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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

[ Vol. 16 , Issue. 1 ]

Author(s):

Issam A. Mohammed*, Mahmood Ahmed*, Rabia Ikram, Muhammad Muddassar, Muhammad Abdul Qadir and Khalijah Binti Awang   Pages 58 - 65 ( 8 )

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.

Keywords:

Flavan, antibacterial, mannich condensation, COX-2 enzyme, molecular docking.

Affiliation:

Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Institute of Chemistry, University of the Punjab, Lahore 54590, Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Department of Biosciences, COMSATS Institute of Information Technology, Park Road, Islamabad, Institute of Chemistry, University of the Punjab, Lahore 54590, Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603

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