4267. Fredericamycin A

Nomenclature

CAS number: 80455-68-1
(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; FCRC-A48; NSC-305263.
C30H21NO9; mol wt 539.49.
C 66.79%, H 3.92%, N 2.60%, O 26.69%.

Description and 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).

Chemical structure

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.

Derivative

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.