1962. Cellocidin

Nomenclature

CAS number: 543-21-5
2-Butynediamide; acetylenedicarboxamide; acetylenedicarboxylic acid diamide; aquamycin; lenamycin.
C4H4N2O2; mol wt 112.09.
C 42.86%, H 3.60%, N 24.99%, O 28.55%.

Description and references

Antibiotic substance with antibacterial activity. Produced by Streptomyces chibaensis from soil collected at Chiba City, Japan: Suzuki et al., J. Antibiot. 11, 81 (1958). Synthesis from dimethyl acetylenedicarboxylate and concd ammonium hydroxide at -10°: Saggiomo, J. Org. Chem. 22, 1171 (1957); Suzuki, Okuma, J. Antibiot. 11, 84 (1958). Identity with lenamycin: Y. Sekizawa, Meiji Seika Kenkyu Nempo 1960, 42, C.A. 56, 14609a (1962). Biosynthesis: E. R. H. Jones, J. Chem. Soc. Perkin Trans. 1 1973, 148.

Chemical structure

Properties

Crystals from dil methanol, dec. 216-218°. uv max (0.1N NaOH): 299 nm (E1%1cm 290). Sparingly sol in water, methanol, ethanol, acetone, chloroform, glacial acetic acid. Relatively stable in neutral or acid solns, showing no loss of activity at pH 2 to 7 when heated for 10 min at 100°. Unstable in alkaline soln evolving ammonia. LD50 i.v. in mice: 11 mg/kg (Suzuki).