title: Design, synthesis and anti-mycobacterial activity of 1,2,3,5-tetrasubstituted pyrrolyl-N-acetic acid derivatives.
abstract: A novel synthesis of highly substituted pyrrole-N-acetic derivatives is described through the coupling of 1,4-diketones with amino acids following Paal-Knorr's approach. These pyrrole-N-acetic acid derivatives are found to exhibit potent anti-mycobacterial activity against Mycobacterium smegmatis and Mycobacterium tuberculosis strain H37Rv. In particular, 5n, 5q &5r are found to display excellent anti-mycobacterial activity against M. tuberculosis strain H37Rv with MIC values in the range of 2.97 μM. Conversely, these compounds showed low cytotoxicity (selectivity index: >16.83) against HEK-293T cell line.
authors.affiliation: Crop Protection Chemicals, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: Lakshmi Reddy
authors.initials: LR
authors.lastname: Pagadala
authors.affiliation: Department of Chemistry, Vikrama Simhapuri University, Nellore 524001, India.
authors.forename: Lakshmi Devi
authors.initials: LD
authors.lastname: Mukkara
authors.affiliation: Crop Protection Chemicals, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: Satyanarayana
authors.initials: S
authors.lastname: Singireddi
authors.affiliation: Chemical Biology, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: Ashita
authors.initials: A
authors.lastname: Singh
authors.affiliation: Department of Chemistry, Vikrama Simhapuri University, Nellore 524001, India.
authors.forename: Veera Reddy
authors.initials: VR
authors.lastname: Thummaluru
authors.affiliation: Department of Pharmacy, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, India.
authors.forename: Padma Sridevi
authors.initials: PS
authors.lastname: Jagarlamudi
authors.affiliation: Biology Division Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: Raja Sekhar
authors.initials: RS
authors.lastname: Guttala
authors.affiliation: Department of Pharmacy, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, India.
authors.forename: Yogeeswari
authors.initials: Y
authors.lastname: Perumal
authors.affiliation: Department of Pharmacy, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, India.
authors.forename: Sriram
authors.initials: S
authors.lastname: Dharmarajan
authors.affiliation: Biology Division Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: Suryanarayana Murty
authors.initials: SM
authors.lastname: Upadhyayula
authors.affiliation: Chemical Biology, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: Ramesh
authors.initials: R
authors.lastname: Ummanni
authors.affiliation: Natural Product Chemistry, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India.
authors.forename: Venkata Subba Reddy
authors.initials: VS
authors.lastname: Basireddy
authors.affiliation: Crop Protection Chemicals, Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, India. Electronic address: ravindra@iict.res.in.
authors.forename: Narender
authors.initials: N
authors.lastname: Ravirala
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000085:Acetates; D000900:Anti-Bacterial Agents; D011758:Pyrroles
keywords: Anti-mycobacterial activity; Paal–Knorr pyrrole synthesis; Stetter reaction