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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

Active Publication Date: 2011-07-06
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the research on the asymmetric conjugate addition reaction based on tertiary amine-thiourea organic small molecule catalyst has been greatly developed, the research on its application range is still in progress; although curcumin analogues have good Pharmacological activity, however, no published reports on the synthesis of chiral curcumin analogues

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0048] Preparation Example 1 Synthesis of tertiary amine-thiourea catalyst

[0049] ,

[0050] Dissolve (S,S)-1,2-diphenylethylenediamine (2.12g, 10.0 mmol) in 40 mL of anhydrous tetrahydrofuran, add triethylamine (2.78mL) under ice-water bath; mL of 4-nitrobenzenesulfonyl chloride (2.21g, 10.0 mmol) in anhydrous tetrahydrofuran was slowly added dropwise to the above mixture; after the dropwise addition was completed, it was stirred at room temperature for 12 hours, the mixture was removed from the solvent under reduced pressure, and the residue was chromatographed on a silica gel column. (Petroleum ether? Ethyl acetate = 1?1) 3.34 g of white solid was obtained by separation, and the yield was 84%;

[0051] The above product (1.07, 2.7 mmol) was dissolved in 40 mL of anhydrous THF, and 40 mL of quinine-derived isothiocyanate (1 g, 2.7 mmol) in anhydrous THF was added dropwise under an ice-water bath Stir at room temperature for 12 hours after the dropwise addition, TLC d...

preparation Embodiment 2

[0054] Preparation Example 2 Synthesis of tertiary amine-thiourea catalyst

[0055] The difference from Preparation Example 1 is that the benzenesulfonyl protecting group used is 3,5-bistrifluoromethylphenylsulfonyl, other experimental methods and conditions are the same as in Example 1, and the final product is a white solid. The yield is 84% ​​(product configuration is S, S, S; R 1 for quinine, R 2 , R 3 is phenyl, R 4 is 3,5-bistrifluoromethylbenzenesulfonyl), its structural formula is:

[0056] ,

[0057] 1 H NMR (400 MHz, (CD 3 ) 2 CO): δ (ppm) 8.66 (d, J = 4.4 Hz, 1H), 8.03-7.93 (m, 5H), 7.48 (m, J = 4.4 Hz, 1H), 7.39-7.36 (m, 1H), 7.10 -7.02 (m, 5H), 6.94-6.90 (m, 5H), 5.86-5.77 (m, 3H), 5.01-4.89 (m, 3H), 3.97 (s, 3H), 3.29-3.23 (m, 3H) , 2.77-2.70 (m, 2H), 2.34 (br, 1H), 1.76-1.65 (m, 3H), 1.41-1.35 (m, 1H), 1.08-1.03 (m, 1H). 13 C NMR (100 MHz, (CD 3 ) 2 CO): Δ (PPM) 205.4, 183.5, 170.1, 157.6, 147.5, 144.8, 141.8, 138.1, 136.8, 131.7, 131.5, 128.3, ...

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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.

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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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/45C07C201/12C07D307/46C07B53/00B01J31/02C07D453/04
Inventor 叶金星李文军吴文彬于峰梁鑫淼
Owner EAST CHINA UNIV OF SCI & TECH
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