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heterocyclic amines

Francisco Lopez-Tapia, Christine Brotherton-Pleiss, Peibin Yue, Heide Murakami, Ana Carolina Costa Araujo, Bruna Reis Dos Santos, Erin Ichinotsubo, Anna Rabkin, Raj Shah, Megan Lantz, Suzie Chen, Marcus A Tius, James Turkson
The molecular determinants for the activities of the reported benzoic acid (SH4-54), salicylic acid (BP-1-102), and benzohydroxamic acid (SH5-07)-based STAT3 inhibitors were investigated to design optimized analogues. All three leads are based on an N -methylglycinamide scaffold, with its two amine groups condensed with three different functionalities. The three functionalities and the CH2 group of the glycinamide scaffold were separately modified. The replacement of the pentafluorobenzene or cyclohexylbenzene, or replacing the benzene ring of the aromatic carboxylic or hydroxamic acid motif with heterocyclic components (containing nitrogen and oxygen elements) all decreased potency...
March 8, 2018: ACS Medicinal Chemistry Letters
Mahmoud Nasrollahzadeh, Mohaddeseh Sajjadi, Fatemeh Ghorbannezhad, S Mohammad Sajadi
A3 coupling is one of the few transition-metal catalyzed carbon-carbon bond forming reactions that have been established as a most direct, efficient and atom-economical synthetic approach to afford propargylamine derivatives using various catalysts. A large number of nanosized heterogeneous catalysts for three-component coupling reactions between an aldehyde, an amine, and a terminal alkyne have been popularly introduced as an A3 coupling in the last decade. The coupling product has found a broad application as a key intermediate for a variety of heterocyclic useful compounds and numerous biologically active molecules such as β-lactams, conformationally restricted peptides, isosteres, herbicides, fungicides, indolizines, pyrroles, quinolines and therapeutic drug molecules...
March 14, 2018: Chemical Record: An Official Publication of the Chemical Society of Japan ... [et Al.]
Gangam Srikanth Kumar, Diksha Singh, Manish Kumar, Manmohan Kapur
We report herein, an unprecedented and expedient Pd-catalyzed oxidative coupling of allyl alcohols with anilines to afford β-amino ketones which are converted into substituted quinolines in a one-pot fashion. The exclusive preference for N-alkylation over N-allylation makes this approach unique, when compared to those reported in literature. Detailed mechanistic investigations reveal that the conjugate addition pathway was the predominant one over the allylic amination pathway. The notable aspects of the present approach are the use of readily available, bench-stable, allyl alcohols and molecular oxygen as the terminal oxidant, in the process dispensing the need for unstable and costly enones...
March 13, 2018: Journal of Organic Chemistry
Gang Liu, Geng Zong, Kana Wu, Yang Hu, Yanping Li, Walter C Willett, David M Eisenberg, Frank B Hu, Qi Sun
OBJECTIVE: To examine open-flame and/or high-temperature cooking (grilling/barbecuing, broiling, or roasting) and doneness preferences (rare, medium, or well done) for red meat, chicken, and fish in relation to type 2 diabetes (T2D) risk among U.S. adults who consumed animal flesh regularly (≥2 servings/week). RESEARCH DESIGN AND METHODS: The prospective studies included 52,752 women from the Nurses' Health Study (NHS, followed during 1996-2012), 60,809 women from NHS II (followed during 2001-2013), and 24,679 men from the Health Professionals Follow-up Study (HPFS, followed during 1996-2012) who were free of diabetes, cardiovascular disease, and cancer at baseline...
March 12, 2018: Diabetes Care
Rui-Qi Li, Yu He, Yao Ding, Chee-Kiat Ang, Jie-Sheng Tian, Teck-Peng Loh
A concise two-step operation of α-amination of aldehydes and subsequent Friedel-Crafts/Prins-type cyclization towards accessing tetrahydrobenzo[c]phenanthridine and related structures was developed. The reaction displayed a broad substrate scope and good tolerance to a variety of substituents such as different aromatic heterocyclic rings. In addition, the effectiveness of this protocol was also demonstrated in the formal synthesis of homochelidonine and chelamidine.
