7026. Paraherquamide

Nomenclature

CAS number: 77392-58-6
(-)-Paraherquamide; [1′R-(1′α,5′aβ,7′β,8′aβ,9′aβ)]-2′,3′,8′a,9′-tetrahydro-1′-hydroxy-1′,4,4,8′,8′,11′-hexamethylspiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7′(8′H)-[5H,6H-5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-9,10′(10H)-dione.
C28H35N3O5; mol wt 493.59.
C 68.13%, H 7.15%, N 8.51%, O 16.21%.

Description and references

Oxindole alkaloid fungal metabolite. Isolation from Penicillium paraherquei and structure: M. Yamazaki et al., Maikotokishin 10, 27 (1980), C.A. 95, 19321p (1981); M. Yamazaki et al., Tetrahedron Lett. 22, 135 (1981); from P. charlesii and nematocidal activity: J. G. Ondeyka et al., J. Antibiot. 43, 1375 (1990). Absolute stereochemistry: T. A. Blizzard et al., J. Org. Chem. 54, 2657 (1989). Approach to synthesis: R. M. Williams, T. D. Cushing, Tetrahedron Lett. 31, 6325 (1990). Anthelmintic activity in sheep: W. L. Shoop et al., J. Parasitol. 76, 349 (1990); in dogs: W. L. Shoop et al., Vet. Parasitol. 40, 339 (1991). Toxicity: eidem, Am. J. Vet. Res. 53, 2032 (1992). Mode of action: J. M. Schaeffer et al., Biochem. Pharmacol. 43, 679 (1992).

Chemical structure

Properties

Colorless prisms, mp 244-247° (dec). [α]D22 -28° (c = 0.43 in methanol). uv max (ethanol): 226, 260, 290nm (ε 32400, 6100, 1600). Sol in methanol, ethyl acetate, acetone, DMSO. Practically insol in water.

Therapeutic Category (Veterinary)

Anthelmintic.