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heterocyclic amines

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https://www.readbyqxmd.com/read/28635286/utilization-of-an-active-site-mutant-receptor-for-the-identification-of-potent-and-selective-atypical-5-ht2c-receptor-agonists
#1
Joseph Carpenter, Ying Wang, Gang Wu, Jianxin Feng, Xiang-Yang Ye, Christian L Morales, Matthias Broekema, Karen A Rossi, Keith J Miller, Brian J Murphy, Ginger Yingzhe Wu, Sarah E Malmstrom, Anthony V Azzara, Philip M Sher, John M Fevig, Andrew Alt, Robert L Bertekap, Mary Jane Cullen, Timothy M Harper, Kimberly A Foster, Chiuwa Emily Luk, Qian Xiang, Mary F Grubb, Jeffrey A Robl, Dean A Wacker
Agonism of the 5-HT2C receptor represents one of the most well-studied and clinically-proven mechanisms for pharmacological weight reduction. Selectivity over the closely related 5-HT2A and 5-HT2B receptors is critical as their activation has been shown to lead to undesirable side-effects and major safety concerns. In this communication, we report the development of a new screening paradigm which utilizes an active site mutant D134A 5-HT2C receptor to identify atypical agonist structures. We additionally report the discovery and optimization of a novel class of non-basic heterocyclic amide agonists of 5-HT2C...
June 21, 2017: Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/28635251/molecular-adsorbates-switch-on-heterogeneous-catalysis-induction-of-reactivity-by-n-heterocyclic-carbenes
#2
Johannes B Ernst, Christian Schwermann, Gen-Ichi Yokota, Mizuki Tada, Satoshi Muratsugu, Nikos L Doltsinis, Frank Glorius
In here, we report the N-heterocyclic carbene (NHC)-induced activation of an otherwise unreactive Pd/Al2O3 catalyst. Surface analysis techniques demonstrate the NHC being coordinated to the palladium particles and affecting their electronic properties. Fur-thermore, ab initio calculations provide additional insight into the electronic effect of the coordination with the NHC injecting electron density into the metal nanocluster thus lowering the barrier for bromobenzene activation. By this NHC modification, the catalyst could be successfully applied in the Buchwald-Hartwig amination of aryl chlorides, bromides, and iodides...
June 21, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28632937/synthesis-biological-evaluation-and-docking-studies-of-trans-stilbene-methylthio-derivatives-as-cytochromes-p450-family-1-inhibitors
#3
Marcin Wierzchowski, Zbigniew Dutkiewicz, Agnieszka Gielara-Korzańska, Artur Korzański, Anna Teubert, Artur Teżyk, Tomasz Stefański, Wanda Baer-Dubowska, Renata Mikstacka
Cytochromes P450 family 1 (CYP1) are responsible for the metabolism of procarcinogens, e.g. polycyclic aromatic hydrocarbons and aromatic and heterocyclic amines. The inhibition of CYP1 activity is examined in terms of chemoprevention and cancer chemotherapy. We designed and synthesized a series of trans-stilbene derivatives possessing a combination of methoxy and methylthio functional groups attached in different positions to the trans-stilbene skeleton. We determined the effects of synthesized compounds on the activities of human recombinant CYP1A1, CYP1A2 and CYP1B1 and, to explain the variation of inhibitory potency of methoxystilbene derivatives and their methylthio analogs, we employed computational analysis...
June 20, 2017: Chemical Biology & Drug Design
https://www.readbyqxmd.com/read/28631832/synthesis-of-two-carbon-14-analogue-of-thioflavanones
#4
Mohammad Basooti, Naghi Saadatjoo, Firozeh Nemati, Gholamhossein Shirvani, Mohammad Amin Ahmadi Faghih, Mohsen Javaheri
Thioflavanones are prevalent heterocyclic structural units in pharmaceutical and biologically active compound (Scheme1). In this paper, the synthesis of 2-phenylthiochroman-4-ones and 2-phenyl-4H-1-benzothiopyran-4-one labeled with carboxyl-14 is demonstrated.
June 20, 2017: Journal of Labelled Compounds & Radiopharmaceuticals
https://www.readbyqxmd.com/read/28629854/inhibition-of-organic-anion-transporter-oat-activity-by-cigarette-smoke-condensate
#5
Katia Sayyed, Marc Le Vee, Ziad Abdel-Razzak, Olivier Fardel
Cigarette smoke condensate (CSC) has previously been shown to impair activity and expression of hepatic drug transporters. In the present study, we provided evidence that CSC also hinders activity of organic anion transporters (OATs), notably expressed at the kidney level. CSC thus cis-inhibited OAT substrate uptake in OAT1- and OAT3-transfected HEK293 cells, in a concentration-dependent manner (IC50=72.1μg/mL for OAT1 inhibition and IC50=27.3μg/mL for OAT3 inhibition). By contrast, OAT4 as well as the renal organic cation transporter (OCT) 2 were less sensitive to the inhibitory effect of CSC (IC50=351...
