Title: Anthramycin
CAS Registry Number: 4803-27-4
CAS Name: [11R-[2(E),11a,11ab]]-3-(5,10,11,11a-Tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo[2,1-c][1,4]benzodiazepin-2-yl)-2-propenamide
Additional Names: 5,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo[2,1-c][1,4]benzodiazepin-2-acrylamide
Molecular Formula: C16H17N3O4
Molecular Weight: 315.32
Percent Composition: C 60.94%, H 5.43%, N 13.33%, O 20.30%
Literature References: Antitumor antibiotic produced by Streptomyces refuineus var thermotolerans, NRRL 3143: Leimgruber et al., J. Am. Chem. Soc. 87, 5791 (1965); Berger et al., US 3361742 (1968 to Hoffmann-La Roche). Also from Streptomyces spadicogriseus: N. Komatsu et al., J. Antibiot. 33, 54 (1980). Structure: Leimgruber et al., J. Am. Chem. Soc. 87, 5793 (1965). Synthesis: eidem, ibid. 90, 5641 (1968); Batcho, Leimgruber, US 3524849 (1970 to Hoffmann-La Roche). Activity studies: Horwitz, Grollman, Antimicrob. Agents Chemother. 1968, 21. Biosynthesis: L. H. Hurley et al., J. Am. Chem. Soc. 97, 4372 (1975). Review: Kohn in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 3-11.
Properties: Yellow prisms from acetone + water, dec 188-194°. uv max (acetonitrile): 235, 333 nm (e 18,200, 31,800). [a]D25 +930° (DMF).
Optical Rotation: [a]D25 +930° (DMF)
Absorption maximum: uv max (acetonitrile): 235, 333 nm (e 18,200, 31,800)
Derivative Type: Methyl ether hydrate
Molecular Formula: C17H19N3O4.H2O
Molecular Weight: 347.37
Percent Composition: C 58.78%, H 6.09%, N 12.10%, O 23.03%
Properties: Pale yellow needles from methanol + water, dec above 120°.
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