Synthesis, molecular docking and anti-mycobacterial evaluation of new imidazo1,2-a]pyridine-2-carboxamide derivatives

New anti-tubercular agents, imidazo1,2-a]pyridine-2-carboxamide derivatives (5a-q) have been designed and synthesized. The structural considerations of the designed molecules were further supported by the docking study with a long-chain enoyl-acyl carrier protein reductase (InhA). The chemical structures of the new compounds were characterized by IR, H-1 NMR, C-13 NMR, HRMS and elemental analysis. In addition, single crystal X-ray diffraction has also been recorded for compound 5f. Compounds were evaluated in vitro against Mycobacterium tuberculosis H37Rv, and cytotoxicity against HEK-293T cell line. Amongst the tested compounds 5j, 5l and 5q were emerged as good anti-tubercular agents with low cytotoxicity. The structure-anti TB activity relationship of these derivatives was explained by molecular docking. (C) 2014 Elsevier Masson SAS. All rights reserved

Synthesis, molecular docking, antimycobacterial and antimicrobial evaluation of new pyrrolo3,2-c]pyridine Mannich bases

In this report, we describe the synthesis and biological evaluation of a new series of pyrrolo3,2-c]pyridine Mannich bases (7a-v). The Mannich bases were obtained in good yields by one-pot three component condensation of pyrrolo3,2-c]pyridine scaffold (6a-c) with secondary amines and excess of formaldehyde solution in AcOH. The chemical structures of the compounds were characterized by H-1 NMR, C-13 NMR, LC/MS and elemental analysis. Single crystal X-ray diffraction has been recorded for compound 7k (C23H29ClN4](+2), H2O). The in vitro antimicrobial activities of the compounds were evaluated against various bacterial and fungal strains using Agar diffusion method and Broth micro dilution method. Compounds 7e, 7f, 7r, 7t, and 7u were showed good Gram-positive antibacterial activity against S. aureus, B. flexus, C sporogenes and S. mutans. Furthermore, in vitro antimycobacterial activity was evaluated against Mycobacterium tuberculosis H37Rv (ATCC 27294) using MABA. Compounds 7r, 7t, and 7u were showed good antitubercular activity against Mtb (MIC >= 6.25 g/mL). Among the tested compounds, 14(4-chloro-2-(cyclohexylmethyl)-1H-pyrrolo3,2-clpyridin-3-yl)methyl) piperidine-3-carboxamide (7t) was showed excellent antimycobacterial activity against Mtb (MIC <0.78 mu g/mL) and low cytotoxicity against the HEK-293T cell line (SI 25). Molecular docking of the active compounds against glutamate racemase (Murl) and Mtb glutamine synthetase were explained the structure-activity observed in vitro. (C) 2017 Elsevier Masson SAS. All rights reserved

Synthesis, ABTS-Radical Scavenging Activity, and Antiproliferative and Molecular Docking Studies of Novel Pyrrolo[1,2-<i>a</i>]quinoline Derivatives

<div><p></p><p>A new 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS)-radical scavenging and antiproliferative agents of pyrrolo[1,2-<i>a</i>]quinoline derivatives have been synthesized. An efficient method for the synthesis of 14 novel diversified pyrrolo[1,2-<i>a</i>]quinoline derivatives has been described using 4-(1,3-dioxolan-2-yl)quinoline and different phenacyl bromides in acetone and followed by reacting with different acetylenes in dimethylformamide/K₂CO₃. The structure of the newly synthesized compounds was determined by infrared, ¹H NMR, ¹³C NMR, mass spectrometry, and elemental analysis. The in vitro antioxidant activity revealed that among all the tested compounds <b>5n</b> exhibited maximum scavenging activity with ABTS. Compound <b>5b</b> has showed good antiproliferative activity as an inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase.</p></div