Synthesis of 1,3-benzoxazines Based on 2,4,4-trimethyl-7,2’,4’-trihydroxy Flavan: Antibacterial, Anti-inflammatory, Cyclooxygenase-2 Inhibition and Molecular Modelling Studies

Mohammed, Issam Ahmed and Ahmed, Mahmood and Ikram, Rabia and Muddassar, Muhammad and Qadir, Muhammad Abdul and Awang, Khalijah (2018) Synthesis of 1,3-benzoxazines Based on 2,4,4-trimethyl-7,2’,4’-trihydroxy Flavan: Antibacterial, Anti-inflammatory, Cyclooxygenase-2 Inhibition and Molecular Modelling Studies. Letters in Drug Design & Discovery, 16 (1). pp. 58-65. ISSN 1570-1808

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Official URL: https://doi.org/10.2174/1570180815666180420100922

Abstract

Background: In the present study, the formation of 2, 4, 4-trimethyl-7,2’4’-trihydroxy flavan has been used as the key feature for the formation of new 1,3-benzoxazines. This reaction was carried out via Mannich-condensation reaction, the 7-hydroxy group of flavan was reacted with different primary amines in the presence of formaldehyde. Methods: All the synthesized compounds were characterized on the basis of FT-IR, NMR, MS and elemental analysis (CHN). Disk diffusion and 96-well plate assay methods were employed for the zone of inhibition and minimum inhibitory concentration determination, respectively to investigate the antibacterial activities. Results and Conclusion: Our studies showed that compound with electron withdrawing group on the benzene ring of 1,3-benzoxazines has promising antibacterial activities. An oral dose of 10 mg/kg body weight was administered to albino mice for acute toxicity of synthesized compounds. In vivo anti-inflammatory and in-vitro cyclooxygenase-2 (COX-2) studies showed that compound 11 was the most potent anti-inflammatory agent which inhibited induced edema by 62.7% while 68.7% inhibition of COX-2 was observed. The plausible binding mode of this compound in COX-2 enzyme was also determined using molecular docking simulations.

Item Type: Article
Uncontrolled Keywords: Antibacterial; COX-2 enzyme; Flavan; Mannich condensation; Molecular docking
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 15 May 2019 08:46
Last Modified: 15 May 2019 08:46
URI: http://eprints.um.edu.my/id/eprint/21246

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