685. Anthramycin
Nomenclature
CAS number: 4803-27-4
(2E)-3-[(11R,11aS)-5,10,11,11a-Tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo[2,1-c][1,4]benzodiazepin-2-yl]-2-propenamide; 5,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-5-oxo-1H-pyrrolo[2,1-c][1,4]benzodiazepin-2-acrylamide. C16H17N3O4; mol wt 315.32.
C 60.94%, H 5.43%, N 13.33%, O 20.30%.
Description and 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 (ε 18,200, 31,800). [α]D25 +930° (DMF).Derivative
Methyl ether hydrate.C17H19N3O4.H2O; mol wt 347.37.
C 58.78%, H 6.09%, N 12.10%, O 23.03%.