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

doi:10.1016/j.bmc.2014.01.025

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

Bioorg Med Chem. 2014 Mar 1;22(5):1672-9. doi: 10.1016/j.bmc.2014.01.025. Epub 2014 Jan 31.

Authors

Hakan Kandemir¹, Cong Ma², Samuel K Kutty³, David Stc Black³, Renate Griffith⁴, Peter J Lewis², Naresh Kumar⁵

Affiliations

¹ School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia; School of Chemistry, Faculty of Art and Science, Namık Kemal University, Turkey.
² School of Environmental and Life Sciences, The University of Newcastle, Callaghan, NSW 2308, Australia.
³ School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
⁴ School of Medical Sciences, The University of New South Wales, Sydney, NSW 2052, Australia.
⁵ School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia. Electronic address: n.kumar@unsw.edu.au.

PMID: 24525002
DOI: 10.1016/j.bmc.2014.01.025

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.

Keywords: Antimicrobial; Bis-indoles; Indole hydrazides; Oxadiazoles; RNA polymerase; Thiadiazoles.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / pharmacology*
DNA-Directed RNA Polymerases
Ketones / pharmacology*
Oxadiazoles / chemical synthesis*
Oxadiazoles / chemistry
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Ketones
Oxadiazoles
1,3,4-oxadiazole
DNA-Directed RNA Polymerases