9342. Thiolutin

Nomenclature

CAS number: 87-11-6
6-(Acetamido)-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one; N-(4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)acetamide; 3-acetamido-5-methylpyrrolin-4-one[4,3-d]-1,2-dithiole; acetopyrrothine.
C8H8N2O2S2; mol wt 228.29.
C 42.09%, H 3.53%, N 12.27%, O 14.02%, S 28.09%.

Description and references

Antibiotic isolated from several strains of Streptomyces albus: F. W. Tanner, Jr. et al., 118th Am. Chem. Soc. Meet. (Chicago, Sept. 1950), Abstracts of Papers, p 18A; F. W. Tanner, Jr. et al., US 2689854 (1954 to Pfizer). Characterization, similarity to aureothricin, q.v.: W. D. Celmer et al., J. Am. Chem. Soc. 74, 6304 (1952). Structure: W. D. Celmer, I. A. Solomons, ibid. 77, 2861 (1955). Total synthesis: U. Schmidt, F. Geiger, Ann. 664, 168 (1963); K. Hagio, N. Yoneda, Bull. Chem. Soc. Jpn. 47, 1484 (1974). Bactericidal, protozoicidal, fungicidal properties: H. Seneca et al., Antibiot. Chemother. 2, 357 (1952). Mode of action: A. Jimenez et al., Antimicrob. Agents Chemother. 3, 729 (1973). Inhibition of microbiological growth in beer: J. B. Bockelmann, F. B. Strandskov, US 2798811 (1957 to Schaefer Brewing Co.). Activity against soil borne pathogens: P. R. Deb, B. K. Dutta, Curr. Sci. 53, 659 (1984). As allergy inhibitor: P. Stahl et al., DE 3434562 (1986 to Boehringer, Mannheim), C.A. 105, 54609k (1986).

Chemical structure

Properties

Brilliant yellow needles from n-butanol, dec 273-276°. Sublimes 200°/0.1 mm. uv max (methanol): 250, 311, 388 nm (ε 6300, 5700, 11,000) (Celmer, Solomons). Sparingly sol in water (210 mg/l); more sol in methanol, ethanol, chloroform, acetone (1% solns in acetone have been prepd), glacial acetic acid, methyl isobutyl ketone. Less sol in ether, benzene, hexane. Stable in acid and neutral solns, decomp in alkaline soln. Effective vs gram-positive and gram-negative bacteria, fungi and ameboid parasites. LD50 in mice (mg/kg): 25 s.c.; 25 orally (Seneca).