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Peptide analogue juvenile hormone synthesis inhibitor containing phenylpropyl alcohol-glycerol-bright tripeptide fragment

A technology of juvenile hormones and inhibitors, which is applied in the direction of peptides, biocides, chemical sterilants, etc., can solve the problems of unsatisfactory activity of tripeptide fragments, and achieve good development and application prospects, good inhibitory activity, and easy synthesis.

Inactive Publication Date: 2009-09-02
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with the activity of natural AST, the activity of tripeptide fragments is still not ideal

Method used

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  • Peptide analogue juvenile hormone synthesis inhibitor containing phenylpropyl alcohol-glycerol-bright tripeptide fragment
  • Peptide analogue juvenile hormone synthesis inhibitor containing phenylpropyl alcohol-glycerol-bright tripeptide fragment
  • Peptide analogue juvenile hormone synthesis inhibitor containing phenylpropyl alcohol-glycerol-bright tripeptide fragment

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1、D1

[0022] Synthesis of Preparation Example 1, D1 compound

[0023] (1) Resin activation: Weigh 200mg Rink Amide-AM resin, wash 4 times with DCM, add 15ml DCM to swell and activate for 3 hours, wash 4 times with DMF, add 20% piperidine DMF solution to cut for 20min, wash 4 times with 5ml DMF, 5ml DCM washed 4 times, Kaiser's reagent detection.

[0024] (2) Connect with Leu: DMF wash 3 times, add 106mg Fmoc-Leu-OH (3 times the amount), 114mg HBTU (3 times the amount), 41mg HOBt (3 times the amount), 105ul DIEA (6 times the amount), dissolve in 15ml DMF, stirred at room temperature for 2h, washed 4 times with 5ml DMF, cut by adding 20% ​​piperidine DMF solution for 20min, washed 4 times with 5ml DMF, washed 4 times with 5ml DCM, detected by Kaiser's reagent.

[0025] (3) Connect to Gly: wash 3 times with DMF, add 90mg Fmoc-Gly-OH, 114mg HBTU, 41mg HOBt, 105ul DIEA, dissolve in 15ml DMF, stir at room temperature for 2h, wash 4 times with 5ml DMF, add 20% piperidine DMF solution Cut...

preparation Embodiment 2、D47

[0031] Synthesis of Preparation Example 2, D47 compound

[0032] (1) Resin activation: Weigh 200mg Rink Amide-AM resin, wash 4 times with DCM, add 15ml DCM to swell and activate for 3 hours, wash 4 times with DMF, add 20% piperidine DMF solution to cut for 20min, wash 4 times with 5ml DMF, 5ml DCM washed 4 times, Kaiser's reagent detection.

[0033] (2) Connect with Leu: DMF wash 3 times, add 106mg Fmoc-Leu-OH (3 times the amount), 114mg HBTU (3 times the amount), 41mg HOBt (3 times the amount), 105ul DIEA (6 times the amount), dissolve in 15ml DMF, stirred at room temperature for 2h, washed 4 times with 5ml DMF, cut by adding 20% ​​piperidine DMF solution for 20min, washed 4 times with 5ml DMF, washed 4 times with 5ml DCM, detected by Kaiser's reagent.

[0034] (3) Connect to Gly: wash 3 times with DMF, add 90mg Fmoc-Gly-OH, 114mg HBTU, 41mg HOBt, 105ul DIEA, dissolve in 15ml DMF, stir at room temperature for 2h, wash 4 times with 5ml DMF, add 20% piperidine DMF solution Cu...

preparation Embodiment 3、D52

[0040] Synthesis of Preparation Example 3, D52 compound

[0041] (1) Resin activation: Weigh 200mg Rink Amide-AM resin, wash 4 times with DCM, add 15ml DCM to swell and activate for 3 hours, wash 4 times with DMF, add 20% piperidine DMF solution to cut for 20min, wash 4 times with 5ml DMF, 5ml DCM washed 4 times, Kaiser's reagent detection.

[0042] (2) Connect with Leu: DMF wash 3 times, add 106mg Fmoc-Leu-OH (3 times the amount), 114mg HBTU (3 times the amount), 41mg HOBt (3 times the amount), 105ul DIEA (6 times the amount), dissolve in 15ml DMF, stirred at room temperature for 2h, washed 4 times with 5ml DMF, cut by adding 20% ​​piperidine DMF solution for 20min, washed 4 times with 5ml DMF, washed 4 times with 5ml DCM, detected by Kaiser's reagent.

[0043] (3) Connect to Gly: wash 3 times with DMF, add 90mg Fmoc-Gly-OH, 114mg HBTU, 41mg HOBt, 105ul DIEA, dissolve in 15ml DMF, stir at room temperature for 2h, wash 4 times with 5ml DMF, add 20% piperidine DMF solution Cu...

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Abstract

The invention discloses a novel peptide analogue juvenile hormone synthesis inhibitor which has a structure general formula D: R-Phe-Gly-Leu-NH2, wherein the R stands for (substituted) benzoyl, (substituted) benzene acetyl, (substituted) hydrocinnamoyl, (substituted) butylbenzene, (substituted) benzene valeryl, (substituted) benzene hexanoyl, (substituted) benzene acryloyl, diacid, fatty acid, hydrophobic amino acid, or the like. For the compound with the formula D, a tripeptide fragment Phe-Gly-Leu-NH2 of AST is used as a primer, and an N-end modification method is adopted to obtain a novel peptide analogue compound containing Phe-Gly-Leu-NH2 tripeptide which has simple structure. The activity of most compounds with the formula D is superior to that of the tripeptide fragment Phe-Gly-Leu-NH2, and the activity of an individual compound is equal to or superior than the activity of core pentapeptide of the natural AST. In the further application study, the partial compounds with the formula D have better in-vivo activity, thereby being the novel peptide analogue juvenile hormone synthesis inhibitor.

Description

technical field [0001] The invention relates to a class of peptoid juvenile hormone synthesis inhibitors containing phenylpropanoid-glycerin-leupeptide fragments. Background technique [0002] Juvenile hormone (JH) is an important class of insect hormones. It regulates the growth and development of immature insects and the reproduction of adults. Scientists have developed a large series of insect growth regulators (IGRs) - juvenile hormone analogues by using JH as the lead. The main varieties of existing juvenile hormone analogues are: methoprene, triprene, hydroprene, kinoprene, fenoxycard, Pyriproxyfen (pyriproxyfen) and pyridoxone (NC-170) and so on. These commercialized pesticides have played an important role in integrated pest management. However, these pesticides are all juvenile hormone analogs in chemical structure, and there is a possibility of cross-resistance. Therefore, it is very necessary to research and develop other IGRs with novel structures to meet th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/087A01N37/46A01P23/00
Inventor 杨新玲开振鹏凌云谢勇黄娟斯蒂芬.斯.陶博张金蕊陈馥衡
Owner CHINA AGRI UNIV
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