title: Synthesis of novel L-N-MCd4T as a potent anti-HIV agent.
abstract: L-N-MCd4T (1) has been synthesized as a potent anti-HIV agent starting from (R)-epichlorohydrin using tandem alkylation, chemoselective reduction of ester in the presence of lactone functional group, RCM reaction and Mitsunobu reaction as key steps and was found to be a very potent anti-HIV-1 (EC50 = 6.76 microg mL(-1)) agent without cytotoxicity up to 100 microg mL(-1), indicating that the anti-HIV-1 activity found is similar to that of ddI (EC50 = 4.95 microg mL(-1)), which is used clinically for the treatment of AIDS patients.
authors.affiliation: Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University, Busan, Korea.
authors.forename: Ah-Young
authors.initials: AY
authors.lastname: Park
authors.forename: Hyung Ryong
authors.initials: HR
authors.lastname: Moon
authors.forename: Kyung Ran
authors.initials: KR
authors.lastname: Kim
authors.forename: Moon Woo
authors.initials: MW
authors.lastname: Chun
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006678:HIV / Q000187:drug effects; D006801:Humans; D008214:Lymphocytes / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: C476440:1-(5-(hydroxymethyl)bicyclo(3.1.0)hex-3-en-2-yl)-5-methyl-1,3-dihydropyrimidine-2,4-dione; D019380:Anti-HIV Agents; D001643:Bridged Bicyclo Compounds; D013936:Thymidine