title: [X-ray structural study of 3'-O-methylthiomethylthymidine and 3'-O-methylsulfinylmethylthymidine--potential inhibitors of HIV].
abstract: The molecular and crystalline structures of deoxiribonucleoside analogs: 3'-O-methylthiomethylthymidine monohydrate dT(CH2SMe).H2O and 3'-O-methylsulphinylmethylthymidine dT(CH2SOMe) were determined. The space group of dT(CH2SMe).H2O crystals is P2(1), the parameters of the elementary cell are a = 10.417(1), b = 4.912(2), c = 15.969(2) A, beta = 107.23(1) degrees, V = 780.5 A3, Z = 2, R = 3.8%. The crystals of dT(CH2SOMe have a space group P2(1)2(1)2(1), the elementary cell parameters are a = 8.858(2), b = 9.303(1), c = 17.698(2) A, V = 1458.3 A3, Z = 4, R = 2.8%. The dT(CH2SMe) and dT(CH2SOMe) molecules are characterized by an anti-conformation relative to the glycoside bond (angles chi (O4'-C1'-N1-C2) are equal to -116.2 degrees and -148.8 degrees), a gauche(+)-conformation relative to the exocyclic bond C4'-C5' (angles phi CO (C3'-C4'-C5'-O5') are equal to 52.1 degrees and 41.1 degrees). The conformation of the furanose cycle in the dT(CH2SMe) molecule is described by C2'-endo-C3'-exo (P = 167.8 degrees, psi m = 34.8 degrees) and in the dT(CH2SOMe) molecule by C2'-endo-C1'-exo (P = 148.4 degrees, psi m = 35.4 degrees). The structures studied were compared with 3'-azido-3'-deoxythymidine (AZT) and thymidine.
authors.forename: A V
authors.initials: AV
authors.lastname: Bochkarev
authors.forename: S G
authors.initials: SG
authors.lastname: Zavgorodniĭ
authors.forename: A S
authors.initials: AS
authors.lastname: Zhdanov
authors.forename: G V
authors.initials: GV
authors.lastname: Gurskaia
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry* / Q000494:pharmacology; D006678:HIV / Q000187:drug effects*; D009690:Nucleic Acid Conformation; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D014961:X-Ray Diffraction
chemical_list: C093780:3'-O-methylsulfinylmethylthymidine; C093781:3'-O-methylthiomethylthymidine; D000998:Antiviral Agents; D013936:Thymidine
vernacular_title: Rentgenostrukturnoe issledovanie 3'-O-metiltiometiltimidina i 3'-O-metilsul'finilmetiltimidina--potentsial'nykh ingibitorov VICh.