June 16, 2017: Toxicology in Vitro: An International Journal Published in Association with BIBRA
https://www.readbyqxmd.com/read/28621402/microwave-assisted-synthesis-of-hybrid-heterocycles-as-potential-anticancer-agents
#6
Avula Srinivas, Malladi Sunitha, Kammachichu Raju, Banothu Ravinder, Siluveru Anusha, Thallapalli Rajasri, Pothuganti Swapna, Dupa Sushmitha, Deva Swaroopa, Gurala Nikitha, Chakunta Rao
In a one pot procedure, a series of novel hybrid heterocycles 6a-g and 7a-g were prepared by condensation of (3aS,4S,6S,6aS)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carbaldehyde 5 with mercapto acids and primary amines in the presence of ZnCl2 under both microwave irradiation and conventional heating conditions. Compound 5 was prepared from di-acetone D-mannose via a click reaction, primary acetonide deprotection and oxidative cleavage. Characterization of new compounds has been done by IR, NMR, MS and elemental analysis...
June 2017: Acta Chimica Slovenica
https://www.readbyqxmd.com/read/28617513/reaction-of-s-geranyl-2-thiouracil-modified-oligonucleotides-with-alkyl-amines-leads-to-the-n2-alkyl-isocytosine-derivatives
#7
Grazyna Leszczynska, Klaudia Sadowska, Malgorzata Sierant, Milena Sobczak, Barbara Nawrot, Elzbieta Sochacka
S-Geranylated 2-thiouridines (geS2Us) are unique hydrophobic modified nucleosides identified very recently in bacterial tRNAs. Our study on the synthesis of geS2Ura-containing oligonucleotides (geS2U-RNA and geS2dU-DNA) revealed a fast substitution of the S-geranyl moiety by methylamine (frequently used in oligonucleotide deprotection procedures) or n-butylamine, providing the corresponding N2-alkyl isocytosine (R2isoCyt) derivatives. To retain the S-geranyl moiety in the DNA or RNA chains, the optimized deprotection protocol with 8 M ethanolic ammonia should be applied...
June 15, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28612980/copper-catalyzed-oxidative-dehydrogenative-c-sp3-h-bond-amination-of-cyclo-alkanes-using-nh-free-heterocycles-as-amine-sources
#8
Chang-Sheng Wang, Xiao-Feng Wu, Pierre H Dixneuf, Jean-Francois Soule
A copper-catalyzed oxidative C(sp3)-H/N-H coupling of NH-heterocycles with affordable (cyclo)alkanes was developed. This protocol involved C(sp3)-N bond formation via a radical pathway generated by a homolytic cleavage of di-tert-butyl peroxide and trapping of the radical(s) by copper catalysts. The reaction tolerated a series of functional groups, such as bromo, fluoro, ester, ketone, nitrile, methyl and methoxy. NH-free indoles, pyroles, pyrazoles, indazoles and benzotriazoles have been successfully N-alkylated...
June 14, 2017: ChemSusChem
https://www.readbyqxmd.com/read/28605084/new-approach-to-1-4-benzoxazin-3-ones-by-electrochemical-c-h-amination
#9
Siegfried R Waldvogel, Lars Wesenberg, Sebastian Herold, Akihiro Shimizu, Jun-Ichi Yoshida
1,4-Benzoxazin-3-ones are important structural motifs in natural products and bioactive compounds. Usually the synthesis of benzoxazinones requires transition metal catalysts and pre-functionalized substrates, e.g. aryl halides. However, the anodic C,H amination of phenoxy acetates offers a very efficient and sustainable access to these heterocycles. The herein presented electrochemical protocol can be applied to a broad scope of alkylated substrates. Even tert-butyl moieties or halogen substituents are compatible with this versatile method...
June 12, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28598411/ruthenium-ii-catalysed-remote-c-h-alkylations-as-a-versatile-platform-to-meta-decorated-arenes
#10
Jie Li, Korkit Korvorapun, Suman De Sarkar, Torben Rogge, David J Burns, Svenja Warratz, Lutz Ackermann
The full control of positional selectivity is of prime importance in C-H activation technology. Chelation assistance served as the stimulus for the development of a plethora of ortho-selective arene functionalizations. In sharp contrast, meta-selective C-H functionalizations continue to be scarce, with all ruthenium-catalysed transformations currently requiring difficult to remove or modify nitrogen-containing heterocycles. Herein, we describe a unifying concept to access a wealth of meta-decorated arenes by a unique arene ligand effect in proximity-induced ruthenium(II) C-H activation catalysis...
