title: [HPLC enantioseparation, absolute configuration determination and anti-HIV-1 activity of (±)-F18 enantiomers].
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.
authors.forename: Lei-lei
authors.initials: LL
authors.lastname: Zhang
authors.forename: Hai
authors.initials: H
authors.lastname: Xue
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.forename: Xiao-fan
authors.initials: XF
authors.lastname: Lu
authors.forename: Zhi-wei
authors.initials: ZW
authors.lastname: Chen
authors.forename: Gang
authors.initials: G
authors.lastname: Lu
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D015497:HIV-1 / Q000187:drug effects*; D039681:Pyranocoumarins / Q000737:chemistry*
chemical_list: C547679:10-chloromethyl-11-demethyl-12-oxocalanolide A; D019380:Anti-HIV Agents; D039681:Pyranocoumarins; C075959:calanolide A