RESUMO
Several prenylflavonoids have been synthesised and tested against human tumour cell lines. The prenyl unit has been geranyl or a labdane diterpene. These labdane-flavonoids have been synthesised for the first time. The antitumour activity increase with the prenylation at C-8 position. Twenty-three C and O-prenylated acylphloroglucinols have been synthesised as well. In this case the C-alkylation products have resulted, in general, more active.
Assuntos
Acetofenonas/síntese química , Acetofenonas/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Flavonoides/síntese química , Flavonoides/farmacologia , Acetofenonas/química , Antineoplásicos/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Flavonoides/química , Humanos , Concentração Inibidora 50 , Análise EspectralRESUMO
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
[Reaction: see text]. The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, was obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.
Assuntos
Poríferos/química , Sesquiterpenos/síntese química , Terpenos/síntese química , Aldeídos/química , Animais , Diterpenos/química , Conformação Molecular , Estrutura Molecular , Oxirredução , Fotoquímica , Estereoisomerismo , Terpenos/químicaRESUMO
Incubation of sclareol with Rhizopus stolonifer affords in high yield a mixture of triols with 18-hydroxy-sclareol as the main component.
Assuntos
Diterpenos/metabolismo , Rhizopus/metabolismo , Diterpenos/química , HidroxilaçãoRESUMO
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.
Assuntos
Antineoplásicos/síntese química , Terpenos/síntese química , Terpenos/farmacologia , 4-Butirolactona/análogos & derivados , 4-Butirolactona/química , 4-Butirolactona/farmacologia , Antineoplásicos/farmacologia , Divisão Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Humanos , Concentração Inibidora 50 , Proteínas Tirosina Fosfatases/antagonistas & inibidores , Sesterterpenos , Estereoisomerismo , Relação Estrutura-AtividadeRESUMO
Two new diterpenic acids with an ent-halimane skeleton have been isolated from the aerial parts of Halimium viscosum (Villarino de los Aires chemotype) and separated as methyl esters. These diterpenes were 13-oxo-14, 15-dinor-1(10),11E-ent-halimadien-18-oic acid and 15-hydroxy-1(10),13Z-ent-halimadien-18-oic acid.
