2. Academic Validation
  3. Anti-AIDS agents 73: structure-activity relationship study and asymmetric synthesis of 3-O-monomethylsuccinyl-betulinic acid derivatives

Anti-AIDS agents 73: structure-activity relationship study and asymmetric synthesis of 3-O-monomethylsuccinyl-betulinic acid derivatives

  • Bioorg Med Chem Lett. 2007 Dec 1;17(23):6553-7. doi: 10.1016/j.bmcl.2007.09.081.
Keduo Qian 1,  Kyoko Nakagawa-Goto,  Donglei Yu,  Susan L Morris-Natschke,  Theodore J Nitz,  Nicole Kilgore,  Graham P Allaway,  Kuo-Hsiung Lee
Affiliations

Affiliation

  • 1 Natural Products Research Laboratories, School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599, USA.
PMID: 17935987 DOI: 10.1016/j.bmcl.2007.09.081
Abstract

3-O-3'(or 2')-Methylsuccinyl-betulinic acid (MSB) derivatives were separated by using recycle HPLC. The structures of four isomers were assigned by NMR and asymmetric synthesis. 3-O-3'S-Methylsuccinyl-betulinic acid (3'S-MSB, 4) exhibited potent anti-HIV activity with an EC(50) value of 0.0087microM and a TI value of 6.3x10(3), which is comparable to the data for bevirimat (DSB, PA-457), a current clinical trials drug that was also derived from betulinic acid. The anti-HIV potency of 4 was slightly better than that of AZT.

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