Tricyclic etheno analogs of PMEG and PMEDAP: synthesis and biological activity.
A series of novel 9-substituted (2-(3H-imidazo[1,2-a]purin-3-yl)ethoxy)methylphosphonic and 4-substituted (2-(1H-imidazo[2,1-b]purin-1-yl)ethoxy)methylphosphonic acids as tricyclic etheno analogs of potent antivirals and cytostatics PMEG and PMEDAP was synthesized and evaluated for their biological activity. Most of the compounds showed modest activity against varicella-zoster virus (VZV) and human cytomegalovirus (HCMV) except for (2-(9-oxo-5,9-dihydro-3H-imidazo[1,2-a]purin-3-yl)ethoxy)methylphosphonic acid 8 which proved markedly active against VZV and HCMV. None of the compounds tested exhibited any significant cytostatic effect.
Horejsí
Katerina
K
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, CZ-166 10 Praha 6, Czech Republic.
Andrei
Graciela
G
De Clercq
Erik
E
Snoeck
Robert
R
Pohl
Radek
R
Holý
Antonín
A
D000225:Adenine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D003587:Cytomegalovirus / Q000187:drug effects; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014645:Herpesvirus 3, Human / Q000187:drug effects; D006801:Humans; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D009943:Organophosphorus Compounds; C063380:9-((2-phosphonylmethoxy)ethyl)guanine; C059499:9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine; D006147:Guanine; D000225:Adenine