June 9, 2017: Nature Communications
https://www.readbyqxmd.com/read/28597654/oms-2-supported-cu-hydroxide-catalyzed-benzoxazoles-synthesis-from-catechols-and-amines-via-domino-oxidation-process-at-room-temperature
#11
Xu Meng, Yanmin Wang, Yuanguang Wang, Baohua Chen, Zhenqiang Jing, Gexin Chen, Peiqing Zhao
In the presence of manganese oxide octahedral molecular sieve (OMS-2) supported copper hydroxide Cu(OH)x/OMS-2, aerobic synthesis of benzoxazoles from catechols and amines via domino oxidation/cyclization at room temperature is achieved. This heterogeneous benzoxazoles synthesis initiated by the efficient oxidation of catechols over Cu(OH)x/OMS-2 tolerates a variety of substrates, especially amines containing sensitive groups (hydroxyl, cyano, amino, vinyl, ethynyl, ester, and even acetyl groups) and heterocycles, which affords functionalized benzoxazoles in good to excellent yields by employing low catalyst loading (2 mol % Cu)...
June 14, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28581760/enantioselective-synthesis-of-functionalized-4-aryl-hydrocoumarins-and-4-aryl-hydroquinolin-2-ones-via-intramolecular-vinylogous-rauhut-currier-reaction-of-para-quinone-methides
#12
Xiang-Zhi Zhang, Kang-Ji Gan, Xiao-Xue Liu, Yu-Hua Deng, Fang-Xin Wang, Ke-Yin Yu, Jing Zhang, Chun-An Fan
A novel strategy for the asymmetric construction of functionalized 4-aryl-3,4-dihydrocoumarins and 4-aryl-3,4-dihydroquinolin-2-ones via an intramolecular vinylogous Rauhut-Currier reaction of para-quinone methides (p-QMs) under the bifunctional catalysis of chiral amine-phosphine is described. This intramolecular mode for the catalytic enantioselective 1,6-conjugate addition of p-QMs has been explored for the first time, delivering two types of synthetically important heterocycles in high yields and enantioselectivites...
June 5, 2017: Organic Letters
https://www.readbyqxmd.com/read/28578586/origin-of-somatic-mutations-in-%C3%AE-catenin-versus-adenomatous-polyposis-coli-in-colon-cancer-random-mutagenesis-in-animal-models-versus-nonrandom-mutagenesis-in-humans
#13
Da Yang, Min Zhang, Barry Gold
Wnt signaling is compromised early in the development of human colorectal cancer (CRC) due to truncating nonsense mutations in adenomatous polyposis coli (APC). CRC induced by chemical carcinogens, such as heterocyclic aromatic amines and azoxymethane, in mice also involves dysregulation of Wnt signaling but via activating missense mutations in the β-catenin oncogene despite the fact that genetically modified mice harboring an inactive APC allele efficiently develop CRC. In contrast, activating mutations in β-catenin are rarely observed in human CRC...
June 15, 2017: Chemical Research in Toxicology
https://www.readbyqxmd.com/read/28576974/lecithin-cholesterol-acyltransferase-activation-by-sulfhydryl-reactive-small-molecules-role-of-cysteine-31
#14
Lita A Freeman, Stephen J Demosky, Monika Konaklieva, Rostislav Kuskovsky, Angel Aponte, Alice F Ossoli, Scott M Gordon, Ross F Koby, Kelly A Manthei, Min Shen, Boris Vaisman, Robert D Shamburek, Ajit Jadhav, Laura Calabresi, Marjan Gucek, John J G Tesmer, Rodney L Levine, Alan T Remaley
BACKGROUND: Lecithin:cholesterol acyltransferase (LCAT) catalyzes plasma cholesteryl ester formation and is defective in Familial LCAT Deficiency (FLD), an autosomal recessive disorder characterized by low HDL, anemia and renal disease. OBJECTIVE: To investigate the mechanism by which Compound A, a small heterocyclic amine, activates LCAT. METHODS: Effect of Compound A on LCAT was tested in human plasma and with recombinant LCAT. Mass spectrometry and NMR was used to determine Compound A adduct formation with LCAT...
