Inhibitors of Adenosine Deaminase: Synthesis of Coformycin and 3′-Deoxycoformycin

1983; Taylor & Francis; Volume: 2; Issue: 5 Linguagem: Inglês

10.1080/07328318308079413

ISSN

2332-3892

Autores

Lynn D. Hawkins, Jeffery C. Hanvey, F. Leslie Boyd, David C. Baker, H. D. Hollis Showalter,

Tópico(s)

Calcium signaling and nucleotide metabolism

Resumo

Abstract Glycosylation of the heterocycle, 6,7-dihydro-imidazo [4,5-d] [1,3] diazepin-8(3H)-one, with suitably protected sugars under the influence of Lewis acid catalysts gave the β-D-ribo- and 3′-deoxy-β-D-erythropento-furanosyl nucleosides. Deprotection and reduction of the keto nucleosides with sodium borohydride gave the (8R)- and (8S)-3-β-D-glycofuranosyl-3,6,7,8-tetrahydroimidazo [4,5-d]-[1,3] diazepin-8-ols, the (8R)-isomers of which are potent inhibitors of adenosine deaminase.

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