Adenosine deaminase resistant antiviral purine nucleosides and m

Details Adenosine deaminase resistant antiviral purine nucleosides and m Adenosine deaminase resistant antiviral purine nucleosides and m

1979-01-05

1981-05-19

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen bonded directly to ring carbon of the purine ring...

C07D47334

Patent

active

042686725

ABSTRACT:
The preparation of (.+-.)-9-[.alpha.-(2.alpha.,3.beta.-dihydroxy-4.alpha.-(hydroxymethyl)cycl opentyl)]-6-substituted purines: ##STR1## and (.+-.)-3-[.alpha.-(2.alpha.,3.beta.-dihydroxy-4.alpha.-(hydroxymethyl)cycl opentyl)]-7-substituted-v-triazolo[4,5d]pyrimidines: ##STR2## and their derivatives wherein R is amino, mercapto, methylmercapto, hydroxy, halogen, or substituted amino: ##STR3## wherein R' and R" may be the same or different and are of hydrogen, methyl, ethyl, propyl or phenyl. The preparation of the single intermediate from which either of these series of compounds may be synthesized is also disclosed. The compounds exhibit antiviral and antitumor activity. Acid salts and esters of the purine nucleosides have also been prepared.

REFERENCES:
L. Bennett et al., Mol. Pharmacol. 4, 208-217 (1968), Metabolic Studies with Carbocyclic Analogs of Purine Nucleosides.
D. Hill et al., Chem. Abstracts, 75:86554s (1971), Inhibition of Guanine Metabolism of Mammalian Tumor Cells by the Carbocyclic Analog of Adenosine.
Y. Shealy et al., 4 Amer. Chem. Soc., (1969), 91, (11), 3075-3083, Synthesis of Carbocyclic Analogs of Purine Ribonucleosides.
A. Holy, Nucleic Acids Research, Spec. Publ., 1975, 1 (Symp. Chem. Nucleic Acids Components, 3rd, 1975), 573-576.

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