Paraherquamide
Title: Paraherquamide
CAS Registry Number: 77392-58-6
Additional Names: (-)-Paraherquamide; [1¢R-(1¢a,5¢ab,7¢b,8¢ab,9¢ab)]-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
Molecular Formula: C28H35N3O5
Molecular Weight: 493.59
Percent Composition: C 68.13%, H 7.15%, N 8.51%, O 16.21%
Literature 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).
Properties: Colorless prisms, mp 244-247° (dec). [a]D22 -28° (c = 0.43 in methanol). uv max (ethanol): 226, 260, 290nm (e 32400, 6100, 1600). Sol in methanol, ethyl acetate, acetone, DMSO. Practically insol in water.
Melting point: mp 244-247° (dec)
Optical Rotation: [a]D22 -28° (c = 0.43 in methanol)
Absorption maximum: uv max (ethanol): 226, 260, 290nm (e 32400, 6100, 1600)
Therap-Cat-Vet: Anthelmintic.

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