title: Synthesis and evaluation of anti-HIV-1 and anti-HSV-1 activities of 4H-[1,2,4]-triazolo[1,5-a]pyrimidin-5-one derivatives.
abstract: In a one pot procedure, 18 compounds of 7-(substituted phenyl)-2-substituted-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a] pyrimidin-5-one derivatives (16-33) have been synthesized. 3(5)-Amino-5(3)-substituted-1,2,4-triazole derivatives (7-12) were used as synthomes which were cyclo-condensed by fusion with substituted methyl cinnamate esters (13-15) to afford the target compounds (16-33). In an effort to develop new non-nucleoside antiviral agents, compounds 16-33 were evaluated for their anti-HIV-1 and anti-HSV-1 activities. Complete inhibition of the proliferation of HIV-1 viruses was achieved by compounds 22, 23 and 24 at concentrations of 25, 25 and 50 micrograms/ml, respectively. 7-Phenyl-2-(n-pentyl)-6,7-dihydro-4H-[1,2,4]triazolo[1,5-a]pyrimidin-5-one (19) exhibited potential activity against HSV-1 with 88% reduction in the viral plaques. The suggested marked specificity of this class of compounds as anti-HIV-1 and HSV-1 agents is discussed.
authors.affiliation: Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Sugitani, Toyama, Japan. atef@acc.aun.eun.eg
authors.forename: Atef A
authors.initials: AA
authors.lastname: Abdel-Hafez
authors.forename: Hosny A H
authors.initials: HA
authors.lastname: Elsherief
authors.forename: Michiko
authors.initials: M
authors.lastname: Jo
authors.forename: Masahiko
authors.initials: M
authors.lastname: Kurokawa
authors.forename: Kimiyasu
authors.initials: K
authors.lastname: Shiraki
authors.forename: Takuya
authors.initials: T
authors.lastname: Kawahata
authors.forename: Toru
authors.initials: T
authors.lastname: Otake
authors.forename: Norio
authors.initials: N
authors.lastname: Nakamura
authors.forename: Masao
authors.initials: M
authors.lastname: Hattori
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002460:Cell Line; D003460:Crystallization; D015497:HIV-1 / Q000187:drug effects*; D018259:Herpesvirus 1, Human / Q000187:drug effects*; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D012997:Solvents; D013055:Spectrophotometry, Infrared; D010948:Viral Plaque Assay
chemical_list: D019380:Anti-HIV Agents; D000998:Antiviral Agents; D007202:Indicators and Reagents; D011743:Pyrimidines; D012997:Solvents