March 12, 2018: Chemical Communications: Chem Comm
Vitaliy M Sviripa, Liliia M Kril, Wen Zhang, Yanqi Xie, Przemyslaw Wyrebek, Larissa Ponomareva, Xifu Liu, Yaxia Yuan, Chang-Guo Zhan, David S Watt, Chunming Liu
Fluorinated, phenylethynyl-substituted heterocycles that possessed either an N -methylamino or N,N -dimethylamino group attached to heterocycles including pyridines, indoles, 1 H -indazoles, quinolines, and isoquinolines inhibited the proliferation of LS174T colon cancer cells in which the inhibition of cyclin D1 and induction of the cyclin-dependent kinase inhibitor-1 ( i.e ., p21Wif1/Cip1 ) served as a readout for antineoplastic activity at a cellular level. On a molecular level, these agents, particularly 4-((2,6-difluorophenyl)ethynyl)- N -methylisoquinolin-1-amine and 4-((2,6-difluorophenyl)ethynyl)- N , N -dimethylisoquinolin-1-amine, bound and inhibited the catalytic subunit of methionine S-adenosyltransferase-2 (MAT2A)...
2018: MedChemComm
Mushtaq Ahmad, Zahida Perveen, Adailton J Bortoluzzi, Shahid Hameed, Muhammad R Shah, Muhammad Tariq, Ghias Ud Din, Muhammad T Jan, Muhammad Siddique, Muhammad Anwar
Apart from its numerous biological activities like antidiabetic, anti-inflammatory, antimicrobial, pyrazine moiety plays an important role in luminescent materials. Its role in luminescent materials is due to its highly electron deficient nature specially when it is in the centre along the mainstay of extended π-conjugated systems. Similarly, new liquid crystalline compounds are being made constantly where the central benzoaromatic moiety is being replaced with the heterocycles including pyrazine due to their more variable nature...
March 8, 2018: Chemistry Central Journal
Eman M Mohi El-Deen, Eman K Abd El-Hameed
Synthesis of a series of novel 10-substituted-pyrido[3',2':4,5]thieno[3,2-b] quinoline derivatives 3-15, which contain a planar tetracyclic heteroring system, has been accomplished. The synthetic approaches for the target compounds included, condensation reaction of 10-amino derivatives 2 with triethyl orthoformate to give ethyl N-formimidate derivatives 3, which in turn reacted with different amines to give N-substituted formimidamide derivatives 4a,b. In addition, N-mustard derivative 6 was synthesized via treatment of 2,2'- azanediylbis(ethan-1-ol) derivative 5 with thionyl chloride...
May 2017: Acta Poloniae Pharmaceutica
Jerry D Monroe, Heidi L Hruska, Hannah K Ruggles, Kevin M Williams, Michael E Smith
Unlike cisplatin, which forms bifunctional DNA adducts, monofunctional platinum(II) complexes bind only one strand of DNA and might target cancer without causing auditory side-effects associated with cisplatin treatment. We synthesized the monofunctional triamine-ligated platinum(II) complexes, Pt(diethylenetriamine)Cl, [Pt(dien)Cl]+, and Pt(N,N-diethyldiethylenetriamine)Cl, [Pt(Et2dien)Cl]+, and the monofunctional heterocyclic-ligated platinum(II) complexes, pyriplatin and phenanthriplatin, and compared their 5'-GMP binding rates, cellular compartmental distribution and cellular viability effects...
