RESUMO
A facile novel strategy has been developed to obtain a key intermediate of squalamine, 7α, 24R -dihydroxy-5α-cholestan-3-one, starting from methyl Δ5-3ß-hydroxycholanate. The pure product was successfully synthesized and separated from the C-24 position epimers in good purity, d.e.% and yield.
Assuntos
Colestanonas/química , Colestanonas/síntese química , Técnicas de Química Sintética , Colestanóis/química , EstereoisomerismoRESUMO
A novel and practical preparation of 2-pyridone-containing tricyclic alkaloid derivatives was developed. By regioselective intramolecular N- and C-acylation of 2-(4-aryl-2-pyridon-6-yl)benzoic acid, a pair of structural isomers 2-aryl pyrido[2,1-a]isoindole-4,6-diones and 4-aryl 1-methyl-1H-indeno[1,2-b]-pyridine-2,5-diones, as potential inhibitors of tumor cell proliferation, were prepared respectively.
Assuntos
Alcaloides/síntese química , Antineoplásicos/síntese química , Inibidores do Crescimento/síntese química , Piridonas/síntese química , Acilação/efeitos dos fármacos , Alcaloides/farmacologia , Antineoplásicos/farmacologia , Proliferação de Células/efeitos dos fármacos , Inibidores do Crescimento/farmacologia , Piridonas/farmacologia , EstereoisomerismoRESUMO
A novel and practical procedure was developed for the abnormal Beckmann rearrangement of steroid 17-oximes. Treatment of the 17-oximes with TFA/CH(OMe)(3) in boiling THF for 2 h gives the corresponding 13,17-seco alkene nitrile products in unprecedented high yields (70-92%). Since the alkene nitriles can be subsequently converted into 18-norsteroids, this general method provides a highly efficient route to these biologically important compounds and, by extension, to other structurally related natural products.