7976. Pyridomycin

Nomenclature

CAS number: 18791-21-4
3-Hydroxy-N-[(2Z,5R,6S,9S,10S,11R)-10-hydroxy-5,11-dimethyl-2-(1-methylpropylidene)-3,7,12-trioxo-9-(3-pyridinylmethyl)-1,4-dioxa-8-azacyclododec-6-yl]-2-pyridinecarboxamide.
C27H32N4O8; mol wt 540.56.
C 59.99%, H 5.97%, N 10.36%, O 23.68%.

Description and references

Antimycobacterial antibiotic substance produced by Streptomyces albidofuscus Okami et Umezawa, nov sp., renamed S. pyridomyceticus. Isoln: Maeda et al., J. Antibiot. 6A, 140 (1953); K. Yagishita, ibid. 7A, 143 (1954). Degradation studies: Maeda, ibid. 10A, 94 (1957). Structure: Koyama et al., Tetrahedron Lett. 1967, 3587; H. Ogawara et al., Chem. Pharm. Bull. 16, 679 (1968). Synthetic study: M. Kinoshita, M. Awamura, Bull. Chem. Soc. Jpn. 51, 869 (1978); M. Kinoshita et al., ibid. 3595. Production: JP 54 7048; JP 55 1349; JP 56 9566 (1954, 1955, 1956 all to Nippon Antibiotic Subst. Sci. Assoc.).

Chemical structure

Properties

Crystals from ethanol, mp 222°. uv max (ethanol): 303 nm (E1%1cm 209). Soluble in lower alcohols, ethyl or butyl acetate, benzene, acetone, dioxane, tetrahydrofuran. Practically insol in water.

Derivative

Hydrochloride.

Properties

Crystals, mp 194-196°. Freely sol in water. [α]D16 -53.2° (water). pH of aq solns about 2.0. LD50 i.p. in mice: >2100 mg/kg (Yagishita).