Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds: A new class of antimicrobials and antioxidants

Rangaswamy, Javarappa and Kumar, Honnaiah Vijay and Harini, Salakatte Thammaiah and Naik, Nagaraja (2017) Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds: A new class of antimicrobials and antioxidants. In: ARABIAN JOURNAL OF CHEMISTRY, 10 (2). S2685-S2696.

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Abstract

A new class of functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds (4a-q) was synthesized by a four step reaction in good yields. Initially, o-alkyl derivative of salicyaldehyde (1) readily furnished corresponding 2-acetyl benzofuran (2) on treatment with potassium tert-butoxide (t-BuOK) in the presence of molecular sieves. Further, Claisen-Schmidt condensation reaction with 4-methoxy benzaldehyde and hydrazine hydrate followed by coupling of benzoyl chlorides afforded target compounds (4a-q). Representative of the synthesized compounds was characterized by IR, H-1 NMR, C-13 NMR, mass, elemental analysis and evaluated for antimicrobial and antioxidant activities. The results gathered are allowed to conclude that, all newly synthesized analogues exhibit a certain degree of antimicrobial and antioxidant activities. Among the analogues, compounds (4h) and (4j) showed an excellent antimicrobial activity in the well plate method. Meanwhile, compounds (4e-f), (4l) and (4p) showed good antioxidant activity, whereas compound (4g) and (4q) displayed dominant antioxidant efficacy compared to standard butylated hydroxy anisole (BHA). (C) 2013 King Saud University. Production and hosting by Elsevier B.V.

Item Type:	Journal Article
Publication:	ARABIAN JOURNAL OF CHEMISTRY
Publisher:	10.1016/j.arabjc.2013.10.012
Additional Information:	Copy right for this article belongs to the ELSEVIER SCIENCE BV, PO BOX 211, 1000 AE AMSTERDAM, NETHERLANDS
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	20 Jan 2018 05:52
Last Modified:	20 Jan 2018 05:52
URI:	http://eprints.iisc.ac.in/id/eprint/58839

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