Allopumiliotoxin_267A Knowpia

Allopumiliotoxin 267A
Nombre IUPAC
	(7R,8R,8aS)-8-Methyl-6-[(2R)-2-methylhexylidene]-1,2,3,5,7,8a-hexahydroindolizine-7,8-diol
General
Fórmula estructural
Fórmula molecular	H; 29NO; 2
Identificadores
Número CAS	73376-38-2
ChEBI	182171
ChEMBL	CHEMBL2002405
ChemSpider	4580699
PubChem	5470308
UNII	TEP57TLJ38
	SMILES O[C@@H]1C(=C\[C@H](C)CCCC)\CN2[C@H]([C@]1(O)C)CCC2
	InChI InChI=1S/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1; Key: LWXKAVPXEDNHLL-VRUXTKGDSA-N
Propiedades físicas
Masa molar	267,41 g/mol
	Valores en el SI y en condiciones estándar; (25 ℃ y 1 atm), salvo que se indique lo contrario.
	[editar datos en Wikidata]

Allopumiliotoxin 267A es una toxina que se encuentra en la piel de varias ranas venenosas de la familia Dendrobates.^[2] Es un miembro de la clase de compuestos conocidos como allopumiliotoxinas . Las ranas producen la toxina mediante la modificación de la versión original, pumiliotoxin 251D.^[3] Se ha probado en ratones y comprobado que es cinco veces más potente que la versión anterior. Se ha producido sintéticamente a través de una variedad de rutas diferentes.^[4]^[5]^[6]^[7]

Referencias

↑ Número CAS
↑ Edwards MW, Daly JW, Myers CW. Alkaloids from a panamanian poison frog, Dendrobates speciosus: identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine. Journal of Natural Products. 1988 Nov-Dec;51(6):1188-97. PMID 3236011
↑ Daly JW, Garraffo HM, Spande TF, Clark VC, Ma J, Ziffer H, Cover JF Jr. Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates. Proceedings of the National Academy of Sciences USA. 2003 Sep 16;100(19):11092-7. PMID 12960405
↑ Comins DL, Huang S, McArdle CL, Ingalls CL. Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: a concise asymmetric synthesis of (+)-allopumiliotoxin 267A. Organic Letters. 2001 Feb 8;3(3):469-71. PMID 11428041
↑ Franklin AS, Overman LE. Total Syntheses of Pumiliotoxin A and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies. Chemical Reviews 1996;96(1),505-522.
↑ Tang XQ, Montgomery J. Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B. Journal Of The American Chemical Society. 2000;122(29):6950-6954.
↑ Aoyagi S, Wang TC, Kibayashi C. Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/chromium(II)-mediated cyclization. Journal of the American Chemical Society 1993;115(24):11393-11409.

Enlaces externos

Esta obra contiene una traducción derivada de «Allopumiliotoxin 267A» de Wikipedia en inglés, publicada por sus editores bajo la Licencia de documentación libre de GNU y la Licencia Creative Commons Atribución-CompartirIgual 4.0 Internacional.

Datos: Q530596

[1] Número CAS

[2] Edwards MW, Daly JW, Myers CW. Alkaloids from a panamanian poison frog, Dendrobates speciosus: identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine. Journal of Natural Products. 1988 Nov-Dec;51(6):1188-97. PMID 3236011

[3] Daly JW, Garraffo HM, Spande TF, Clark VC, Ma J, Ziffer H, Cover JF Jr. Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates. Proceedings of the National Academy of Sciences USA. 2003 Sep 16;100(19):11092-7. PMID 12960405

[4] Comins DL, Huang S, McArdle CL, Ingalls CL. Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: a concise asymmetric synthesis of (+)-allopumiliotoxin 267A. Organic Letters. 2001 Feb 8;3(3):469-71. PMID 11428041

[5] Franklin AS, Overman LE. Total Syntheses of Pumiliotoxin A and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies. Chemical Reviews 1996;96(1),505-522.

[6] Tang XQ, Montgomery J. Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B. Journal Of The American Chemical Society. 2000;122(29):6950-6954.

[7] Aoyagi S, Wang TC, Kibayashi C. Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/chromium(II)-mediated cyclization. Journal of the American Chemical Society 1993;115(24):11393-11409.

[2]

[3]

[4]

[5]

[6]

[7]

[1]

Summary

Referencias

Enlaces externos