The assembly of beta-methylene-TAD, a metabolically stable analogue of the antitumor agent TAD, by the stepwise esterification of monodeprotected methylenebis-(phosphonate) benzyl esters under Mitsunobu conditions.
Synthesis of the metabolically stable analogue of thiazole-4-carboxamide adenine dinucleotide (beta-methylene-TAD) was achieved via the sequential monodeprotection of tetrabenzyl methylenebis(phosphonate) after two rounds of Mitsunobu esterifications with the corresponding nucleoside components, tiazofurin and adenosine.
Ikeda
H
H
Laboratory of Medicinal Chemistry, Division of Basic Sciences, National Cancer Institute, National Institutes of Health, Bethesda, MD 20892, USA.
Abushanab
E
E
Marquez
V E
VE
D000244:Adenosine Diphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D004951:Esterification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry; D010727:Phosphoric Diester Hydrolases / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis*
D000970:Antineoplastic Agents; D063065:Organophosphonates; D013844:Thiazoles; C085445:beta-methylene thiazole-4-carboxamide adenine dinucleotide; D000244:Adenosine Diphosphate; D010727:Phosphoric Diester Hydrolases; C050225:thiazole-4-carboxamide-adenine dinucleotide phosphodiesterase