896. 8-Azaguanine

Nomenclature

CAS number: 134-58-7
5-Amino-1,4-dihydro-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one; 5-amino-1,6-dihydro-7H-v-triazolo[4,5-d]pyrimidine-7-one; 5-amino-1H-v-triazolo[d]pyrimidin-7-ol; 5-amino-7-hydroxy-1H-ν-triazolo[d]pyrimidine; pathocidin; guanazolo.
C4H4N6O; mol wt 152.11.
C 31.58%, H 2.65%, N 55.25%, O 10.52%.

Description and references

Triazolo analog of guanine. Prepd from 2,4,5-triamino-6-hydroxypyrimidine: Roblin, Jr. et al., J. Am. Chem. Soc. 67, 290 (1945); from 2-amino-5-nitro-4-oxopyrimidine: H. U. Blank et al., J. Org. Chem. 35, 1131 (1970). Formation from guanine by Streptomyces albus and identity with pathocidin: K. Hirasawa, K. Isono, J. Antibiot. 31A, 628 (1978). The first purine analog to show carcinostatic effects in murine malignancies; is readily incorporated into ribonucleic acids. Review: R. E. Parks, Jr., K. C. Agarwal, Handb. Exp. Pharmacol. 38, pt. 2, 458 (1975); D. Grunberger, G. Grunberger in Antibiotics vol. 5(pt. 2), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 110-123.

Chemical structure

Properties

Crystals from dil aq NaOH. Dec above 300° without melting. Absorption spectrum: L. F. Cavalieri et al., J. Am. Chem. Soc. 70, 3875 (1948). Soluble in dil caustic, in dil acids. Practically insol in water, alcohol, ether.

Use

Purine antimetabolite.