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Synthesis Of Substituted 3-aryl-chromene-2-thiones Using KF/Al2O3 Meditated Method And Isoflavone Analogues Which Have Potent Aromatase Inhibition Activity

Posted on:2007-03-15Degree:MasterType:Thesis
Country:ChinaCandidate:X W XuFull Text:PDF
GTID:2144360182495926Subject:Medicinal chemistry
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Isoflavones, the effective constituents of many Chinese medicinal herb, are widely found in a number of plants. These natural products have demonstrated numerous biological activities such as antioxidant , anti-inflammatory , anticardiovascular, anticarcinogenic and aromatase inhibitory activities.3-aryl-chromene-2-thiones are important intermediates which can be easily transformed to isoflavones. Few literature have reported the synthesis of chromene-2-thiones analogs. They all need skillful handling of the base, low temperature, and anhydrous reaction conditions. Recently, a high yielding one-pot synthesis of 2-(alkylthio)isoflavone has been reported using NaOH as a base, Bu4NHSO4 as a phase-transfer catalyst, but the purification is troublesome. So we hope to find a method offers several advantages including the cheap starting materials, excellent yield, very facile purification.KF/Al2O3 taking the advantage of its strongly basic nature, is now replaced organic bases in a number of reactions. We reported herein that KF/Al2O3 efficiently catalyzed the conversion of deoxybenzoins and CS2 into 3-aryl-chromene-2-thiones. We still investigated the influence of the substituent group on the benzene .Compared with other method, this method have several advantage. By this method, 16 compounds were prepared.Isoflavones can prevent or relieve perimenopausal symptoms(osteoporosis, artherosclerosis and so on). many of pharmacological research demonstrate that the intake of Isoflavone are correlate with the proceed of breast carcinoma and the carcinoma of prostate. So it is significant to do structure modification and activity measurement to isoflavone. YOUNG W.K etal synthesized a series of Daidzin derivants and reported they have good aromatase inhibit activity. We synthesized 12 Daidzin and glycitin derivants and ready to measure and compare their aromatase inhibit activity.
Keywords/Search Tags:KF/Al2O3, 3-aryl-chromene-2-thiones, KF loaded on alumina, isoflavone, aromatase inhibit
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