Synthesis and biological evaluation of 2,5-di(7-indolyl)-1,3,4-oxadiazoles, and 2- and 7-indolyl 2-(1,3,4-thiadiazolyl)ketones as antimicrobials

Hakan Kandemir, Cong Ma, Samuel K. Kutty, David Stc Black, Renate Griffith, Peter J. Lewis, Naresh Kumar

Research output: Journal article publicationJournal articleAcademic researchpeer-review

14 Citations (Scopus)

Abstract

A range of novel hydrazine bridged bis-indoles was prepared from readily available indole-7-glyoxyloylchlorides and 7-trichloroacetylindoles and underwent cyclodehydration to produce 2,5-di(7-indolyl)-1,3,4-oxadiazoles and a 2,2′-bi-1,3,4-oxadiazolyl with phosphoryl chloride in ethyl acetate. This efficient protocol was subsequently used for the synthesis of 2- and 7-indolyl 2-(1,3,4-thiadiazolyl)ketones from related indolyl-hydrazine carbothioamides. The synthesised bis-indoles were evaluated for their antimicrobial properties, particularly the inhibition of protein-protein complex formation between RNA polymerase and σ factor and their bactericidal effect on Gram positive Bacillus subtilis and Gram negative Escherichia coli.
Original languageEnglish
Pages (from-to)1672-1679
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume22
Issue number5
DOIs
Publication statusPublished - 1 Mar 2014
Externally publishedYes

Keywords

  • Antimicrobial
  • Bis-indoles
  • Indole hydrazides
  • Oxadiazoles
  • RNA polymerase
  • Thiadiazoles

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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