880. Aureothricin

Nomenclature

CAS number: 574-95-8
N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propanamide; 4-methyl-6-propionamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one; 5-methyl-3-propionamidopyrrolin-4-one[4,3-d]-1,2-dithiole; propionopyrrothine.
C9H10N2O2S2; mol wt 242.32.
C 44.61%, H 4.16%, N 11.56%, O 13.21%, S 26.47%.

Description and references

Antibiotic substance produced by Streptomyces sp 26A (Mitaka, Tokyo, June 1947) which resembles Nocardia farcinicus or Streptomyces lipmanii: Umezawa et al., Jpn. Med. J. 1, 512 (1948); Umezawa et al., J. Antibiot. 2, Suppl. A, 105 (1949); Maeda, ibid. 2, 793 (1949); Maeda, Jpn. Med. J. 2, 85 (1949); Celmer et al., J. Am. Chem. Soc. 74, 6304 (1952). Structure: Celmer, Solomons, ibid. 77, 2861 (1955). Prepn: Celmer, US 2752359 (1956 to Pfizer). Total synthesis: Schmidt, Geiger, Angew. Chem. 74, 328 (1962).

Chemical structure

Properties

Crystals, usually solvated. Stable in air. When anhydr dec 260-270° (sublimes near 200°). uv max: 248, 312, 388 nm (ε 6100, 3900, 11000). Practically insol in water; slightly sol in ethyl acetate, butyl acetate, acetone, benzene, ether, alc.