to the presence of the sulphur heterocycle at the side chain, these unnatural amino acids are highly emissive and bear extra electron donating atoms so they were tested for their ability to act as fluorescent probes and chemosensors in the recognition of biomedically relevant ions in acetonitrile and acetonitrile/water solutions...
February 14, 2017: Amino Acids
Pan Wang, Yanting Hong, Weixin Ke, Xiaosong Hu, Fang Chen
BACKGROUND: Heterocyclic aromatic amines (HAAs) are one type of neo-formed contaminants in protein-rich foods during heat processing. Recently, accumulative studies have focused on the formation of HAs in Western foods. However, there is little knowledge about the occurrence of HAAs in traditional Chinese foods. The objective of this study was to determinate the contents of main HAs in traditional marinated meat products by UPLC-MS/MS, and to investigate the effects of animal species and the ingredients (soy sauce, rock candy, and rice wine) on the formation of HAAs in marinated meats...
February 11, 2017: Journal of the Science of Food and Agriculture
Christiana Iwuagwu, Dalton King, Ivar M McDonald, James Cook, F Christopher Zusi, Matthew D Hill, Robert A Mate, Haiquan Fang, Ronald Knox, Lizbeth Gallagher, Debra Post-Munson Amy Easton, Regina Miller, Yulia Benitex, Judy Siuciak, Nicholas Lodge, Robert Zaczek, Daniel Morgan, Linda Bristow, John E Macor, Richard E Olson
Quinuclidine-containing spirooxazolines, as described in the previous report in this series, were demonstrated to have utility as α7 nicotinic acetylcholine receptor (α7 nAChR) partial agonists. In this work, the SAR of this chemotype was expanded to include an array of diazine heterocyclic substitutions. Many of the heterocyclic analogs were potent partial agonists of the α7 receptor, selective against other nicotinic receptors and the serotinergic 5HT3A receptor. (1'S,3'R,4'S)-N-(6-phenylpyrimidin-4-yl)-4H-1'-azaspiro[oxazole-5,3'-bicyclo[2...
January 20, 2017: Bioorganic & Medicinal Chemistry Letters
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