title: Synthesis of (Z)- and (E)-9-[(2-hydroxyethylidene)cyclopropyl]adenine--new methylenecyclopropane analogues of adenosine and their substrate activity for adenosine deaminase.
abstract: Synthesis of Z- and E-methylenecyclopropane analogues of adenosine 3 and 4 by alkylation of adenine with novel alkylating agent 5 is described. The E-isomer 4 is a substrate for adenosine deaminase. Compounds 3 and 4 were tested for antiviral activity against HCMV, HSV-1, HSV-2, EBV, VZV, HBV and HIV-1.
authors.affiliation: Department of Chemistry, Barbara Ann Karmanos Cancer Institute, Wayne State University School of Medicine, Detroit, MI 48201-1379, USA.
authors.forename: Y L
authors.initials: YL
authors.lastname: Qui
authors.forename: M B
authors.initials: MB
authors.lastname: Ksebati
authors.forename: J
authors.initials: J
authors.lastname: Zemlicka
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D000243:Adenosine Deaminase / Q000737:chemistry* / Q000378:metabolism; D000478:Alkylation; D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002460:Cell Line; D003521:Cyclopropanes / Q000737:chemistry; D003587:Cytomegalovirus / Q000187:drug effects; D015497:HIV-1 / Q000187:drug effects; D006515:Hepatitis B virus / Q000187:drug effects; D014645:Herpesvirus 3, Human / Q000187:drug effects; D004854:Herpesvirus 4, Human / Q000187:drug effects; D006801:Humans; D018139:Simplexvirus / Q000187:drug effects; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C411042:1,2-dibromo-1-(2-methoxymethoxyethyl)cyclopropane; C411043:9-(2-hydroxyethylidene)-cyclopropyl adenine; D000998:Antiviral Agents; D003521:Cyclopropanes; D000243:Adenosine Deaminase; D000225:Adenine; D000241:Adenosine