Azomycin is a small heterocyclic imidazole first isolated from a species of Nocardia by Umezawa’s group in 1953 as an antibiotic with activity against Gram positive and Gram negative species. The structure was resolved as 2-nitroimidazole in 1955 and readily synthesized from 2-aminoimidazole in 1965. Azomycin is present in other bacterial genera, Streptomyces and Pseudomonas. In 1956, it was reported to have antiprotozoan activity. Subsequent research focused on activity against anaerobic bacteria including Clostridium perfringens and Bacteroides fragilis.
- A new antibiotic, azomycin. Maeda K. et al., J. Antibiot. 1953, 6, 182.
- Production of tertiomycin (a new antibiotic substance), azomycin and eurocidin by S. eurocidicus. Osato T. et al., J. Antibiot. 1955, 8, 105.
- Structure of azomycin, a new antibiotic. Nakamura S., Pharm. Bull. 1955, 3, 379.
- Studies in the nitroimidazole series. I. Synthesis of azomycin and related compounds. Beaman A.G. et al., Antimicrob. Ag. Chemother. 1965, 469.
- Synthesis of azomycin. Beaman A.G. et al., J. Am. Chem. Soc. 1965, 87, 389.