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.