The synthesis of 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)quinolines by a SnCl(2)-catalyzed multicomponent reaction has been described. The reaction proceeds chemo- and regioselectively in an atom-economic way, generating a library of 24 quinoline derivatives.
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Identification, Synthesis, and Characterization of Potential Oxidative Impurities of Venetoclax: Application of Meisenheimer Rearrangement.
ACS Omega
October 2023
SVAK Lifesciences, ALEAP Industrial Area, Hyderabad 500090, Telangana, India.
Venetoclax is a potent BCL-2 inhibitor that is used for the treatment of several blood cancers. During the oxidative stress degradation of venetoclax, we observed the formation of two potential impurities at levels of about 8-10%, which have similar molecular weights. The two impurities were isolated and identified as 4-(3-((1-pyrrolo[2,3-]pyridin-5-yl)oxy)-4-(((3-nitro-4-(((tetrahydro-2-pyran-4-yl)methyl)amino)phenyl)sulfonyl)carbamoyl)phenyl)-1-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazine 1-oxide (venetoclax -oxide, ) and 2-((1-pyrrolo[2,3-]pyridin-5-yl)oxy)-4-(4-((4'-chloro-5,5-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methoxy)piperazin-1-yl)--((3-nitro-4-(((tetrahydro-2-pyran-4-yl)methyl)amino)phenyl)sulfonyl)benzamide (venetoclax hydroxylamine impurity, ).
View Article and Find Full Text PDFTopical VX-509 attenuates psoriatic inflammation through the STAT3/FABP5 pathway in keratinocytes.
Pharmacol Res
August 2022
The Department of Dermatology, Xiangya Hospital, Central South University, China; National Engineering Research Center of Personalized Diagnostic and Therapeutic Technology, China; Hunan Key Laboratory of Skin Cancer and Psoriasis, Xiangya Hospital, Central South University, China; Hunan Engineering Research Center of Skin Health and Disease, Xiangya Hospital, Central South University, China; National Clinical Research Center for Geriatric Disorders, Xiangya Hospital, Central South University, China. Electronic address:
Background: Psoriasis is a chronic inflammatory disease, with lesions mainly manifesting as scaly erythematous plaques. The mild or moderate of psoriasis is the main type of patients in hospital, and topical application remains the preferred treatment option for psoriasis therapy, therefore, the development of novel topical agents has an essential role in psoriasis therapy.
Objective: To identify potential drugs for psoriasis topical treatment.
Synthesis and preliminary evaluation of novel C-labeled GluN2B-selective NMDA receptor negative allosteric modulators.
Acta Pharmacol Sin
March 2021
Department of Radiology, Division of Nuclear Medicine and Molecular Imaging Massachusetts General Hospital and Harvard Medical School, 55 Fruit Street, Boston, MA, 02114, USA.
N-methyl-D-aspartate receptors (NMDARs) play critical roles in the physiological function of the mammalian central nervous system (CNS), including learning, memory, and synaptic plasticity, through modulating excitatory neurotransmission. Attributed to etiopathology of various CNS disorders and neurodegenerative diseases, GluN2B is one of the most well-studied subtypes in preclinical and clinical studies on NMDARs. Herein, we report the synthesis and preclinical evaluation of two C-labeled GluN2B-selective negative allosteric modulators (NAMs) containing N,N-dimethyl-2-(1H-pyrrolo[3,2-b]pyridin-1-yl)acetamides for positron emission tomography (PET) imaging.
View Article and Find Full Text PDFSynthesis and trypanocidal activity of a library of 4-substituted 2-(1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ols.
Eur J Med Chem
March 2017
Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil. Electronic address:
A library of 16 4-substituted 2-(1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ols 17-32 has been synthesized for use in biological testing against Trypanosoma cruzi, the protozoan parasite that causes Chagas disease. The 4-substituted 2-(1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ols 17-32 were subjected to biological testing to evaluate their efficacy against intracellular Trypanosoma cruzi (Y strain) amastigotes infecting U2OS human cells, with benznidazole as a reference compound. The assay was performed in duplicate (two independent experiments) and submitted to High Content Analysis (HCA) for determination of trypanocidal activity.
View Article and Find Full Text PDFMetabolism and Disposition of a Novel B-Cell Lymphoma-2 Inhibitor Venetoclax in Humans and Characterization of Its Unusual Metabolites.
Drug Metab Dispos
March 2017
Bioanalysis and Biotransformation, (H.L., M.J.M., K.W., J.S., M.S., J.S., S.M.M., A.J.L.), Process Chemistry (S.V.), and Clinical Pharmacology and Pharmacometrics (A.H.S., S.L.W., S.A., M.D.), Research & Development, AbbVie, North Chicago, Illinois; Clinical Pharmacy, Faculty of Pharmacy, Ain Shams University, Cairo, Egypt (A.H.S.); Eli Lilly and Company, Indianapolis, Indiana (Y.L.).
Article Synopsis
- - Venetoclax (ABT-199) is a B-cell lymphoma-2 (Bcl-2) inhibitor being developed for blood cancers, with studies showing that after a single oral dose in humans, the complete radioactive dose was recovered, mainly through feces, while very little was excreted in urine.
- - Around 65% of venetoclax is absorbed, with about 66% of the dose processed by the liver, resulting in several metabolites, including the unchanged drug and its nitro reduction metabolite M30, which was mostly found in feces.
- - One significant metabolite, M27, accounts for 12% of the drug-related material and is formed mainly through the cyto
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