1877. Carzinophilin A

Nomenclature

CAS number: 106486-76-4
3-Methoxy-5-methyl-1-naphthalenecarboxylic acid (1S)-2-[[(1E)-1-[(3R,4R,5S)-3-(acetyloxy)-4-hydroxy-1-azabicyclo[3.1.0]hex-2-ylidene]-2-[[(1Z)-1-(hydroxymethylene)-2-oxopropyl]amino]-2-oxoethyl]amino]-1-[(2S)-2-methyloxiranyl]-2-oxoethyl ester; cardinophyllin; CZ; azinomycin B.
C31H33N3O11; mol wt 623.61.
C 59.71%, H 5.33%, N 6.74%, O 28.22%.

Description and references

Antitumor antibiotic; alkylates DNA by interstrand crosslinking of the major groove. Isoln from Streptomyces sahachiroi: T. Hata et al., J. Antibiot. 7A, 107 (1954). Purification: H. Kamada et al., ibid. 8A, 187 (1955). Mechanism of action: J. W. Lown, K. C. Majumdar, Can. J. Biochem. 55, 630 (1977); T. Fujiwara, I. Saito, Tetrahedron Lett. 40, 315 (1999). Proposed structure: J. W. Lown, C. C. Hanstock, J. Am. Chem. Soc. 104, 3213 (1982). Identity with azinomycin B: E. J. Moran, R. W. Armstrong, Tetrahedron Lett. 32, 3807 (1991). Purification: K. Nagaoka et al., J. Antibiot. 39, 1527 (1986). Total structure as azinomycin B: K. Yokoi et al., Chem. Pharm. Bull. 34, 4554 (1986).

Chemical structure

Properties

Amorphous white solid, mp 190° (dec). [α]D20 +48° (c = 0.48 in CHCl3). uv max (methanol): 217, 250, 340 nm (ε 65500, 30400, 8500). Sol in acetone, chloroform, ethyl acetate, methanol. Insol in diethyl ether, n-hexane, water.