Nucleic acid related compounds. 47. Synthesis and biological activities of pyrimidine and purine "acyclic" nucleoside analogues.
Various acyclic, i.e., (2-hydroxyethoxy)methyl and (2-acetoxyethoxy)methyl, analogues of pyrimidine and purine nucleosides have been prepared and evaluated for their antiviral, antimetabolic, and cytotoxic properties. All of the pyrimidine analogues, including (E)-5-(2-bromovinyl)-1-[(2-hydroxyethoxy)methyl]uracil (12) and its O-acetyl derivative (13), were virtually devoid of antiviral, cytotoxic, and antimetabolic activities. However, several of the 8-substituted derivatives of 9-[(2-hydroxyethoxy)methyl]guanine (acyclovir) had higher antiviral specificity in vitro than the parent drug. The 8-methyl-, 8-amino-, 8-bromo-, and 8-iodoacyclovir derivatives have activities worthy of further investigation.
D000818:Animals; D000964:Antimetabolites, Antineoplastic / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002460:Cell Line; D007668:Kidney; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects; D013936:Thymidine / Q000378:metabolism; D014616:Vaccinia virus / Q000187:drug effects; D014721:Vesicular stomatitis Indiana virus / Q000187:drug effects
D000964:Antimetabolites, Antineoplastic; D000998:Antiviral Agents; D011684:Purine Nucleosides; D011741:Pyrimidine Nucleosides; D013936:Thymidine