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Novel juvenile hormone synthesis inhibitor-phenylpropyl alcohol-glycerol-bright tripeptide amide analogue

A juvenile hormone and tripeptide amide technology, which is applied in the fields of peptides, biocides, and pest control, can solve the problems of high synthesis cost and complex structure, and achieve the effects of simple structure, good inhibitory activity, and good development and application prospects

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

These literatures have modified the structure of AST by mimicking peptidology. Most of the analogues have complex structures (simulating active peptides above pentapeptide), and the synthesis cost is high, so they are not suitable for development as new pesticides.

Method used

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  • Novel juvenile hormone synthesis inhibitor-phenylpropyl alcohol-glycerol-bright tripeptide amide analogue
  • Novel juvenile hormone synthesis inhibitor-phenylpropyl alcohol-glycerol-bright tripeptide amide analogue
  • Novel juvenile hormone synthesis inhibitor-phenylpropyl alcohol-glycerol-bright tripeptide amide analogue

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1、B1

[0022] Synthesis of Preparation Example 1, B1 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 with 20% piperidine DMF solution for 20min, washed 4 times with 5ml DMF, 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 for 20min, wa...

preparation Embodiment 2、B4

[0030] The synthesis of preparation embodiment 2, B4 compound

[0031] (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.

[0032] (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.

[0033] (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 soluti...

preparation Embodiment 3、B7

[0038] The synthesis of preparation embodiment 3, B7 compound

[0039] (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.

[0040] (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.

[0041] (3) Receive succinic anhydride: wash 3 times with DMF, add 30 mg succinic anhydride and 37 mg DMPA, dissolve in 15 ml DMF, stir at room temperature for 2 h, wash 4 times with 5 ml DMF, 4 times with 5 ml DCM, and...

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Abstract

The invention discloses a juvenile hormone synthesis inhibitor with novel structure, which is a phenylpropyl alcohol-glycerol-bright tripeptide amide analogue. The structure general formula of the compound provided by the invention is B: R-Leu-NH2, wherein the R stands for Phe-Gly-, Tyr-Gly-, PhCH2CH2CO-Gly-, PhCH=CHCO-Gly-, Ph(CH2)5CO-, Ph(CH2)4CO-, PhCH2NHCO(CH2)2CO-, PhCH2NHCO(CH2)3CO- or PhCH2NHCOCH2CO-. The compound with formula B simulates the chemical structure of a PHe-Gly-Leu-NH2 fragment of an A type AST and has simple structure and low synthesis cost. The compound has better inhibition activity for the juvenile hormone synthesis of black beetles. In the further application study, the compound obviously influences reproductive systems of female black beetles, inhibits the generation of black beetle eggs, conforms to the characteristic of an insect growth regulator and has better development and application prospects.

Description

technical field [0001] The present invention relates to a new class of juvenile hormone inhibitors-phenylpropanol-glycerin-leupeptide amide analogs. Background technique [0002] Insect neuropeptides are a class of active small peptides that are periodically synthesized and secreted by specific neurosecretory cells in the insect brain and transmitted through nerves or body fluids. Insect neuropeptides coordinate with each other, control and regulate the activities of certain organs or glands of insects, and affect important physiological processes such as growth, development, metamorphosis, reproduction and metabolism of insects. In the past three decades, with the development of chemistry and biology, especially the wide application of advanced analytical methods, a large number of insect neuropeptides have been discovered, such as prothoracicotropichormone (PTTH), prothoracicostatic peptide, PTSP), allatotropin (AT), allatostatin (AST), diapause hormone (DH), pheromone bi...

Claims

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Application Information

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IPC IPC(8): C07K5/087C07K5/097C07K5/078A01N37/46A01P23/00
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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