RESUMO
Potassium aeshynomate (1) is the leaf-opening factor of the nyctinastic plant Aeshynomene indica L. In this article a convenient and efficient strategy for the total synthesis of enantiomerically pure 1 is described, starting from the l-arabinose derived chiron ent-6. The realized synthetic scheme involves a postcoupling oxidation approach and securely determines the absolute configuration of the targeted natural product, which remained unknown until now.
Assuntos
Azadirachta/química , Butiratos/síntese química , Fenóis/síntese química , Butiratos/química , Conformação Molecular , Fenóis/química , Folhas de Planta/química , EstereoisomerismoRESUMO
The synthesis of novel pyrimidine deoxyapiothionucleosides of D- and L-series was realized following application of a versatile and high-yielding scheme, which utilized inexpensive L- and D-arabinose as starting materials, respectively, and which makes use of a regio- and stereo-selective Pummerer rearrangement reaction for the coupling of the nucleobase with the thiosugar moiety. Some of the targeted compounds have shown selective cytotoxic effects (with IC50<10 µM) against specific cancer cell lines. All of the tested compounds had no cytotoxic effect on the normal cell line tested.
Assuntos
Antineoplásicos/síntese química , Pirimidinas/química , Tionucleosídeos/química , Antineoplásicos/química , Antineoplásicos/toxicidade , Arabinose/química , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Células HT29 , Células HeLa , Humanos , Células MCF-7 , Relação Estrutura-Atividade , Tionucleosídeos/síntese química , Tionucleosídeos/toxicidadeRESUMO
An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4-enals and hex-5-en-ones-2 followed by N-O bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.