2018: PloS One
Qiqi Wang, Lianpeng Zhang, Jinzhong Yao, Guanyinsheng Qiu, Xiaofang Li, Hongwei Zhou
Silver-catalyzed stereoselective synthesis of polysubstituted (Z)-1,2-dihydrobenzo[cd]indoles from 8-ethynylnaphthalen-1-amines is reported. In this protocol, a series of nitrogen-containing heterocyclic compounds were synthesized by silver-catalyzed α-addition of alkyne bond with high selectivity and high yields. The synthesized polysubstituted 1,2-dihydrobenzo[cd]indoles could be easily converted to benzo[cd]indol-2(1H)-ones, and both 1,2-dihydrobenzo[cd]indoles and benzo[cd]indol- 2(1H)-ones are biological and pharmaceutical cores...
March 6, 2018: Journal of Organic Chemistry
Kazuyuki Tokumaru, Kalisankar Bera, Jeffrey N Johnston
Umpolung Amide Synthesis (UmAS) has emerged as a superior alternative to conventional amide synthesis methods based on carbonyl electrophiles in a range of situations, particularly when epimerization-prone couplings are prescribed. In an unanticipated development during our most recent studies, it was discovered that diacyl hydrazide products from UmAS were not formed as intermediates when using an acyl hydrazide as the amine acceptor. This resulted in a new preparation of 1,3,4-oxadiazoles from α-bromonitroalkane donors...
October 2017: Synthesis
Huan-Ming Huang, Joseph McDouall, David John Procter
Radical anions generated from urea carbonyls by reductive electron transfer are exploited in carbon-carbon bond formation. New radical cyclizations of urea radical anions deliver complex nitrogen heterocycles and, depending upon the proton source used in the reactions, a chemoselective switch between reaction pathways can deliver two heterobicyclic scaffolds. A computational study has been used to investigate the selectivity of the urea radical processes. Furthermore, radical cyclization cascades involving urea radical anions deliver unusual spirocyclic aminal architectures...
March 1, 2018: Angewandte Chemie
Yoichi Kadoh, Haruko Miyoshi, Takehiko Matsumura, Yoshihito Tanaka, Mitsuya Hongu, Mayumi Kimura, Kei Takedomi, Kenji Omori, Jun Kotera, Takashi Sasaki, Tamaki Kobayashi, Hiroyuki Taniguchi, Yumi Watanabe, Koki Kojima, Toshiaki Sakamoto, Toshiyuki Himiyama, Eiji Kawanishi
Phosphodiesterase (PDE) 10A is a dual hydrolase of cAMP and cGMP and highly expressed in striatal medium spiny neurons. Inhibition of PDE10A modulates the activity of medium spiny neurons (MSN) via the regulation of cAMP and cGMP. Signal control of MSN is considered associated with psychotic symptoms. Therefore PDE10A inhibitor is expected as a therapeutic method for psychosis disease such as schizophrenia. Avanafil (1) is a PDE5 inhibitor (treatment for erectile dysfunction) discovered by our company. We paid attention to the homology of PDE10A and PDE5 and took advantage of PDE5 inhibitor library to discover PDE10A inhibitors, and found a series of compounds that exhibit higher potency for PDE10A than PDE5...
2018: Chemical & Pharmaceutical Bulletin
Fatemeh Abedini, Reza Omidyan
Thiazolo-[4, 5-d]-Thiazo-frame (tztz) compounds are important hetero-aromatic organic-systems, which recently become subject of several studies in the field of organic electronics and organic photovoltaics (OPVs). The most important physical nature of these systems is reported to be an equilibrium between enol-keto forms following excited state proton transfer. This process originates from a flat trend of the S1 PE profile along the PT coordinate. In present work, we have determined and interpreted the excited state proton transfer and photophysical nature of these systems extensively by means of the MP2/CC2 and CASSCF theoretical approaches...
