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Alpha,beta-diamino acid derivative and synthetic method and application thereof

A technology of diamino acid and synthetic method, applied in the field of alpha, can solve the problems of unfriendly environment, high cost, poor universality of substrates, etc.

Inactive Publication Date: 2012-05-02
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention overcomes the deficiencies such as poor substrate universality, high cost and unfriendly environment existing in the preparation method of α, β-diamino acid derivatives in the prior art, and proposes an α, β-diamino acid derivative and its Synthetic method and application, the synthetic method of the present invention has the advantages of environmental friendliness, low cost, high yield, mild reaction conditions, good selectivity, wide substrate applicability, safe and simple operation, etc.

Method used

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  • Alpha,beta-diamino acid derivative and synthetic method and application thereof
  • Alpha,beta-diamino acid derivative and synthetic method and application thereof
  • Alpha,beta-diamino acid derivative and synthetic method and application thereof

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Comparison scheme
Effect test

Embodiment 1

[0064]

[0065] Ethyl glyoxylate (0.20mmol, 1.0eq), PhNH 2 (0.44mmol, 2.2eq), Rh 2 (OAc) 4 (0.004mmol), chiral phosphoric acid (0.01mmol) and Molecular sieves (100mg) were dissolved in toluene (1.0ml) at room temperature and stirred for 10min; then, diazoacetophenone (0.24mmol, 1.2eq) dissolved in toluene (1.0ml) was added dropwise within 1 hour Into the reaction system, after the dropwise addition, stir for 20 minutes. The reaction product was subjected to column chromatography (ethyl acetate:petroleum ether=1:15~1:10) to obtain a pure product. The structure of the product is shown in formula 3-1. The yield was 95%, the dr value was greater than 90:10, and the ee value was 95%.

[0066] Wherein, the chiral phosphoric acid substituent R is triphenylsilyl.

[0067] 1 H-NMR (500MHz, CDCl 3 ): 8.00(d, J=6.5Hz, 2H), 7.63(m, 1H), 7.52(d, J=6.5Hz, 2H), 7.16-7.21(m, 4H), 6.78-6.81(m, 4H) , 6.61-6.63(m, 2H), 5.54-5.56(m, 1H), 4.79(d, 2H), 4.62-4.68(m, 2H), 4.04(m, 2H), 1....

Embodiment 2

[0069]

[0070] Ethyl glyoxylate (0.2mmol, 1.0eq), P-ClPhNH 2 (0.44mmol, 2.2eq), Rh 2 (OAc) 4 (0.004mmol), chiral phosphoric acid (0.01mmol) and Molecular sieves (200mg) were dissolved in toluene (1.0ml) at room temperature and stirred for 10min; then, diazoacetophenone (0.24mmol, 1.2eq) dissolved in toluene (3.0ml) was added dropwise within 1 hour Into the reaction system, after the dropwise addition, stir for 20 minutes. The reaction product was subjected to column chromatography (ethyl acetate:petroleum ether=1:15~1:10) to obtain a pure product. The structure of the product is shown in formula 3-2. The yield was 90%, the dr value was greater than 90:10, and the ee value was 94%.

[0071] Wherein, the chiral phosphoric acid substituent R is triphenylsilyl.

[0072] 1 H-NMR (400MHz, CDCl 3 ): 7.95-7.97(m, 2H), 7.62-7.66(m, 1H), 7.49-7.52(m, 2H), 7.11-7.17(m, 2H), 7.08-7.09(m, 2H), 6.70-6.73 (m, 2H), 6.51-6.54(m, 2H), 5.45-5.49(m, 1H), 4.76(d, J=10.2Hz, 1H), 4.64(...

Embodiment 3

[0074]

[0075] Ethyl glyoxylate (0.2mmol, 1.0eq), p-BrPhNH 2 (0.44mmol, 2.2eq), Rh 2 (OAc) 4 (0.004mmol), chiral phosphoric acid (0.01mmol) and Molecular sieves (150mg) were dissolved in toluene (1.0ml) at room temperature and stirred for 10min; then, diazoacetophenone (0.24mmol, 1.2eq) dissolved in toluene (2.0ml) was added dropwise within 1 hour Into the reaction system, after the dropwise addition, stir for 20 minutes. The reaction product was subjected to column chromatography (ethyl acetate:petroleum ether=1:15~1:10) to obtain a pure product. The structure of the product is shown in formula 3-3. The yield was 89%, the dr value was greater than 90:10, and the ee value was 92%.

[0076] Wherein, the chiral phosphoric acid substituent R is triphenylsilyl.

[0077] 1 H-NMR (500MHz, CDCl 3 ): 7.95(d, 2H), 7.62-7.65(m, 1H), 7.49-7.52(m, 2H), 7.28(d, J=8.7Hz, 2H), 7.23(d, J=8.7Hz, 2H) , 6.65(d, J=8.7Hz, 2H), 6.47(d, J=8.7Hz, 2H), 5.46-5.48(m, 1H), 4.78(d, J=10.1Hz,...

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Abstract

The invention discloses a synthetic method of an alpha, beta-diamino acid derivative. In the method, a one-step reaction is undergone by taking a diazo compound, aniline and aldehyde acid ester as raw materials, taking metal Lewis acid and chiral phosphoric acid as catalysts, taking an organic solvent as a solvent and taking a 4 Angtrom molecular sieve as a water absorbing agent, so that the alpha, beta-diamino acid derivative is obtained. The synthetic method disclosed by the invention has the advantages of high atom economy, high selectivity and high yield, the reaction conditions are mild, and operation is easy and safe. The alpha, beta-diamino acid derivative has anticancer activity and structural diversity, and is suitable for preparing and applying antitumor, antibiotic and antifungal medicaments.

Description

technical field [0001] The invention belongs to the field of synthetic medicine and chemical industry, and mainly relates to an α, β-diamino acid derivative and its synthesis method and application. Background technique [0002] α, β-Diamino acid derivatives are a kind of important skeleton structures for building natural products and synthetic drugs, and many marine organisms and natural antibiotics contain such skeleton structures. For example, there are such skeleton structures in many drug structures such as antineoplastic drugs bleomycin and peplomycin, and tuberculosis drug viomycin. α,β-Diamino acid derivatives can also be used in the synthesis of numerous other antineoplastic drugs, antibiotics, antifungal drugs. In addition, α,β-diamino acid derivatives can be used as ligands (Inorg. Biochem. 1995, 57, 279.) and synthetic building blocks to synthesize a series of biologically active compounds. In addition, it has a strong chelation effect with metals, and this pro...

Claims

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Application Information

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IPC IPC(8): C07C229/36C07C227/10C07C229/28C07C229/26C07B53/00A61P35/00A61P31/10A61P31/00
Inventor 胡文浩荆常诚钱宇周静张霞孙照栓杨琍苹
Owner EAST CHINA NORMAL UNIV
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