212. Albofungin

Nomenclature

CAS number: 37895-35-5
[1S-(1α,4α,8aα)]-13-Amino-3,4,8a,13-tetrahydro-1,15,16-trihydroxy-4-methoxy-12-methyl-1H-xantheno[4′,3′,2′:4,5][1,3]benzodioxino[7,6-g]isoquinoline-14,17(2H,9H)-dione.
C27H24N2O9; mol wt 520.49.
C 62.30%, H 4.65%, N 5.38%, O 27.67%.

Description and references

Antifungal antibiotic produced by Streptomyces albus var fungistaticus (fungatus) Solovyeva et Rudaya. Isoln procedure: Khokhlov, Liberman, Proc. Symp. Antibiotics Prague (May 1959) p 81. Structure: A. I. Gurevich et al., Tetrahedron Lett. 1972, 1751. Stereochemistry: A. I. Gurevich et al., ibid. 1974, 2801. Thought to be identical with Ba-180265 described by Liu et al., in Antimicrob. Agents Chemother. 1962, 767. Chemical and biological properties: A.I. Gurevich et al., Antibiotiki 17, 771 (1972).

Chemical structure

Properties

Crystals from nitromethane, mp 304-307°. Also reported as mp 190° (dec). [α]D20 670° (DMF). uv max (ethanol): 228, 254, 303, 376 nm (log ε 4.58, 4.58, 4.19, 4.42). Practically insol in water, petr ether. Sparingly sol in alcohol; quite sol in chloroform, dichloroethane, acetone, chlorobenzene, formamide, dimethylformamide, glacial acetic acid.