Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone.
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.
Stagliano
Kenneth W
KW
Department of Biological, Chemical and Physical Sciences, Illinois Institute of Technology, Chicago, 60616, USA.
Emadi
Ashkan
A
Lu
Zhenhai
Z
Malinakova
Helena C
HC
Twenter
Barry
B
Yu
Min
M
Holland
Louis E
LE
Rom
Amanda M
AM
Harwood
John S
JS
Amin
Ronak
R
Johnson
Allison A
AA
Pommier
Yves
Y
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
D019380:Anti-HIV Agents; D009285:Naphthoquinones; D011809:Quinones; C091977:conocurvone; D019427:HIV Integrase