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Amino acid-hydroxamic acid aminopeptidase N inhibitor and preparation method thereof

A hydroxime and aminopeptidase technology, which is applied in the field of amino acid hydroxamic acid aminopeptidase N inhibitors and synthesis, can solve the problems of reducing the antigen recognition ability of T cells, reducing the immune function of the body, and accelerating tumor metastasis and deterioration. , to achieve the effect of short synthesis process route, low production cost and rapid reaction

Inactive Publication Date: 2018-11-16
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This technology allows for easy access to specific chemicals by creating them quickly at an affordable price level without requiring complicated or expensive methods like chemistry.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding novel treatments targeting certain proteins involved with inflammatory processes like autoimmunology or neurology (such as brain glial cells). These targets include cytokines associated with these pathologies, including IL-17A/F, GM1 gangli protein-1β(GMP1), laminin receptor 2B-55 (LAR2), α7 nicotype adhesion molecule 1 (α 7), insolubility factor-2 alpha (INF) ligand 3 (INFL-3), EPO, etc., among others.

Method used

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  • Amino acid-hydroxamic acid aminopeptidase N inhibitor and preparation method thereof
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  • Amino acid-hydroxamic acid aminopeptidase N inhibitor and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Preparation of the target compound (compound 7a in Table 1).

[0025] (1) Preparation of cinnamoyl-D-alanine ④.

[0026] Dissolve 22.5mmol of cinnamic acid and 24mmol of N-hydroxysuccinimide in 35ml of anhydrous dioxane, and add 24mmol of dicyclohexylcarbodiimide in anhydrous dioxane solution, and react at room temperature for 6 After 1 hour, a white precipitate was formed, and the precipitate was filtered off. The filtrate was slowly added to an aqueous solution containing 24 mmol D-alanine and 24 mmol sodium bicarbonate, and a large amount of white solid precipitated out. The temperature was raised to 50° C., and refluxed for 24 hours. After the reaction is complete, evaporate most of the solvent, add a small amount of water to dissolve the residue and filter out the insoluble matter, adjust the pH of the water phase to 2 with 2mol / L concentrated hydrochloric acid, place it in the refrigerator overnight, and precipitate a white precipitate, filter and dry, ...

Embodiment 2

[0029] Example 2: Preparation of (R)-3-(2-chlorophenyl)-N-(1-methyl-2-hydroxyamino-2-carbonylethyl)-acrylamide (7c).

[0030] The target compound 7c was prepared by the same method, white solid, yield: 80.1%; melting point: 150-152 °C; 1 H-NMR (600MHz, DMSO-d 6 )δ10.71(s,1H,OH),8.89(s,1H,NH),8.33(d,J=7.9Hz,NH),7.62(d,J=5.6Hz,2H),7.42(d,J =15.8Hz,1H),7.26(t,J=8.8Hz,2H),6.71(d,J=15.8Hz,1H),4.37-4.32(m,J=7.1Hz,1H),1.24(d,J =7.0Hz, 3H); IR (KBr), ν: 3152, 3028, 2341, 1616, 1400, 1118, 690cm -1 ;ESI-MS: m / z[M-H] - 267.1.

Embodiment 3

[0031] Example 3: Preparation of (R)-4-fluoro-N-(1-methyl-2-hydroxyamino-2-carbonylethyl)-benzamide (8a).

[0032] The target compound 8a was prepared by the same method, white solid, yield: 76.6%; melting point: 151-153°C; 1 H-NMR (600MHz, DMSO-d 6 )δ8.33(d, J=7.8Hz, NH), 7.28(dd, J=8.6,5.7Hz, 2H), 7.10(d, J=8.9Hz, 2H), 4.41-4.36(m, J=7.1 Hz, 1H), 3.44(s, 1H), 1.18(d, J=7.1Hz, 3H).IR(KBr), ν: 3445, 3174, 2341, 1631, 1542, 1400, 1242, 853cm -1 ;ESI-MS: m / z[M-H] - 225.1.

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Abstract

The invention provides an amino acid-hydroxamic acid aminopeptidase N inhibitor and a preparation method thereof. The amino acid-hydroxamic acid aminopeptidase N inhibitor has a general chemical formula which is described in the specification. In the general chemical formula, R1 is selected from the group consisting of H, CH3 and CH2CH(CH3)2; R2, R3 and R4 are selected from the group consisting ofH, F, Cl, Br, OCH3, CH3 and CH(CH3)3; and n is equal to 0 or 1. According to the invention, an amide intermediate is obtained by condensation of substituted benzoic acid, substituted phenylacetic acid or substituted cinnamic acid with glycine, R-alanine or R-valine; and an amino acid-hydroxamic acid final product is generated by a reaction of the amide intermediate with isobutyl chloroformate andhydroxylamine hydrochloride through a mixed anhydride method. The preparation method provided by the invention has the advantages of mild reaction conditions, short process route, easily-available raw materials and low production cost.

Description

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Claims

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Application Information

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Owner NANCHANG UNIV
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