Synthesis of [(2'S, 3'S)-bis(hydroxylmethyl)pyrrolidin-1-yl] purine and pyrimidine nucleosides as potential antiviral agents.
The enantiomerically pure synthesis of [(2'S, 3'S)-bis(hydroxymethyl)pyrrolidin-1-yl] thymine 17 and -adenine 20 was achieved via construction of the base on the 1-amino-pyrrolidine 15, and their anti-HSV-1 and -2, and anti-HIV-1 activities were evaluated.
Oohashi
T
T
Department of Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Nishiyama
S
S
Yamamura
S
S
Kato
K
K
D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D015497:HIV-1 / Q000187:drug effects*; D018259:Herpesvirus 1, Human / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013941:Thymine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
D000998:Antiviral Agents; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides; D011759:Pyrrolidines; D000225:Adenine; D013941:Thymine