Synthesis of novel benzofuran-gathered c-2,4,6-substituted pyrimidine derivatives conjugated by sulfonyl chlorides: orally bioavailable, selective, effective antioxidants and antimicrobials drug candidates

Rangaswamy, J. and Kumar, H. V. and Harini, S. T. and Naik, N. (2015) Synthesis of novel benzofuran-gathered c-2,4,6-substituted pyrimidine derivatives conjugated by sulfonyl chlorides: orally bioavailable, selective, effective antioxidants and antimicrobials drug candidates. JOURNAL OF HETEROCYCLIC CHEMISTRY, 52 (5). pp. 1349-1360. ISSN 1943-5193

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Official URL: http://doi.org/10.1002/jhet.2209

Abstract

In the present study, we have made an effort to develop the novel synthetic antioxidants and antimicrobials with improved potency. The novel benzofuran-gathered C-2,4,6-substituted pyrimidine derivatives 5a, 5b, 5c, 5d, 5e, 5f, 6a, 6b, 6c, 6d, 6e, 6f, 7a, 7b, 7c, 7d, 7e, 7f, 8a, 8b, 8c, 8d, 8e, 8f, 9a, 9b, 9c, 9d, 9e, 9f were synthesized by simple and efficient four-step reaction pathway. Initially, o-alkyl derivative of salicylaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, upon the treatment with potassium tertiary butoxide in the presence of molecular sieves. Further, Claisen-Schmidt condensation with aromatic aldehydes via treatment with thiourea followed by coupling reaction with different sulfonyl chlorides afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, H-1 NMR, C-13 NMR, mass, and elemental analysis and further screened for their antioxidant and antimicrobial activities. The results showed that the synthesized compounds 8b, 8e, 9b, and 9e produced significant antioxidant activity with 50% inhibitory concentration higher than that of reference, whereas compounds 7d and 7c produced dominant antimicrobial activity at concentrations 1.0 and 0.5mg/mL compared with standard Gentamicin and Nystatin, respectively.

Item Type: Article
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 31 May 2019 06:14
Last Modified: 31 May 2019 06:14
URI: http://eprints.uni-mysore.ac.in/id/eprint/736

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