Anti-AIDS agents. 31. Synthesis and anti-HIV activity of 4-substituted 3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (DCK) thiolactone analogs.
Four DCK-thiolactone analogs (3-6) were synthesized asymmetrically and evaluated for anti-HIV activity against HIV-1 replication in H9 lymphocyte cells. Based on the functionality on the thiolactonecoumarin nucleus, activity was in the order: methyl > H > propyl > benzyl. 4-Methyl-3',4'-di-O-(-)-camphanoyl-(+)-cis-khelthiolactone (4) exhibited extremely potent anti-HIV activity with EC50 and therapeutic index values of 0.00718 microM and > 21,300, respectively.
Yang
Z Y
ZY
Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill 27599, USA.
Xia
Y
Y
Xia
P
P
Cosentino
L M
LM
Lee
K H
KH
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D015497:HIV-1 / Q000187:drug effects / Q000502:physiology; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008214:Lymphocytes / Q000821:virology; D013329:Structure-Activity Relationship; D013871:Thiones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014779:Virus Replication / Q000187:drug effects
C116726:4-methyl-3',4'-di-O-camphanoylkhelthiolactone; D019380:Anti-HIV Agents; D007783:Lactones; D013871:Thiones