[The structure and antiviral activity of ribavirin analogs. II. Molecular and crystal structure of 1-(1,5-dihydroxy-3-oxapent-2-yl)-1,2,4-triazole-5-carboxamide].
X-ray structure of the title compound, an antiviral agent moderately active towards Herpes simplex virus type 1, has been determined. The space group is P2i/n, unit cell parameters: a = 10,119, b = 7,529, c = 13,585 A, beta = 107,82 degrees, Z = 4. The structure was solved by the direct method and refined by least-squares procedure to R = 2.9%. The gauche-conformation about C4'-C5' bond and trans-conformation about O4'-C4' bond are realized in the molecule. The carboxyamide group at the C5 atom of triazol cycle provides a steric opportunity for the intramolecular hydrogen bond C1'-H1'...O6 formation.
Tsapkina
E N
EN
Gurskaia
G V
GV
Zavgorodniĭ
S G
SG
Lindeman
S V
SV
Struchkov
Iu T
IuT
D000998:Antiviral Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D003460:Crystallization; D008958:Models, Molecular; D008968:Molecular Conformation; D012254:Ribavirin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D018139:Simplexvirus / Q000187:drug effects; D014230:Triazoles / Q000138:chemical synthesis* / Q000494:pharmacology
D000998:Antiviral Agents; D014230:Triazoles; C058359:1-(1,5-dihydroxy-3-oxapent-2-yl)-1,2,4-triazole-5-carboxamide; D012254:Ribavirin
Struktura i protivovirusnaia aktivnost' analogov ribavirina. II. Molekuliarnaia i kristallicheskaia struktura 1-(1,5-digidroksi-3-oksapent-2-il)-1,2,4-triazol-5-karboksamida.