398. Amicoumacin A

Nomenclature

CAS number: 78654-44-1
3-Amino-2,3-dideoxy-N6-[1-(3,4-dihydro-8-hydroxy-1-oxo-1H-2-benzopyran-3-yl)-3-methylbutyl]hexaramide.
C20H29N3O7; mol wt 423.46.
C 56.73%, H 6.90%, N 9.92%, O 26.45%.

Description and references

Major component of a complex of antibiotics produced by Bacillus pumilus BN-103. Also exhibits anti-inflammatory activity in vivo. Isoln and biol activity: JP Kokai 83 18379 (1983 to Meiji Seika), C.A. 99, 20906x (1983); J. Itoh et al., J. Antibiot. 34, 611 (1981); eidem, Agric. Biol. Chem. 46, 1255 (1982). Structure: eidem, ibid. 2659. Use as acaricide: JP Kokai 83 216107 (1983 to Meiji Seika), C.A. 100, 116494b (1984).

Chemical structure

Derivative

Hydrochloride.

Properties

Colorless powder, mp 132-135° (dec). uv max (methanol): 208, 247, 315 nm (ε 27300, 6400, 4380). [α]D23 97.2° (c = 1.0 in methanol). LD50 orally in mice: 132 mg/kg (Itoh).