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Design and synthesis of novel thiopheno-4-thiazolidinylindoles as potent antioxidant and antimicrobial agents

Jaiprakash S. Biradar, Parveen Rajesab, and B. Somappa Sasidhar

Central Research Lab, Department of Chemistry, Gulbarga University, Gulbarga, 585 106, Karnataka State, India

 

E-mail: jsbiradar@yahoo.com

Abstract: A novel and convenient synthesis of thiopheno-4-thiazolidinyl indole analogues is presented (IVa-IVi), with the aim of obtaining biologically active compounds. 3,5-disubstituted indol-2-carboxyhydrazides (Ia-If) were allowed to react with 3-acetyl-2,5-dichlorothiophene (II) to yield the corresponding 3,5-disubstituted indol-2-carbohydrazides (IIIa-IIIf). The pre-formed indolecarbohydrazides (IIIa-IIIf) were allowed to react with 2-mercaptoacetic acid or 2-mercaptopropanoic acid to produce thiopheno-4-thiazolidinylindoles (IVa-IVi). This reaction protocol affords a simple, eco-friendly, non-hazardous, easier preparation and high yields. The antioxidant (free radical scavenging, total antioxidant capacity and ferric-reducing antioxidant power) and antimicrobial activities of the synthesised compounds were evaluated. The structures and purity of the products were confirmed by their IR, 1H NMR, 13C NMR and mass spectral and analytical data. Most of the compounds tested showed very significant scavenging, antioxidant and antimicrobial activities. Compounds containing electron donor group (CH3) at the fifth position of indole exhibit an excellent ferric-reducing activity. The present study suggests that compounds IIIa-IIIb, IIIf, IVa-IVc, IVf-IVi, may serve as promising lead scaffolds for antioxidant and antimicrobial agents.

Keywords: indole carboxyhydrazide – indole carbohydrazide – thiopheno thiazolidinylindoles – dichlorothiophene – antioxidant activity – antimicrobial activity

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0452-3

 

Chemical Papers 68 (3) 392–400 (2014)

Thursday, June 20, 2024

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