Synthesis and Medicinal Significance of Chalcones- A Review

Chavan Bb, Gadekar As, Mehta Pp, P. Vawhal, Kolsure Ak, Chabukswar Ar
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引用次数: 45

Abstract

Chalcone is an aromatic ketone that forms a central core for a variety of important biological compounds, which are collectively known as chalcones. They possess different activities like antibacterial, antifungal, anti-inflammatory and anti tumor etc depending on the substitution made on them. Chalcones are 1,3-diphenyl-2-propene-1-one, in which two aromatic rings are linked by a three carbon α, β-unsaturated carbonyl system.These are abundant in edible plants and are considered to be precursors of flavonoids and isoflavonoids. Chalcones possess conjugated double bonds and a completely delocalized Π-electron system on both benzene rings. Molecules possessing such system have relatively low redox potentials and have a greater probability of undergoing electron transfer reactions. The compounds with the backbone of chalcones have been reported to possess various biological activities such as antimicrobial, anti-inflammatory, analgesic, anti platelet, anti ulcerative, anti malarial, anticancer, antiviral, anti leishmanial, antioxidant, anti tubercular, anti hyperglycemic, immunomodulatory, inhibition of chemical mediators release, inhibition of leukotriene B4, inhibition of tyrosinase and inhibition of aldose reductase activities. The presence of a reactive alpha, beta -unsatutated keto function in chalcones is found to be responsible for their antimicrobial activity. In this paper through reviewing different biological significance of chalcones and their derivatives have been reported along with their chemistry and of synthesis. Synthetically or chemically chalcones are synthesized by two reactions: a) Aldol condensation and b) Claisen Schmidt condensation. But here is a focus on chalcones synthesized by Claisen Schmidt condensation which involves the condensation between an aromatic aldehyde or ketone with an aliphatic ketone or aldehyde catalysed by the presence of dilute alkali or acid to form alpha beta unsaturated compound.
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查尔酮的合成及药用意义综述
查尔酮是一种芳香酮,它构成了多种重要生物化合物的核心,这些化合物统称为查尔酮。它们具有不同的抗菌、抗真菌、抗炎、抗肿瘤等活性,这取决于它们的替代作用。查尔酮是1,3-二苯基-2-丙烯-1- 1,其中两个芳香环由三碳α, β-不饱和羰基体系连接。它们在可食用植物中含量丰富,被认为是类黄酮和异黄酮的前体。查尔酮在两个苯环上具有共轭双键和完全离域Π-electron体系。具有这种体系的分子具有相对较低的氧化还原电位,并且具有较大的发生电子转移反应的概率。以查尔酮为骨架的化合物具有抗菌、抗炎、镇痛、抗血小板、抗溃疡、抗疟疾、抗癌、抗病毒、抗利什曼原虫、抗氧化、抗结核、抗高血糖、免疫调节、抑制化学介质释放、抑制白三烯B4、抑制酪氨酸酶和醛糖还原酶活性等多种生物活性。在查尔酮中存在的反应性α, β -不饱和酮功能被发现是其抗菌活性的原因。本文综述了查尔酮及其衍生物的不同生物学意义以及它们的化学性质和合成方法。人工合成或化学合成查尔酮有两个反应:a) Aldol缩合和b) Claisen Schmidt缩合。但这里重点讲的是用Claisen Schmidt缩合法合成的查尔酮它是芳香族醛或酮与脂肪族酮或醛在稀碱或稀酸的催化下缩合形成不饱和化合物。
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