Synthesis and anti-HIV activity of 3-alkylamido-3-deoxy-betulinic acid derivatives

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Abstract

3-Alkylamido-3-deoxy-betulinic acids were synthesized and evaluated for anti-HIV activity as part of the structure-activity relationship study of the potent anti-HIV agent 3-O-(3',3'-dimethyl)-succinyl-betulinic acid (DSB) (2). 3α-Diglycorylamide-3-deoxy-betulinic acid demonstrated relatively potent anti-HIV activity (EC50 0.24 μM, TI 728). However, replacing the ester group at C-3 in 2 and its analogues with an amido group yielded inactive or much less potent compounds against HIV replication, indicating that the ester group at C-3 in 2-4 is essential for potent anti-HIV activity.

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Kashiwada, Y., Chiyo, J., Ikeshiro, Y., Nagao, T., Okabe, H., Cosentino, L. M., … Lee, K. H. (2000). Synthesis and anti-HIV activity of 3-alkylamido-3-deoxy-betulinic acid derivatives. Chemical and Pharmaceutical Bulletin, 48(9), 1387–1390. https://doi.org/10.1248/cpb.48.1387

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