title: 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.
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.
authors: 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.
authors: Hakan
authors: H
authors: Kandemir
authors: School of Environmental and Life Sciences, The University of Newcastle, Callaghan, NSW 2308, Australia.
authors: Cong
authors: C
authors: Ma
authors: School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
authors: Samuel K
authors: SK
authors: Kutty
authors: School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
authors: David Stc
authors: DS
authors: Black
authors: School of Medical Sciences, The University of New South Wales, Sydney, NSW 2052, Australia.
authors: Renate
authors: R
authors: Griffith
authors: School of Environmental and Life Sciences, The University of Newcastle, Callaghan, NSW 2308, Australia.
authors: Peter J
authors: PJ
authors: Lewis
authors: School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia. Electronic address: n.kumar@unsw.edu.au.
authors: Naresh
authors: N
authors: Kumar
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D012321:DNA-Directed RNA Polymerases; D007659:Ketones / Q000494:pharmacology*; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D007659:Ketones; D010069:Oxadiazoles; C583463:1,3,4-oxadiazole; D012321:DNA-Directed RNA Polymerases
keywords: Antimicrobial; Bis-indoles; Indole hydrazides; Oxadiazoles; RNA polymerase; Thiadiazoles