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Insect allatostatins pentapeptide analogue containing formylurea structure and application thereof

A technology of methyl and compound, which is applied in the field of pentapeptide analogues of insect pharyngeal inhibitors, can solve the problems of reduced activity, reduced biological activity, and increased molecular rigidity.

Active Publication Date: 2019-11-05
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

while analogue 2 (ED 50 =0.16μmol / L), analog 3 (ED 50 =0.80μmol / L), analog 4a (ED 50 =10μmol / L) and 4b(ED 50 =0.1-10 μmol / L) activity decreased by several orders of magnitude, the introduction of Cpa and Bzd increased the steric hindrance, increased the rigidity of the molecule, and greatly reduced the biological activity. It is speculated that Gly 7 During the design and synthesis of the site space, it is necessary to maintain a certain degree of molecular flexibility, and at the same time it is not easy to introduce larger groups
Nachman et al. also introduced phenylpropionic acid into the "core pentapeptide" and synthesized the analogue AST(b)φ2. The in vitro activity test results showed that the activity of AST(b)φ2 was reduced by 3 compared with the natural Dippu-AST 5. order of magnitude, but its metabolic stability in hemolymph, brain and hindgut has been greatly improved

Method used

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  • Insect allatostatins pentapeptide analogue containing formylurea structure and application thereof
  • Insect allatostatins pentapeptide analogue containing formylurea structure and application thereof
  • Insect allatostatins pentapeptide analogue containing formylurea structure and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The compound of formula A of the present invention is prepared according to the method of polypeptide solid-phase synthesis.

[0050] Taking compound A1 as an example, its preparation method is as follows:

[0051] (1) Resin activation: Weigh 440 mg Rink Amide-AM resin, activate it with 5 mL DCM for 3 h, add 20% piperidine in DMF solution, cut for 20 min, wash with DMF and DCM three times, and monitor the reaction with Kaiser’s reagent.

[0052] (2) Connecting to Leu: add Fmoc-Leu-OH (3 times equivalent), HBTU (3 times equivalent), HOBt (3 times equivalent), DIEA (6 times equivalent), dissolve in 5mLDMF, stir at room temperature for 2h, remove the reaction Solution, DMF and DCM were washed 3 times each, and Kaiser's reagent was used to monitor the reaction. Then add 20% piperidine in DMF solution for cutting for 20 min, and wash with DMF for 3 times.

[0053] (3) Connecting to Gly: add Fmoc-Gly-OH (3 times equivalent), HBTU (3 times equivalent), HOBt (3 times equivale...

Embodiment 2

[0065] Example 2 The in vitro inhibitory activity of the compounds of the present invention on the biosynthesis of juvenile hormone in the Pacific cockroach

[0066] The present invention adopts the GC-MS / MS bioassay method of Kai Zhenpeng et al. (reference: Kai, Z.P.; Yin, Y.; Zhang, Z.R.; Huang, J.; Tobe, S.S.; Chen, S.S.J. , 1538, 67). The newly emerged female adults were collected, and after the 7th day, they were dissected to obtain the pharyngeal body. The target compound was made into a 10mmol / L mother solution, which was sequentially diluted into 1mmol / L, 0.1mmol / L, 0.01mmol / L, 0.001mmol / L and 0.0001mmol / L assay solutions. Then use a 1-10uL pipette gun to take 10uL of different concentrations of the measurement solution and add it to a 1.5mL centrifuge tube containing 990uL M199 medium. After mixing well, the obtained concentrations are 0.01mmol / L, 0.001 mmol / L, 0.0001 mmol / L, 0.00001 mmol / L, and 0.000001 mmol / L. Measure 100uL of the prepared drug solution into smal...

Embodiment 3

[0068] Example 3 The activity of some compounds of the present invention on Plutella xylostella larvae at a concentration of 200mg / L is the same as that of the pentapeptide analogue of a class of insect depressantin in the control of Plutella xylostella according to any one of claims 1-3. application. The insecticidal activity screening method to diamondback moth is as follows: adopt leaf soaking method; under the concentration of 200mg / L, A6, A7 are initially screened for insecticidal activity to diamondback moth; -100 aqueous solution for dilution. Each concentration was repeated 4 times, with 30 test insects for each repetition, and a blank control was set up; the cabbage leaves that had grown straight were selected, immersed in 200mg / L liquid medicine for 5s, dried in the room for 2 hours, and placed in a 9cm-diameter The 2nd instar early larvae of Plutella xylostella of the same size were inserted into the culture dish. Check the results at 96 hours and calculate the co...

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Abstract

The invention belongs to the technical field of insecticides, and in particular, relates to an insect allatostatins pentapeptide analogue containing a formylurea structure and an application thereof.A compound represented by the formula A is proposed and has the following structure defined in the specification, wherein in the formula A, R is an aromatic ring or a substituted aromatic ring; the substituent group is a mono-substituted or multi-substituted halogen, nitro group, trifluoromethyl, cyano group, hydroxyl, methyl or methoxyl. The compound has a certain activity of inhibiting the growth of plutella xylostella larvae, is in line with the characteristics of insect growth regulators and has further application and development value.

Description

technical field [0001] The invention belongs to the technical field of insecticides, and in particular relates to a formylurea structure-containing insect pharyngeal side voxin pentapeptide analogue and its application Background technique [0002] Along with the use of traditional pesticides, 3R (resistance, re-rampant and residue) problems gradually emerged. Traditional pesticides are developing in the direction of green pesticides. Among them, insect growth regulators (IGRs) play an important role in integrated pest management because of their high efficiency, high selectivity, and environmental friendliness. Insect neuropeptides are a type of active small peptides that are periodically synthesized and secreted by specific neurosecretory cells in the insect brain and transmitted through nerves or hemolymph, which affect the growth, development, metamorphosis and other physiological processes of insects. Potential insect growth regulator. [0003] Allatostatins (ASTs) a...

Claims

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Application Information

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IPC IPC(8): C07K5/103C07K1/04A01N47/34A01P7/04
CPCA01N47/34C07K5/1008
Inventor 杨新玲汪梅子凌云开振鹏张怡萌金小宇
Owner CHINA AGRI UNIV
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