Title: Thiolutin
CAS Registry Number: 87-11-6
CAS Name: 6-(Acetamido)-4-methyl-1,2-dithiolo[4,3-b]pyrrol-5(4H)-one
Additional Names: 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
Molecular Formula: C8H8N2O2S2
Molecular Weight: 228.29
Percent Composition: C 42.09%, H 3.53%, N 12.27%, O 14.02%, S 28.09%
Literature 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).
Properties: Brilliant yellow needles from n-butanol, dec 273-276°. Sublimes 200°/0.1 mm. uv max (methanol): 250, 311, 388 nm (e 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).
Absorption maximum: uv max (methanol): 250, 311, 388 nm (e 6300, 5700, 11,000) (Celmer, Solomons)
Toxicity data: LD50 in mice (mg/kg): 25 s.c.; 25 orally (Seneca) |