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Branched-chain alpha-keto-acid dehydrogenase system inhibitor and preparation method and application thereof

A catalyst and solvate technology, applied in the field of chemistry, can solve problems such as complex structure of compounds, no application value, and difficult synthesis, and achieve the effect of simple and easy control of the reaction operation process, favorable for mass preparation, and high synthesis efficiency

Active Publication Date: 2018-12-11
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

T-1 and T-2 are a class of high-efficiency inhibitors against pyruvate dehydrogenase in microorganisms. However, these compounds have complex structures and are difficult to synthesize, and such analogs of thiamine pyrophosphate have not yet been shown to be effective in agriculture. Applied value

Method used

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  • Branched-chain alpha-keto-acid dehydrogenase system inhibitor and preparation method and application thereof
  • Branched-chain alpha-keto-acid dehydrogenase system inhibitor and preparation method and application thereof
  • Branched-chain alpha-keto-acid dehydrogenase system inhibitor and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050]

[0051] Preparation of compound 1:

[0052] Dissolve 1mmol of 2-methyl 4-amino-5-methylpyrimidine azido and 1mmol of 4-chloroquinazolone amine propyne in 6ml of tert-butanol and water (volume ratio of tert-butanol to water=2:1) Add 0.01 mmol of copper sulfate pentahydrate and 0.1 mmol of sodium ascorbate to the solvent, react at room temperature for 12-24 hours, add 50 ml of water to the reaction system, stir to precipitate solids, suction filter, and dry to obtain yellow solids. Yield 86%, mp 222-224°C;

[0053] 1 H NMR (400MHz, DMSO-d 6 )δ(ppm): 2.29(s,3H),5.22(s,2H),5.38(s,2H),6.87(s,2H), 7.56(d,J=8.7Hz,1H),7.73(s, 1H), 8.10(s, 2H), 8.56(s, 1H);

[0054] HRMS (ESI): calcd.for C 17 h 15 ClN 8 O[M+H] + 383.11301, found: 383.11267.

[0055] Compound 2-14 was prepared in a similar manner to compound 1, and its structural identification data are as follows.

Embodiment 2

[0057]

[0058] The obtained pure product is a white solid with a yield of 89%, m.p.209-211°C;

[0059] 1 H NMR (400MHz, DMSO-d 6 )δ(ppm): 2.29(s,3H),5.23(s,2H),5.38(s,2H),6.87(s,2H), 7.69(s,1H),7.83(s,1H),8.07( d,J=23.3Hz,2H),8.54(s,1H);

[0060] HRMS (ESI): calcd.for C 17 h 15 ClN 8 O[M+H] + 383.11301, found: 383.11274.

Embodiment 3

[0062]

[0063] The obtained pure product is a white solid with a yield of 82%, m.p.133-135°C;

[0064] 1 H NMR (400MHz, DMSO-d 6 )δ(ppm): 2.29(s,3H),5.18(s,2H),5.39(s,2H),6.88(s,2H), 7.57(d,J=22.6Hz,2H),7.72(s, 1H), 8.12(s,1H), 8.54(s,1H);

[0065] HRMS (ESI): calcd.for C 17 h 15 ClN 8 O[M+H] + 383.11301, found: 383.11292.

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Abstract

The invention provides a compound and a preparation method and an application thereof, in particular a compound as shown in a formula I or a stereisomer, a geometrical isomer, tautomer, a despinner, anitric oxide, a hydrate, a solvate and pharmaceutical acceptable salt, wherein R1 is hydrogen or halogen and X is C or N; and R2 is a mono-substituent or a poly-substituent in any positions of a benzene ring, and the substituents can be same or different. The compound can be used for inhibiting growth of algae. The formula I is as shown in the description.

Description

technical field [0001] The present invention relates to the field of chemistry. Specifically, the present invention relates to compounds and their preparation methods and uses. More specifically, the present invention relates to compounds represented by formula I and their derivatives and their preparation methods and uses. Background technique [0002] At present, the research on the creation of new pesticides pays great attention to the pesticide active compounds with new structures and new targets. Pyruvate dehydrogenase complex can catalyze the conversion of pyruvate in organisms into acetyl-CoA, which is a key enzyme connecting glycolysis and citric acid cycle, and also a key enzyme in the energy metabolism process in organisms. Therefore, the rational design of pesticide molecules targeting the pyruvate dehydrogenase complex, an important agronomically important target, is of high research value. At present, some pyruvate dehydrogenase inhibitors have been reported, f...

Claims

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Application Information

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IPC IPC(8): C07D403/14A01N43/647A01N43/707A01P21/00A01P13/00
CPCA01N43/647A01N43/707C07D403/14
Inventor 贺红武周圆冯江涛冯玲玲
Owner HUAZHONG NORMAL UNIV
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