Substituted acrylophenones and related mannich bases as possible spermicides and inhibitors of HIV envelope glycoprotein-CD4 interaction.
Several appropriately substituted 4-(dialkylamino-alkyl)-substituted-styryl-alkyl ketones or acetophenones were prepared and subjected to the Mannich reaction to yield compounds that would incorporate both alpha,beta-unsaturated keto groups and a substituted aminomethyl function with or without another olefinic moiety at position 4. The spermicidal activity of the prepared compounds was evaluated. Several compounds 2d, 4a and 4e were found to possess spermicidal activity at 0.005% concentration, while compounds 2a, 2c, 2f, 3a and 4b were active at 0.01% concentration. Compounds 2a, 2c, 3a, 4a and 4e also inhibited the interaction between recombinant HIV Env and CD4. Out of these, compound 2c was found to be most active.
Kumaria
Niharika
N
Division of Pharmaceutics, Central Drug Research Institute, CDRI, Chatter Manzil, PO Box 173, 226 001, Lucknow, India.
Dwivedi
Anil Kumar
AK
Maikhuri
Jagdamba Prasad
JP
Gupta
Gopal
G
Habib
Saman
S
Dhar
Janak Dulari
JD
Singh
Satyawan
S
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D015704:CD4 Antigens / Q000378:metabolism; D002461:Cell Line, Transformed; D019302:HIV Envelope Protein gp160 / Q000187:drug effects* / Q000378:metabolism; D006801:Humans; D007659:Ketones / Q000138:chemical synthesis / Q000494:pharmacology; D008297:Male; D008352:Mannich Bases / Q000138:chemical synthesis / Q000494:pharmacology; D011485:Protein Binding / Q000187:drug effects; D013089:Spermatocidal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D013094:Spermatozoa / Q000187:drug effects; D013329:Structure-Activity Relationship
D019380:Anti-HIV Agents; D001555:Benzene Derivatives; D015704:CD4 Antigens; D019302:HIV Envelope Protein gp160; D007659:Ketones; D008352:Mannich Bases; D013089:Spermatocidal Agents