Title: Stallimycin
CAS Registry Number: 636-47-5
CAS Name: N-[5-[[(3-Amino-3-iminopropyl)amino]carbonyl]-1-methyl-1H-pyrrol-3-yl]-4-[[[4-(formylamino)-1-methyl-1H-pyrrol-2-yl]carbonyl]amino]-1-methyl-1H-pyrrole-2-carboxamide
Additional Names: b-[1-methyl-4-[1-methyl-4-(1-methyl-4-formylaminopyrrole-2-carboxamido)pyrrole-2-carboxamido]pyrrole-2-carboxamido]propionamidine; distamycin A
Manufacturers' Codes: F.I. 6426
Molecular Formula: C22H27N9O4
Molecular Weight: 481.51
Percent Composition: C 54.88%, H 5.65%, N 26.18%, O 13.29%
Literature References: Antibiotic substance with antiviral and oncolytic properties, obtained from Streptomyces distallicus: Arcamone et al., DE 1039198 (1958 to Farmaceutici Italia), C.A. 55, 2012f (1961). Structure and synthesis: Arcamone et al., Nature 203, 1064 (1964); eidem, Gazz. Chim. Ital. 97, 1097, 1110 (1967). Total synthesis: M. Bialer et al., Tetrahedron 1978, 2389; L. Grehn, U. Ragnarsson, J. Org. Chem. 46, 3492 (1981). Toxicity and antitumor activity: A. DiMarco et al., Cancer Chemother. Rep. 18, 15 (1962). Review: Hahn in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 79-100.
Properties: mp 154-156°.
Melting point: mp 154-156°
Derivative Type: Hydrochloride
CAS Registry Number: 6576-51-8
Trademarks: Herperal (Farmitalia)
Molecular Formula: C22H27N9O4.HCl
Molecular Weight: 517.97
Percent Composition: C 51.01%, H 5.45%, N 24.34%, O 12.36%, Cl 6.84%
Properties: Crystals from dil HCl, mp 184-187° (Arcamone, 1967). Also reported as 189-193° from ethanol-ethyl acetate (Bialer). uv max (96% ethanol): 237, 303 nm (e 30000, 37000). LD50 in mice (mg/kg): 75 i.v.; 500 i.p. (DiMarco).
Melting point: mp 184-187° (Arcamone, 1967). Also reported as 189-193° from ethanol-ethyl acetate (Bialer)
Absorption maximum: uv max (96% ethanol): 237, 303 nm (e 30000, 37000)
Toxicity data: LD50 in mice (mg/kg): 75 i.v.; 500 i.p. (DiMarco)
Therap-Cat: Antiviral.
Keywords: Antiviral. |