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Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility

Rangaswamy, Javarappa and Kumar, Honnaiah Vijay and Harini, Salakatte Thammaiah and Naik, Nagaraja (2012) Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility. In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 22 (14). pp. 4773-4777.

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Official URL: http://dx.doi.org/10.1016/j.bmcl.2012.05.061

Abstract

In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively. (C) 2012 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to Elsevier
Keywords: Benzofuran based 1,3,5-substituted; pyrazole analogues; Substituted anilines; Antioxidant activity; Antimicrobial activity
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 13 Aug 2012 12:15
Last Modified: 13 Aug 2012 12:15
URI: http://eprints.iisc.ernet.in/id/eprint/44915

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