Synthesis and cytotoxicity of some rigid derivatives of methyl 2,5-dihydroxycinnamate.
摘要：
Eight rigid compounds designed as esterase-stable analogues of methyl 2,5-dihydroxycin-namate (1) were synthesized. These derivatives include 2-(2′,5′-dihydroxybenzylidene)cyclo-pentenone ( 3a ), 2-(2′,5′;-dihydroxybenzylidene)cyclohexanone ( 3b ), 2,6-bis(2′,5′-dihydroxy-benzy-lidene)cyclohexanone ( 4b ), 2,6-bis(2′,5′-dihydroxybenzylidene)cyclopentenone ( 4a ), (E)-3-(2′,5′-dihydroxybenzylidene)pyrrolidin-2-one ( 5 ), ( E )-5-(2′,5′-dihydroxybenzylidene)-1,2-isothiazolidine-1, 1 -dioxide ( 6 ), 4-(2′,5′-dihydroxyphenyl)-5H-furan-2-one ( 7 ), and 3-(2′,5′-dihy-droxyphenyl)cyclopent-2-ene-1-one ( 8 ). Among the eight compounds, the furanone 7 and cyclopentenone 8 showed the most potent cytotoxicity with IC 50 values of 0.39-0.98 μg/mL Compound 8 was further brominated, phenylated and methylated at the α position to give three corresponding analogues, including 2-bromo-3-(2′,5′-dihydroxyphenyl)cyclopent-2-ene-1-one ( 24 ), 3-(2′,5′-dihydroxyphenyl)-2-phenylcyclopent-2-ene-1-one ( 27 ), and 3-(2′,5′-dihy-droxyphenyl)-2-methylcyclopent-2-ene-1-one ( 28 ). Among the three, the most enhanced activity was observed with the phenylated compound 27 .
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DOI：
10.1007/BF02976927
被引量：
年份：
2002
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