HPLC enantioseparation, absolute configuration determination and anti-HIV-1 activity of (±)-F18 enantiomers].

Racemic (±)-F18 (10-chloromethyl-11-demethyl-12-oxo-calanolide A), an analog of nature product (+)-calanolide A, is a new anti-HIV-1 nonnucleoside reverse transcript inhibitor (NNRTI). A successful enantioseparation of (±)-F18 offering (R)-F18 and (S)-F18 was achieved by a chiral stationary phase prepared HPLC. Their absolute configurations were determined by measurement of their electronic circular dichroisms combined with modem quantum-chemical calculations. Further investigation revealed that (R)-F18 and (S)-F18 shared a similar anti-HIV activities, however, (R)-F18 was more potent than (S)-F18 against wild-type virus, K101E mutation and P225H mutation pseudoviruses.

Citation

Lei-lei Zhang, Hai Xue, Li Li, Xiao-fan Lu, Zhi-wei Chen, Gang Lu. HPLC enantioseparation, absolute configuration determination and anti-HIV-1 activity of (±)-F18 enantiomers]. Yao xue xue bao = Acta pharmaceutica Sinica. 2015 Jun;50(6):733-7

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PMID: 26521445

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