A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles

Subramanian Vedhanarayanan Karthikeyan; Subbu Perumal; Krithika Arun Shetty; Perumal Yogeeswari; Dharmarajan Sriram

doi:10.1016/j.bmcl.2009.04.029

A microwave-assisted facile regioselective Fischer indole synthesis and antitubercular evaluation of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles

Bioorg Med Chem Lett. 2009 Jun 1;19(11):3006-9. doi: 10.1016/j.bmcl.2009.04.029. Epub 2009 Apr 14.

Authors

Subramanian Vedhanarayanan Karthikeyan¹, Subbu Perumal, Krithika Arun Shetty, Perumal Yogeeswari, Dharmarajan Sriram

Affiliation

¹ Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, India.

PMID: 19403307
DOI: 10.1016/j.bmcl.2009.04.029

Abstract

A series of novel 2-aryl-3,4-dihydro-2H-thieno[3,2-b]indoles has been synthesised regioselectively in good yields from the reaction of 5-aryldihydro-3(2H)-thiophenones and arylhydrazine hydrochloride. This reaction is found to be assisted by microwaves. The thieno[3,2-b]indoles were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB). Among 22 compounds screened, [2-(2,4-dichlorophenyl)-7-fluoro-3,4-dihydro-2H-thieno[3,2-b]indole] (6t) was found to the most active compound with MIC of 0.4 microg/mL against MTB and MDR-TB.

Publication types

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

MeSH terms

Antitubercular Agents / chemical synthesis*
Antitubercular Agents / chemistry
Antitubercular Agents / pharmacology
Drug Resistance, Multiple, Bacterial / drug effects
Indoles / chemical synthesis*
Indoles / chemistry
Indoles / pharmacology
Microwaves
Mycobacterium tuberculosis / drug effects
Stereoisomerism
Structure-Activity Relationship

Substances

Antitubercular Agents
Indoles