Showdomycin
Title: Showdomycin
CAS Registry Number: 16755-07-0
CAS Name: 3-b-D-Ribofuranosyl-1H-pyrrole-2,5-dione
Additional Names: 2-b-D-ribofuranosylmaleimide
Molecular Formula: C9H11NO6
Molecular Weight: 229.19
Percent Composition: C 47.16%, H 4.84%, N 6.11%, O 41.89%
Literature 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.
Properties: Leaflets from acetone + benzene, mp 153-154°. [a]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).
Melting point: mp 153-154°
Optical Rotation: [a]D22.5 +49.9° (H2O)
Absorption maximum: uv max: 220-221 nm (E1%1cm 422)
Toxicity data: LD50 in mice (mg/kg): 25 i.p.; 18 s.c.; 110 i.v. (Nishimura)

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