异黄酮衍生物的合成及其活性研究

Synthesis of isoflavone Derivatives and Preliminary Studies on their Bioactivities

摘要:

以间苯二酚和对甲氧基苯乙酸为原料，在三氟化硼乙醚、N, N-二甲基甲酰胺和甲基磺酰氯作用下，采用超声波辐射技术“一锅法”合成了7-羟基-4’-甲氧基异黄酮 (Ⅰ)，收率为84.0％。然后将其分别与苯甲酰氯、乙酰氯、苯氧乙酰氯、肉桂酰氯和水杨酰氯成酯得到5个异黄酮衍生物(Ⅱa~e)，收率分别为57.1％、60.6%、59.4%、61.1%和50.4%。利用IR，H1 NMR，C13 NMR 和MS对Ⅱa~e的结构进行表征。体外抗骨质疏松活性实验表明：5种化合物对体外培养的乳鼠颅盖骨成骨细胞的生长有较好的促进作用。

Abstract:

Starting from resorcinol and p-methoxylphenylacetic, a facile one-pot synthesis of 7-Hydroxy-4’-methoxyl-isoflavone (Ⅰ) was achieved in 84.0％ yield under ultrasonic irradiation for the first time in the presence of boron trifluoride-diethyl ether, DMF and methanesulfonyl chloride. Then (Ⅰ) reacted with benzoyl chloride, acetyl chloride, 2-phenoxyacetyl chloride, cinnamoyl chloride and 2-hydroxybenzoyl chloride to give five isoflavone derivatives (Ⅱa~e) respectively in 57.1％, 60.6%, 59.4%, 61.1% and 50.4%. Their structures were confirmed by IR, H1 NMR, C13 NMR and MS spectroscopy. Finally the pharmacological assays of anti-osteoporosis indicated that these compounds could promote the proliferation of rat’s osteoblast in vitvo to a certain degree.