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Six cyclic dipeptides used for wound healing

A wound repair and cyclic dipeptide technology, applied in the biological medicine field, can solve problems such as the application of cyclic dipeptide not seen before, and achieve the effects of good wound repair effect, obvious treatment effect and fast wound healing speed.

Inactive Publication Date: 2016-06-01
SICHUAN GOODDOCTOR PHARMA GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are no reports on the application of cyclic dipeptides synthesized from proline, phenylalanine, valine, histidine, tyrosine, and glycine in wound repair

Method used

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  • Six cyclic dipeptides used for wound healing
  • Six cyclic dipeptides used for wound healing
  • Six cyclic dipeptides used for wound healing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1 The preparation method of the cyclic dipeptide (cycloproline-phenylpropane dipeptide) described in the present invention

[0016] Main pharmaceutical reagents: phenylalanine, proline protected by Boc amino group

[0017] Process for preparing cyclic pro-phe dipeptide:

[0018] (1) Preparation of phenylalanine methyl ester hydrochloride: Add 10 g of phenylalanine to a mixture of an appropriate amount of methanol and thionyl chloride, and stir at room temperature for 24 hours. TLC traced the completion of the reaction, and the solvent was spin-dried under reduced pressure to obtain 14.5 g of phenylalanine methyl ester hydrochloride.

[0019] (2) Neutralization and condensation reaction: add phenylalanine methyl ester hydrochloride obtained in step (1), 20 g of proline protected by Boc amino group, 20 ml of pyridine, DMAP (4-di methylaminopyridine), after being completely mixed, under the protection of argon, add the (Boc) of anhydrous tetrahydrofuran 2 O, ...

Embodiment 2

[0022] Embodiment 2 The preparation method of the cyclic dipeptide (cyclic pro-pro dipeptide) described in the present invention

[0023] Main pharmaceutical reagents: proline, proline protected by Boc amino group

[0024] Process for preparing cyclic pro-pro dipeptide:

[0025] (1) Preparation of proline methyl ester hydrochloride: add 11 g of proline to a mixture of an appropriate amount of methanol and thionyl chloride, and stir at room temperature for 20 h. The completion of the reaction was tracked by TLC, and the solvent was spin-dried under reduced pressure to obtain 15.19 g of proline methyl ester hydrochloride.

[0026] (2) Neutralization and condensation reaction: add proline methyl ester hydrochloride obtained in step (1), proline 22g, pyridine 20ml, DMAP (4-dimethyl aminopyridine), after all mixing, add anhydrous tetrahydrofuran (Boc) under the protection of argon 2 O, stirred at room temperature for 12 hours. The completion of the reaction was tracked by TLC, ...

Embodiment 3

[0029] Embodiment 3 The preparation method of the cyclic dipeptide (cycloproline-valeric dipeptide) described in the present invention

[0030] Main pharmaceutical reagents: valine, proline protected by Boc amino group

[0031] Process for preparing cyclic pro-val dipeptide:

[0032] (1) Preparation of valine methyl ester hydrochloride: Add 10 g of valine to a mixture of an appropriate amount of methanol and thionyl chloride, and stir at room temperature for 18 hours. The completion of the reaction was tracked by TLC, and the solvent was spin-dried under reduced pressure to obtain 16.81 g of valine methyl ester hydrochloride.

[0033] (2) Neutralization and condensation reaction: Add valine methyl ester hydrochloride obtained in step (1), 20 g of proline protected by Boc amino group, 20 ml of pyridine, DMAP (4-dimethyl aminopyridine), after all mixing, add anhydrous tetrahydrofuran (Boc) under the protection of argon 2 O, stirred at room temperature for 10 hours. The compl...

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Abstract

The invention provides six cyclic dipeptides used for wound healing. The cyclic dipeptide is one of pro-phe, pro-pro, pro-val, pro-his, pro-tyr and pro-gly. The cyclic dipeptide has remarkable therapeutic effect on wound. Inhibition rate of acute and chronic gastric ulcer is high, wound healing speed of burns and scalds is fast, and scars are shallow.

Description

technical field [0001] The invention belongs to the field of biomedicine, in particular to a cyclic dipeptide used for wound repair. Background technique [0002] 2,5-diketopiperazines (DKP), also known as cyclic dipeptides. This type of compound is formed by the condensation and cyclization of two amino acids through peptide bonds. It is the smallest cyclic peptide compound in nature and widely exists in nature. It is found in humans, vertebrates, invertebrates, bacteria and fungi. There are discoveries. 2,5-diketopiperazines have two hydrogen bond donors and two hydrogen bond acceptors, because hydrogen bonds are one of the main ways for receptors to interact with drugs, so the six-membered ring of DKP is important in medicinal chemistry. DKP is an important pharmacophore, and many active natural products have been found to contain the six-membered ring structure of DKP, which has a variety of biological activities such as broad-spectrum antibacterial activity, antitumor...

Claims

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Application Information

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IPC IPC(8): C07K5/12C07K1/16C07K1/06A61P1/04A61P17/02
Inventor 耿福能
Owner SICHUAN GOODDOCTOR PHARMA GRP
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