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Bioorg Chem. 2017 Dec;75:181-200. doi: 10.1016/j.bioorg.2017.09.008. Epub 2017 Sep 12.

Chemical synthesis and in silico molecular modeling of novel pyrrolyl benzohydrazide derivatives: Their biological evaluation against enoyl ACP reductase (InhA) and Mycobacterium tuberculosis.

Author information

1
Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, Soniya Education Trust's, College of Pharmacy, Sangolli Rayanna Nagar, Dharwad 580 002, India. Electronic address: shrinivasdj@rediffmail.com.
2
Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, Soniya Education Trust's, College of Pharmacy, Sangolli Rayanna Nagar, Dharwad 580 002, India; Shree Dhanvantary Pharmacy College, Kim, Surat, India.
3
Novel Drug Design and Discovery Laboratory, Department of Pharmaceutical Chemistry, Soniya Education Trust's, College of Pharmacy, Sangolli Rayanna Nagar, Dharwad 580 002, India.
4
Universite de Toulouse, UPS, Laboratoire de Synthese et Physico-chimie de Molecules d'Interet Biologique, LSPCMIB, 118 Roote de Narbonne, F-31062 Toulouse Cedex 9, France; ITAV-USR3505, Université de Toulouse, CNRS, UPS, F-31106 Toulouse, France.

Abstract

In efforts to develop new antitubercular agents, we report here the synthesis of a series of novel pyrrole hydrazine derivatives. The molecules were evaluated against inhibitors of InhA, which is one of the key enzymes involved in type II fatty acid biosynthetic pathway of the mycobacterial cell wall as well as inhibitors of Mycobacterium tuberculosis H37Rv. The binding mode of compounds at the active site of enoyl-ACP reductase was explored using the surflex-docking method. The model suggests one or two H-bonding interactions between the compounds and the InhA enzyme. Some compounds exhibited good activities against InhA in addition to promising activities against M. tuberculosis.

KEYWORDS:

Antitubercular activity; Enoyl-ACP reductase; Molecular modeling; Pyrroles

PMID:
28961440
DOI:
10.1016/j.bioorg.2017.09.008
[Indexed for MEDLINE]

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