June 2, 2017: Journal of Pharmacology and Experimental Therapeutics
https://www.readbyqxmd.com/read/28558240/mitsunobu-reaction-using-basic-amines-as-pronucleophiles
#15
Hai Huang, Jun Yong Kang
A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system...
June 15, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28556614/preparation-of-arginine-modified-reduced-graphene-oxide-composite-filled-in-an-on-line-solid-phase-extraction-disk-and-its-application-in-the-analysis-of-heterocyclic-aromatic-amines
#16
Lemei Cai, Na Xu, Shujun Xia, Yiru Wang, Xi Chen
An arginine-modified reduced graphene oxide composite was prepared in an on-line solid phase extraction disk and coupled to high-performance liquid chromatography for the re-enrichment of heterocyclic aromatic amines. The synthetic composite presented an excellent adsorption capability because of the ultrahigh active surface area of graphene and the abundant alkaline groups of arginine. The adsorption capacity of it was 52.7 mg 2-amino-3-methyl-imidazo[4,5-f]-quinoline per gram, nearly twice that of threonine-modified reduced graphene oxide composite, glutamic acid modified reduced graphene oxide composite and reduced graphene oxide...
May 27, 2017: Journal of Separation Science
https://www.readbyqxmd.com/read/28545815/succinamide-derivatives-of-melampomagnolide-b-and-their-anti-cancer-activities
#17
Venumadhav Janganati, Jessica Ponder, Shraddha Thakkar, Craig T Jordan, Peter A Crooks
A series of succinamide derivatives of melampomagnolide B have been synthesized by coupling MMB monosuccinate (2) with various heterocyclic amines to afford compounds 3a-3l. MMB monosuccinate was also reacted with terminal diaminoalkanes to afford dimeric succinamido analogs of MMB (4a-4h). These succinamide analogs of MMB were evaluated for their anti-cancer activity against a panel of sixty human cancer cell lines. Analogs 3d-3i and dimers 4f-4g exhibited promising anti-cancer activity with GI50 values ranging from 0...
May 8, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28537596/unique-physicochemical-and-catalytic-properties-dictated-by-the-b3no2-ring-system
#18
Hidetoshi Noda, Makoto Furutachi, Yasuko Asada, Masakatsu Shibasaki, Naoya Kumagai
The expansion of molecular diversity beyond what nature can produce is a fundamental objective in chemical sciences. Despite the rich chemistry of boron-containing heterocycles, the 1,3-dioxa-5-aza-2,4,6-triborinane (DATB) ring system, which is characterized by a six-membered B3NO2 core, remains elusive. Here, we report the synthesis of m-terphenyl-templated DATB derivatives, displaying high stability and peculiar Lewis acidity arising from the three suitably arranged boron atoms. We identify a particular utility for DATB in the dehydrative amidation of carboxylic acids and amines, a reaction of high academic and industrial importance...
June 2017: Nature Chemistry
https://www.readbyqxmd.com/read/28536864/rabbit-n-acetyltransferase-2-genotyping-method-to-investigate-role-of-acetylation-polymorphism-on-n-and-o-acetylation-of-aromatic-and-heterocyclic-amine-carcinogens
#19
David W Hein, Mark A Doll
The rabbit was the initial animal model to investigate the acetylation polymorphism expressed in humans. Use of the rabbit model is compromised by lack of a rapid non-invasive method for determining acetylator phenotype. Slow acetylator phenotype in the rabbit results from deletion of the N-acetyltransferase 2 (NAT2) gene. A relatively quick and non-invasive method for identifying the gene deletion was developed and acetylator phenotypes confirmed by measurement of N- and O-acetyltransferase activities in hepatic cytosols...
May 23, 2017: Archives of Toxicology
https://www.readbyqxmd.com/read/28529787/crystal-structure-of-2-chloro-1-3-bis-2-6-diiso-propyl-phen-yl-1-3-2-di-aza-phospho-lidine-2-oxide
#20
Alex J Veinot, Arthur D Hendsbee, Jason D Masuda
The title compound, C26H38ClN2OP, was synthesized by reacting phosphoryl chloride with N,N'-bis-(2,6-diiso-propyl-phen-yl)ethane-1,2-di-amine in the presence of N-methyl-morpholine which acted as an auxilliary base to quench the HCl released as a by-product. The resultant N-heterocyclic phosphine five-membered ring adopts a half-chair conformation and features a tetra-coordinate P atom ligated by the chelating di-amine [P-N = 1.6348 (14) and 1.6192 (14) Å], one double-bonded O atom [P1-O1 = 1.4652 (12) Å] and one Cl atom [P1-Cl1 = 2...
May 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
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