15888-38-7Relevant articles and documents
Deamination of 5′-substituted-2′,3′-isopropylidene adenosine derivatives catalyzed by adenosine deaminase (ADA, EC 3.5.4.4) and complementary enzymatic biotransformations catalyzed by adenylate deaminase (AMPDA, EC 3.5.4.6): A viable route for the preparation of 5′-substituted inosine derivatives
Ciuffreda, Pierangela,Loseto, Angela,Santaniello, Enzo
, p. 5767 - 5771 (2002)
Adenosine deaminase (ADA) catalyzes the deamination of 2′,3′-isopropylidene adenosine and the corresponding 5′-amino derivative in a 3% dimethylsulfoxide aqueous solution. Whereas ADA is unable to convert other 5′-substituted derivatives (acetate, acetamido, azide), the enzyme adenylate deaminase (AMPDA) accepts all the above compounds as substrates for their biotransformation to the corresponding 5′-substituted inosine derivatives.
Identification of 8-aminoadenosine derivatives as a new class of human concentrative nucleoside transporter 2 inhibitors
Tatani, Kazuya,Hiratochi, Masahiro,Nonaka, Yoshinori,Isaji, Masayuki,Shuto, Satoshi
supporting information, p. 244 - 248 (2015/03/30)
Purine-rich foods have long been suspected as a major cause of hyperuricemia. We hypothesized that inhibition of human concentrative nucleoside transporter 2 (hCNT2) would suppress increases in serum urate levels derived from dietary purines. To test this hypothesis, the development of potent hCNT2 inhibitors was required. By modifying adenosine, an hCNT2 substrate, we successfully identified 8-aminoadenosine derivatives as a new class of hCNT2 inhibitors. Compound 12 moderately inhibited hCNT2 (IC50 = 52 ± 3.8 μM), and subsequent structure-activity relationship studies led to the discovery of compound 48 (IC50 = 0.64 ± 0.19 μM). Here we describe significant findings about structural requirements of 8-aminoadenosine derivatives for exhibiting potent hCNT2 inhibitory activity.
Acyl migration from N6 to N7 of a 2',3'-O-isopropylideneadenosine derivative accompained by cyclonucleoside formation
Anzai, Kentaro,Uzawa, Jun
, p. 2109 - 2114 (2007/10/02)
Reaction of 2',3'-O-isopropylideneadenosine (1) with p-NCC6H4COCl in 1:6 Et3N-CH2Cl2 afforded the cyanoimidazole nucleoside 8 (53percent) and the 8,5'-O-cycloadenosine derivative 7 (29percent).Treatment of N6,N6-di-p-toluyl-2',3'-O-isopropilideneadenosine (23) with ZnBr2 in p-dioxane resulted in acyl migration from N6 to N7 to give the cycloadenosine derivative 4.The coordination site of the zinc cation on the base moiety of adenosine derivatives was determined by 15N nmr spectra.
