title: Synthesis and anti-HIV activity of 3-alkylamido-3-deoxy-betulinic acid derivatives.
abstract: 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.
authors.affiliation: Niigata College of Pharmacy, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Kashiwada
authors.forename: J
authors.initials: J
authors.lastname: Chiyo
authors.forename: Y
authors.initials: Y
authors.lastname: Ikeshiro
authors.forename: T
authors.initials: T
authors.lastname: Nagao
authors.forename: H
authors.initials: H
authors.lastname: Okabe
authors.forename: L M
authors.initials: LM
authors.lastname: Cosentino
authors.forename: K
authors.initials: K
authors.lastname: Fowke
authors.forename: S L
authors.initials: SL
authors.lastname: Morris-Natschke
authors.forename: K H
authors.initials: KH
authors.lastname: Lee
mesh_terms: 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
chemical_list: D019380:Anti-HIV Agents; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; D000094062:Betulinic Acid