title: Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone.
abstract: Unsymmetrical biquinone and trimeric quinone derivatives were synthesized using halotriflate-biselectrophilic naphthoquinones through stepwise regioselective quinone substitution chemistry and evaluated for their ability to inhibit the cytopathogenic effects of HIV-1 using an MTT colorimetric assay. Compounds were also screened for their ability to inhibit the activity of HIV-1 integrase in vitro. Pyranylated trimeric quinones and biquinones exhibited both antiviral activity and integrase inhibitory activity. Conocurvone 1 and trimeric quinone 21 were the most potent HIV integrase inhibitors in the series. All of the biquinones showed HIV inhibitory activity. Simple methoxy substituted biquinones did not inhibit HIV-1 integrase.
authors.affiliation: Department of Biological, Chemical and Physical Sciences, Illinois Institute of Technology, Chicago, 60616, USA.
authors.forename: Kenneth W
authors.initials: KW
authors.lastname: Stagliano
authors.forename: Ashkan
authors.initials: A
authors.lastname: Emadi
authors.forename: Zhenhai
authors.initials: Z
authors.lastname: Lu
authors.forename: Helena C
authors.initials: HC
authors.lastname: Malinakova
authors.forename: Barry
authors.initials: B
authors.lastname: Twenter
authors.forename: Min
authors.initials: M
authors.lastname: Yu
authors.forename: Louis E
authors.initials: LE
authors.lastname: Holland
authors.forename: Amanda M
authors.initials: AM
authors.lastname: Rom
authors.forename: John S
authors.initials: JS
authors.lastname: Harwood
authors.forename: Ronak
authors.initials: R
authors.lastname: Amin
authors.forename: Allison A
authors.initials: AA
authors.lastname: Johnson
authors.forename: Yves
authors.initials: Y
authors.lastname: Pommier
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003124:Colorimetry; D019427:HIV Integrase / Q000378:metabolism*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D011809:Quinones / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D019380:Anti-HIV Agents; D009285:Naphthoquinones; D011809:Quinones; C091977:conocurvone; D019427:HIV Integrase