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CAS No 77392-58-6 , Spiro[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,2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-,(1'R,5'aS,7'R,8'aS,9'aR)-

  • Name: Spiro[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,2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-,(1'R,5'aS,7'R,8'aS,9'aR)-
  • Synonyms: Spiro[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,2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-,(1'R,5'aS,7'R,8'aS,9'aR)-; Paraherquamide A; [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; (-)-Paraherquamide A;Paraherquamide;(-)-Paraherquamide; VM 29919;Spiro[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,2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-, [1'R-(1'a,5'ab,7'b,8'ab,9'ab)]-;
  • CAS Registry Number:
  • Flash Point: 366.7°C
  • Boiling Point: 682.8°C at 760 mmHg
  • Density: 1.39g/cm3
  • Refractive index: 1.674
  • Flash Point: 366.7°C
  • Molecular Weight: 0
  • InChI: InChI=1/C28H35N3O5/c1-23(2)10-12-35-20-17(36-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31-11-9-25(5,34)28(31,22(33)30(26)6)13-18(26)24(27,3)4/h7-8,10,12,18,34H,9,11,13-15H2,1-6H3,(H,29,32)/t18-,25+,26+,27+,28-/m0/s1
  • Molecular Formula: C28H35 N3 O5
  • Molecular Structure:CAS No:77392-58-6 Spiro[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,2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-,(1'R,5'aS,7'R,8'aS,9'aR)-

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77392-58-6 PARAHERQUAMIDE A

  • Germany Cfm Oskar Tropitzsch [Manufacturer]
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References of Spiro[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,2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-,(1'R,5'aS,7'R,8'aS,9'aR)-
Title: Paraherquamide
CAS Registry Number: 77392-58-6
Synonyms: (-)-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.