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4th phenylalaninamide hydroxylation modified endomorphin analogs and synthesis method and applications thereof

A phenylalanamide hydroxyl, endomorphin technology, applied in the direction of tetrapeptide components, drug combinations, peptide/protein components, etc., can solve cardiovascular system side effects, blood pressure reduction, affinity, opioid agonistic activity, and analgesia Features to be improved, etc.

Active Publication Date: 2018-05-04
黑龙江省工研院资产经营管理有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the affinity of endomorphins to μ-opioid receptors, opioid agonistic activity, and analgesic properties need to be improved
In addition, endomorphins can cause blood pressure reduction and bradycardia, which have certain side effects on the cardiovascular system.

Method used

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  • 4th phenylalaninamide hydroxylation modified endomorphin analogs and synthesis method and applications thereof
  • 4th phenylalaninamide hydroxylation modified endomorphin analogs and synthesis method and applications thereof
  • 4th phenylalaninamide hydroxylation modified endomorphin analogs and synthesis method and applications thereof

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specific Embodiment approach 1

[0076] Specific embodiment 1: The endomorphin analogue modified by the hydroxylation of the 4-phenylpropanamide in this embodiment is an endomorphin-1 analogue, tyrosine-proline-tryptophan-phenylpropanoid (N-hydroxyl) Amide, its structure is as follows:

[0077]

specific Embodiment approach 2

[0078] Specific embodiment two: the synthesis method of endomorphin analogs modified by hydroxylation of 4-phenylpropanamide in the present embodiment comprises the following steps:

[0079] One, the synthesis of N-tert-butoxycarbonyl-phenylpropanoid (N-hydroxyl) amide

[0080] Add N-tert-butoxycarbonyl-phenylalanine and N-hydroxysuccinimide into redistilled tetrahydrofuran, stir at 0-5°C to obtain reaction solution A; wherein N-tert-butoxycarbonyl-phenylalanine The molar ratio of N-hydroxysuccinimide is 1:1.2~1.4;

[0081] Dissolve N,N'-dicyclohexylcarbodiimide in tetrahydrofuran, add it to reaction solution A, stir and react at 0-5°C for 20-40 minutes, and then react at room temperature for 4-8 hours; where N-tert-butoxycarbonyl- The molar ratio of phenylalanine to N,N'-dicyclohexylcarbodiimide is 1:1.2~1.4;

[0082] Filter out the product 1,3-dicyclohexyl urea, retain the activated ester filtrate, dissolve hydroxylamine hydrochloride in water, adjust the pH value to 9-11,...

specific Embodiment approach 3

[0103] Specific embodiment three: the difference between this embodiment and specific embodiment two is: the washing method in step one is: wash with 5% citric acid solution, saturated sodium bicarbonate solution and saturated sodium chloride solution successively. Others are the same as in the second embodiment.

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Abstract

The invention discloses 4th phenylalaninamide hydroxylation modified endomorphin analogs and a synthesis method and applications thereof, relates to endomorphin analogs and a synthesis method and applications thereof, and provides 4th phenylalaninamide hydroxylation modified endomorphin analogs and a synthesis method and applications thereof. The endomorphin analogs are tyrosine-proline-tryptophan-phenylanine(N-hydroxyl)amide and tyrosine-proline-phenylalanine-phenylanine(N-hydroxyl)amide. The synthesis method comprises the following steps: step one, synthesizing N-t-butyloxycarboryl-phenylanine(N-hydroxyl)amide; step two, synthesizing phenylanine(N-hydroxyl)amide; step three, synthesizing carbobenzoxy-tryptophan-phenylanine(N-hydroxyl)amide; step four, synthesizing carbobenzoxy-tyrosine-proline-tryptophan-phenylanine(N-hydroxyl)amide; and step six, synthesizing tyrosine-proline-tryptophan-phenylanine(N-hydroxyl)amide. The analogs can be used to prepare polypeptide pain relieving drugs.

Description

technical field [0001] The present invention relates to endomorphin analogs and their synthesis methods and applications. Background technique [0002] Endomorphins are endogenous μ-opioid receptor ligands that widely exist in mammals and are divided into endomorphin-1 (Tyr-Pro-Trp-Phe-NH 2 , EM-1) and endomorphin-2 (Tyr-Pro-Phe-Phe-NH 2 ,EM-2). Among all known opioids, endomorphins have extremely high affinity and selectivity for μ-opioid receptors. Endomorphin participates in the regulation of many functions by binding to G protein-coupled μ-opioid receptors, but its main function is potent analgesic activity, which can produce analgesic effects with stronger activity than morphine and fewer side effects. Especially in animal models of neuropathic pain, it also shows obvious analgesic activity, which is more effective than most opioid peptides, making it a potential development prospect. Of course, based on the classical properties of the main chain backbone and aromat...

Claims

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Application Information

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IPC IPC(8): C07K5/107A61K38/07A61P25/04
CPCA61K38/00C07K5/1016
Inventor 王长林袁碧玉杨代军
Owner 黑龙江省工研院资产经营管理有限公司
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