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A series of semisynthetic triterpenoids with A-ring azepano- and A-seco-fragments as well as hydrazido/hydrazono-substituents at C3 and C28 has been synthesized and evaluated for antimicrobial activity against key ESKAPE pathogens and DNA viruses (HSV-1, HCMV, HPV-11). It was found that azepanouvaol 8, 3-amino-3,4-seco-4(23)-en derivatives of uvaol 21 and glycyrrhetol-dien 22 as well as azepano-glycyrrhetol-tosylate 32 showed strong antimicrobial activities against MRSA with MIC ≤ 0.15 μM that exceeds the effect of antibiotic vancomycin. Azepanobetulinic acid cyclohexyl amide 4 exhibited significant bacteriostatic effect against MRSA (MIC ≤ 0.15 μM) with low cytotoxicity to HEK-293 even at a maximum tested concentration of &gt;20 μM (selectivity index SI 133) and may be considered a noncytotoxic anti-MRSA agent. Azepanobetulin 1, azepanouvaol 8, and azepano-glycyrrhetol 15 showed high potency towards HCMV (EC 50 0.15; 0.11; 0.11 µM) with selectivity indexes SI 50 115; 136; 172, respectively. The docking studies suggest the possible interactions of the leading compounds with the molecular targets.

Evaluation of A-azepano-triterpenoids and related derivatives as antimicrobial and antiviral agents