Title: Porfiromycin
CAS Registry Number: 801-52-5
CAS Name: [1aS-(1aa,8b,8aa,8ba)]-6-Amino-8-[[(aminocarbonyl)oxy]methyl]-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethylazirino[2¢,3¢:3,4]pyrrolo[1,2-a]indole-4,7-dione
Additional Names: N-methylmitomycin C
Manufacturers' Codes: U-14743
Molecular Formula: C16H20N4O5
Molecular Weight: 348.35
Percent Composition: C 55.17%, H 5.79%, N 16.08%, O 22.96%
Literature References: Antibiotic substance isolated from a Streptomyces ardus fermentation broth: Herr et al., Antimicrob. Agents Annu. 1960, 23. Isoln from S. verticillatus and structure: Webb et al., J. Am. Chem. Soc. 84, 3185, 3187 (1962). Production process: Bohonos et al., US 3219530 (1965 to Am. Cyanamid). Synthesis of (±)-form: F. Nakatsubo et al., J. Am. Chem. Soc. 99, 8115 (1977). For stereochemistry and other synthetic studies, see Mitomycins.
Properties: Dark purple triclinic crystals, dec 201-201.5°. [a]D25 +275 ±55° (c = 0.1% in methanol); [a]D25 +242 ±100° (c = 0.045% in methanol). uv max (methanol): 217, 360, 555 nm (e 24600, 23000, 209). Slightly sol in water, moderately sol in polar organic solvents. Practically insol in hydrocarbon solvents.
Optical Rotation: [a]D25 +275 ±55° (c = 0.1% in methanol); [a]D25 +242 ±100° (c = 0.045% in methanol)
Absorption maximum: uv max (methanol): 217, 360, 555 nm (e 24600, 23000, 209)
Therap-Cat: Antibacterial; antineoplastic.
Keywords: Antineoplastic; Antibiotics and Analogs. |