Synthesis and anti-HIV activity of 3-alkylamido-3-deoxy-betulinic acid derivatives.
3-Alkylamido-3-deoxy-betulinic acids were synthesized and evaluated for anti-HIV activity as part of the structure-activity relationship study of the potent anti-HIV agent 3-O-(3',3'-dimethyl)-succinyl-betulinic acid (DSB) (2). 3Alpha-diglycorylamide-3-deoxy-betulinic acid demonstrated relatively potent anti-HIV activity (EC50 0.24 microm, TI 728). However, replacing the ester group at C-3 in 2 and its analogues with an amido group yielded inactive or much less potent compounds against HIV replication, indicating that the ester group at C-3 in 2-4 is essential for potent anti-HIV activity.
Kashiwada
Y
Y
Niigata College of Pharmacy, Japan.
Chiyo
J
J
Ikeshiro
Y
Y
Nagao
T
T
Okabe
H
H
Cosentino
L M
LM
Fowke
K
K
Morris-Natschke
S L
SL
Lee
K H
KH
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D015497:HIV-1 / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D053978:Pentacyclic Triterpenes; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014779:Virus Replication; D000094062:Betulinic Acid
D019380:Anti-HIV Agents; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; D000094062:Betulinic Acid