Method for catalytically synthesizing chiral curcumin analogs

A curcumin analogue and chirality technology, which is applied in the field of catalytic synthesis of chiral curcumin analogues, can solve the problems that the research on the scope of application is still in progress, the synthesis of chiral curcumin analogues has no public reports, etc., and achieves novel structure. , Environmentally friendly, mild reaction conditions
CN102115446AActive Publication Date: 2011-07-06EAST CHINA UNIV OF SCI & TECH
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Patent Information

Authority / Receiving Office
CN ยท China
Patent Type
Applications(China)
Current Assignee / Owner
EAST CHINA UNIV OF SCI & TECH
Publication Date
2011-07-06
Patent Text Reader

Abstract

The invention relates to an asymmetric chemical reaction process of catalytic conjugate addition, in particular to a method for catalytically synthesizing chiral curcumin analogs. The method comprises the steps of: taking nitroolefin and curcumin analogs as raw materials; taking tertiary amine-thiourea organic catalyst as a catalyst system; reacting in dissolvent, wherein the reaction time is 0.5-15 days, and the reaction temperature is -40-40 DEG C; and generating a conjugate addition product. The reaction general formula is shown in the description: in the formula, R1 and R2 are aliphatic series group and aromatic series group. The structural formula of the tertiary amine-thiourea organic catalyst organic catalyst is shown in the description: in the formula, R1 is tertiary amine-containing quindenary derivative, R2 and R3 are different or same aromatic series substituent groups respectively, and R4 is sulfonyl substituent group. The tertiary amine-thiourea organic catalyst organic catalyst is high in catalytic activity and stereoselectivity in the Michael addition reaction between the nitroolefin and the curcumin analogs, wherein the enantioselectivity is highest to 97%, the yield is highest to 96%, and the reaction substrate is wide in range.
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Description

technical field

[0001] The invention relates to a chemical reaction process of asymmetric catalyzed conjugate addition, in particular to a method for catalyzing and synthesizing chiral curcumin analogues. Background technique

[0002] Curcumin is a phenolic pigment component in the rhizome of Turmeric, a plant of the genus Curcuma longa in the family Zingiberaceae. It is widely used as a toner and antioxidant in the food industry. With the development of society and the advancement of technology, people pay more and more attention to the development and utilization of natural biological resources. At present, the development of drugs based on natural products has become one of the hot spots in the field of drug research. Curcumin has attracted great interest from drug researchers because of its antibacterial, antioxidant, anti-inflammatory, anti-cancer, anti-HIV and other biological activities.

[0003] In recent years, articles and patent documents using curcumin as a lead...

Claims

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