February 28, 2018: Journal of Physical Chemistry. A
Taotao Lu, Zhiming Liu, Carlos A Steren, Fan Fei, Tabitha M Cook, Xue-Tai Chen, Zi-Ling Xue
A series of Ni(ii), Pd(ii) and Pt(ii) complexes [ML][PF6 ]2 [L = L1 , M = Ni (1), Pd (2), Pt (3); L = L2 , M = Ni (4), Pd (5), Pt (6)] and [Pt(L2 )(acac)] (7) have been prepared by the reactions of two tetradentate macrocyclic amine-NHC ligand precursors, [H2 L1 ][PF6 ]2 and [H2 L2 ][PF6 ]2 , with Ni(OAc)2 ·4H2 O, Pd(OAc)2 and Pt(acac)2 in the presence of NaOAc. Complex 7 is isolated along with 6 from the same reaction between [H2 L2 ][PF6 ]2 and Pt(acac)2 . There are two atropisomers in 1-3 and two achiral conformers in 4-6...
February 28, 2018: Dalton Transactions: An International Journal of Inorganic Chemistry
Vinod Vijayan, Avik Mazumder
Cinnamon (Cinnamomum cassia) is an important spice which is widely consumed in the Indian subcontinent as well as in several other parts of the world. In the present study, NMR spectroscopy showed the presence of cinnamaldehyde to be the major component of the bark. The possible mutagenic effects of cinnamon bark ethanolic extract (CEE, 0.01-1 mg/plate) cinnamon oil (CNO, 0.125-1 mg/plate), and its active component cinnamadehyde (CLD, 0.125-1 mg/plate) were evaluated. Antimutagenic activity of CEE, CNO, and CLD was also tested against various food borne mutagens (heterocyclic amines and aflatoxin B1 (AFB1)) and sodium azide (SA) using Ames assay...
February 26, 2018: Drug and Chemical Toxicology
Xiaocun Lu, Joshua S Katz, Adam Schmitt, Jeffrey S Moore
Compartmentalized structures widely exist in cellular systems (organelles) and perform essential functions in smart composite materials (microcapsules, vasculatures, and micelles) to provide localized functionality and enhance materials compatibility. An entirely water-free compartmentalization system is of significant value to the materials community as nonaqueous conditions are critical to packaging microcapsules with water-free hydrophilic payloads while avoiding energy-intensive drying steps. Few nonaqueous encapsulation techniques are known, especially when considering just the scalable processes that operate in batch mode...
February 19, 2018: Journal of the American Chemical Society
Syifaa A S, S Jinap, Md Jahurul Haque Akanda, Maimunah Sanny, A Khatib
The objective of the study was to determine the effect of different types of soy sauce and marinating time on the formation of heterocyclic amines (HCAs) in roasted chicken. Chicken breast samples were marinated with sweet, salty, light and dark soy sauce at 0, 3, 6 and 12 hours (control treatment was the chicken without marinade). The concentrations of free amino acids, sugars and creatinine were determined before roasting while HCA concentrations were determined after roasting. All types of soy sauce significantly increased (p ≤ 0...
February 15, 2018: Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment
Jane G Pouzou, Solenne Costard, Francisco J Zagmutt
This probabilistic analysis estimated daily dietary exposures of the US population to heterocyclic amines and polycyclic aromatic hydrocarbons from meat and some varieties of bread. Mean concentrations for these foods grouped by cooking method and food form were combined with consumption data from the National Health and Nutritional Examination Survey (NHANES). Mean exposure to HCA2 (PhIP + MeIQx), was 565.3 ng/day (95% CrI: 403.73, 726.88), and to PAH8 (sum of BaP, ChY, BaA, BkF, BbF, DahA, IP, and BghiP), was 634...
February 12, 2018: Food and Chemical Toxicology
Jane G Pouzou, Solenne Costard, Francisco J Zagmutt
Random effect meta-regressions were constructed to estimate concentrations of two heterocyclic amines (HCA) and eight polycyclic aromatic hydrocarbons (PAH) in meat and breads. Eighteen HCA studies and nine PAH studies of food concentration were assembled. Concentration was computed for beef, poultry, pork, and seafood, and bread. Fixed effect predictors included cooking time, form of the food, cooking method, interaction between form and cooking method, temperature at which the food was cooked food, fuel of the flame source, percentage of fat, and other elements...
February 12, 2018: Food and Chemical Toxicology
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