8482. Showdomycin

Nomenclature

CAS number: 16755-07-0
3-β-d-Ribofuranosyl-1H-pyrrole-2,5-dione; 2-β-d-ribofuranosylmaleimide.
C9H11NO6; mol wt 229.19.
C 47.16%, H 4.84%, N 6.11%, O 41.89%.

Description and references

Nucleoside antibiotic isolated from Streptomyces showdoensis: Nishimura et al., J. Antibiot. 17A, 148 (1964); Nishimura, FR M2751 corresp to US 3316149 (1964, 1967, both to Shionogi). Structure: Nakagawa et al., Tetrahedron Lett. 1967, 4105; Darnall et al., Proc. Natl. Acad. Sci. USA 57, 548 (1967). Synthesis: Kalvoda et al., Tetrahedron Lett. 1970, 2297; Trummlitz, Moffatt, J. Org. Chem. 38, 1841 (1973); T. Sato et al., Tetrahedron Lett. 1978, 1829; J. G. Buchanan et al., J. Chem. Soc. Perkin Trans. 1 1979, 225; T. Inoue, I. Kuwajima, Chem. Commun. 1980, 251; A. P. Kozikowski, A. Ames, J. Am. Chem. Soc. 103, 3923 (1981); Y. Araki et al., Tetrahedron Lett. 29, 351 (1988). Exhibits antitumor activity: Shinzo et al., J. Antibiot. 17A, 234 (1964). Review: D. W. Visser, S. Roy-Burman in Antibiotics vol. 5(pt. 2), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 363-371.

Chemical structure

Properties

Leaflets from acetone + benzene, mp 153-154°. [α]D22.5 +49.9° (H2O). uv max: 220-221 nm (E1%1cm 422). Sol in water, alcohol, acetone, dioxane; insol in ethyl ether, benzene, petr ether. More stable in acid media than in neutral or alkaline. LD50 in mice (mg/kg): 25 i.p.; 18 s.c.; 110 i.v. (Nishimura).