Synthesis and anti-HIV study of novel acyclic guanine derivatives.
This paper reports a new method for synthesizing an acyclic version of 6 '-methylene and 6 '(alpha)-methylated carbovir analogues. The introduction of a methylene group to the requisite 6 '-position was carried out employing a Mannich type reaction using Eshenmoser's salt (methylene-N,N-dimethylammonium iodide). Carbonyl enolate alkylation (LiHMDS, CH3I) was used to introduce a methyl group to the 6 '(alpha)-position. The guanine analogues were successfully synthesized from the bromide compound 8 and 14 via a SN2 type reaction and deprotection. When the synthesized compounds 11 and 17 were tested against HIV-1, they showed toxicity that was not related to any anti-HIV activity.
Kim
Aihong
A
BK21-Project Team, College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
Hong
Joon Hee
JH
D019380:Anti-HIV Agents / Q000494:pharmacology; D045744:Cell Line, Tumor; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D006147:Guanine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D015658:HIV Infections / Q000188:drug therapy; D006801:Humans; D013601:T-Lymphocytes / Q000821:virology
D019380:Anti-HIV Agents; D015224:Dideoxynucleosides; C057503:carbovir; D006147:Guanine