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Matrix metalloprotease inhibitors and synthetic method thereof

A technology of protease inhibitors and matrix metals, applied in the field of matrix metalloproteinase inhibitors and synthesis, to achieve the effects of short synthesis process routes, easy availability of raw materials, and low production costs

Inactive Publication Date: 2008-10-08
NANCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since Gross and Lapierre discovered the collagenase (MMP-1) that can degrade the tail in tadpoles in 1962, there is still no ideal MMPs inhibitor for clinical application.

Method used

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  • Matrix metalloprotease inhibitors and synthetic method thereof
  • Matrix metalloprotease inhibitors and synthetic method thereof
  • Matrix metalloprotease inhibitors and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0025] Synthesis of benzenesulfonyl-D-alanine:

[0026]

[0027] Add 2.56ml (20mmol) of benzenesulfonyl chloride to 1.96g (22mmol) of D-alanine in Na 2 CO 3 solution (4.45gNa 2 CO 3 Dissolve in 30ml of water), under vigorous stirring, react at 70°C for 0.5hr. After the reaction was completed, cool in an ice bath, adjust the pH value to 2.5 with concentrated hydrochloric acid, put it in the refrigerator overnight, and precipitate a white precipitate, filter, wash the filter cake with a small amount of ice water, recrystallize with distilled water, and dry to obtain 1.58 g of the target product. : 34.5%, mp: 126-128°C, [α]=+32.2° (0.025g / ml methanol solution, room temperature) (R)-5-phenyl-N-((2-benzenesulfonamide)-1- Synthesis of oxy-propyl)-1,3,4-thiadiazol-2-amine

[0028]

[0029] Dissolve 1.37g (6mmol) benzenesulfonyl-D-alanine and 0.69g (6mmol) N-hydroxysuccinimide in dioxane, add DCC dioxane solution at room temperature, and react at room temperature for 4hr ,...

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Abstract

The invention discloses matrix metalloproteinase inhibitors with general formula(I) and synthesis method thereof. The invention has the advantages that the compounds are all micro-molecular quasi-peptide compounds; the synthesis process is short, the material is easy to get, and the production cost is low.

Description

technical field [0001] The invention relates to a matrix metalloproteinase inhibitor and a synthesis method. Background technique [0002] With the intensification of the aging society and the increasing number of cancer patients around the world, the social and economic benefits of research and development of anti-tumor drugs with independent intellectual property rights are remarkable. Invasion and metastasis are the most prominent biological characteristics of malignant tumors and the main cause of clinical death in cancer patients. Matrix metalloproteinases (MMPs) are a class of important metalloproteinases that can catalyze the degradation of basement membrane and extracellular matrix. Inhibiting the activity of these enzymes can control the occurrence and metastasis of tumors. MMPs are a family of zinc-dependent endopeptidases that can degrade almost all components of the extracellular matrix. Studies have found that the invasion and metastasis of malignant tumor cel...

Claims

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Application Information

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IPC IPC(8): C07D285/135A61K31/433A61P35/00
Inventor 李少华涂国刚黄惠明熊芳匡滨海李东燕汪玢吴淑芳李刚
Owner NANCHANG UNIV
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