RESUMO
A novel approach to the production of chiral 1,3-cyclohexadienals has been developed. The organocatalysed asymmetric reaction of different ß-disubstituted-α,ß-unsaturated aldehydes with a chiral α,ß-unsaturated aldehyde in the presence of a Jørgensen-Hayashi organocatalyst provides easy and stereocontrolled access to the cyclohexadienal backbone. This method allows for the synthesis of potential photoprotective chiral 1,3-cyclohexadienals and extra extended conjugation compounds in a simple manner.
Assuntos
Aldeídos/química , Cicloexenos/síntese química , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Cristalografia por Raios X , Cicloexenos/química , Modelos Moleculares , Espectroscopia de Prótons por Ressonância Magnética , Espectrometria de Massas por Ionização por Electrospray , EstereoisomerismoRESUMO
Several sesterterpenolides analogues of dysidiolide have been synthesized and their in vitro antitumoural activity against human HeLa, A549, HT-29 and HL-60 carcinoma cells is presented. The proliferation inhibition data showed a significant antitumour activity of the compounds 1b, 2a, 2b, 3a, 3b, 4a, 4b, 5, inhibiting proliferation of distinct cancer cell types with an IC(50) in the low micromolar range.
Assuntos
4-Butirolactona/análogos & derivados , Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Terpenos/química , 4-Butirolactona/síntese química , 4-Butirolactona/química , 4-Butirolactona/farmacologia , Aldeídos/química , Antineoplásicos/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Humanos , Hidroxilação , Cetonas/química , Modelos Moleculares , Estrutura Molecular , Sesterterpenos , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
The bioactive sesterterpenoid gamma-hydroxybutenolides 15,18-bisepi-ent-Cladocoran A and B, 1 and 2, and 15-epi-ent-Cladocoran A and B, 57 and 55, were synthesized from ent-halimic acid. The synthesized sesterterpenolids 2, 55, 57, and 59 inhibited cellular proliferation (IC(50) congruent with 2 micro M) of a number of human leukaemic and solid tumor cell lines.