ePrints@IIScePrints@IISc Home | About | Browse | Latest Additions | Advanced Search | Contact | Help

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

Jose, Gilish and Kumara, Tholappanavara H Suresha and Sowmya, B V Haliwana and Sriram, Dharmarajan and Row, Tayur N Guru and Hosamani, A Amar and More, S Sunil and Janardhan, Bhavya and Harish, B G and Telkar, Sandeep and Ravikumar, Yalegara Siddappa (2017) Synthesis, molecular docking, antimycobacterial and antimicrobial evaluation of new pyrrolo3,2-c]pyridine Mannich bases. In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 131 . pp. 275-288.

[img] PDF
Eur_Jou_Med_Che_131_275_2017.pdf - Published Version
Restricted to Registered users only

Download (2MB) | Request a copy
Official URL: https://doi.org/10.1016/j.ejmech.2017.03.015

Abstract

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.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER, 23 RUE LINOIS, 75724 PARIS, FRANCE
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Id for Latest eprints
Date Deposited: 20 May 2017 06:00
Last Modified: 20 May 2017 06:00
URI: http://eprints.iisc.ac.in/id/eprint/56933

Actions (login required)

View Item View Item