78151-96-9Relevant academic research and scientific papers
Un nouvel exemple de nucleoside a sucre ramifie insature: la desoxy-3'-methylidene-3'-adenosine
Tronchet, Jean M. J.,Tronchet, Jeannine F.
, p. 425 - 429 (1981)
Starting from 5-O-benzoyl-3-C-methylidene-3-deoxy-1,2-O-isopropylidene-α-D-erythro-pentofuranose (11) the title compound 8 has been prepared.Its α-anomer (9) and the acyclic sugar nucleoside 10 have been obtained as by-products.Adenosine deaminase slowly deaminated 8, 9 being not affected.Compound 8 exhibited no antiviral activity, whereas one of its saturated analogues (13) inhibited the multiplication of the herpes-1 (HF) virus.
Nucleic Acid Related Compounds. 70. Synthesis of 2'(and 3')-Deoxy-2'(and 3')-methyleneadenosines and Bis(methylene)furan 4',5'-Didehydro-5'-deoxy-2'(and 3')-methyleneadenosines. Inhibitors of S-Adenosyl-L-homocysteine Hydrolase and Ribonucleotide Reductase
Samano, Vicente,Robins, Morris J.
, p. 7108 - 7113 (2007/10/02)
Wittig treatment of 3',5'(or 2',5')-bis-O-silyl-2'(or 3')-ketoadenosine derivatives with methylenetriphenylphosphorane and deprotection gave the 2'(or 3')-deoxy-2'(or 3')-methyleneadenosines, respectively.Enzymatic deamination afforded the 2'(or 3')-deoxy-2'(or 3')-methyleneinosines.Treatment of 2'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-methylene-5'-O-tosyladenosine (14) with sodium 2-methyl-2-butoxide and deprotection gave 9-(3,5-dideoxy-3-methylene-β-D-glycero-pent-4-enofuranosyl)adenine (20).Analogous treatment of a protected 2',5'-dideoxy-5'-iodo-2'-methyleneadenosine derivative gave 9-(2,5-dideoxy-2-methylene-β-D-glycero-pent-4-enofuranosyl)adenine (22).Biochemical aspects of the putative mechanism-based inhibition of S-adenosyl-L-homocysteine hydrolase and ribonucleotide reductase by these compounds are discussed.
