Fredericamycin A
Structural Formula Vector Image
Title: Fredericamycin A
CAS Registry Number: 80455-68-1
CAS Name: (2S)-6¢,7¢-Dihydro-4,9,9¢-trihydroxy-6-methoxy-3¢-[(1E,3E)-1,3-pentadienyl]spiro[2H-benz[f]indene-2,8¢-[8H]cyclopent[g]isoquinoline]-1,1¢,3,5,8(2¢H)-pentone
Manufacturers' Codes: FCRC-A48; NSC-305263
Molecular Formula: C30H21NO9
Molecular Weight: 539.49
Percent Composition: C 66.79%, H 3.92%, N 2.60%, O 26.69%
Literature References: Antitumor antibiotic produced by Streptomyces griseus (FCRC-48); represents new structural class of antibiotics containing a spiro[4,4]nonane ring system. Isoln together with two biologically inactive components, fredericamycins B and C: R. C. Pandey et al., J. Antibiot. 34, 1389 (1981). Antimicrobial and cytotoxic activity in vitro and antitumor activity in vivo: D. J. Warnick-Pickle et al., ibid. 1402. Prepn and biological activity of water soluble salts: R. Misra, ibid. 51, 976 (1988). Structure determn by x-ray crystallography: R. Misra et al., J. Am. Chem. Soc. 104, 4478 (1982). Spectroscopic and mass spectral characterization: eidem, J. Antibiot. 40, 786 (1987). Synthetic studies: A. V. R. Rao et al., Chem. Commun. 1984, 1119; K. A. Parker et al., Tetrahedron Lett. 26, 2181 (1985). Synthesis of (±)-form: T. R. Kelly et al., J. Am. Chem. Soc. 108, 7100 (1986). Biosynthetic study: K. M. Byrne et al., Biochemistry 24, 478 (1985). Mechanism of action study: B. D. Hilton et al., ibid. 25, 5533 (1986).
Properties: Thin, platelet-like crystals from acetonitrile + water, mp >350° (dec). pKa (DMF) 6.80; 8.88. Sol in acetic acid, DMSO, DMF, pyridine; partially sol in acidic methanol, acidic chloroform, acidic ethyl acetate. Insol in water, petr ether, ether. Acts as an indicator: Red in acidic soln, green to blue in basic soln.
Melting point: mp >350° (dec)
pKa: pKa (DMF) 6.80; 8.88
Derivative Type: Potassium salt
Properties: Solubility (mg/ml): water (1.0); DMSO (8/1.5); 1:1 DMSO-H2O (3.0); also readily sol in DMF, dimethylacetamide, pyridine. Sparingly sol in ethyl acetate, acetonitrile, methanol, chloroform. Insol in hexanes, benzene, acetone, ether.

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