HPLC enantioseparation, absolute configuration determination and anti-HIV-1 activity of (±)-F18 enantiomers.
- Author:
Leilei ZHANG
;
Hai XUE
;
Li LI
;
Xiaofan LU
;
Zhiwei CHEN
;
Gang LU
- Publication Type:Journal Article
- From:
Acta Pharmaceutica Sinica
2015;50(6):733-7
- CountryChina
- Language:Chinese
-
Abstract:
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.
