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Pyruvate dehydrogenase inhibitor type compound as well as preparation method and application thereof

A pyruvate dehydrogenase system and compound technology, applied in the field of chemistry, can solve the problems of complex structure, no application value, difficult synthesis, etc.

Active Publication Date: 2019-03-22
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, this type of compound has a complex structure and is difficult to synthesize, and this type of thiamine pyrophosphate analogue has not yet shown its application value in agriculture

Method used

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  • Pyruvate dehydrogenase inhibitor type compound as well as preparation method and application thereof
  • Pyruvate dehydrogenase inhibitor type compound as well as preparation method and application thereof
  • Pyruvate dehydrogenase inhibitor type compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Preparation of Compound 1

[0067]

[0068] Dissolve 1mmol of 2-methyl 4-amino-5-formylpyrimidine and 1.5mmol of benzohydrazide in 15mL of methanol solvent, add 0.02mmol of glacial acetic acid, heat and stir for 3-5h, monitor the reaction process by TLC, after the reaction is completed Add 50ml of water, stir and a solid precipitates out, filter with suction, and dry to obtain a white solid. Yield 78%, m.p.>260°C;

[0069] 1 H NMR (400MHz, DMSO-d 6 )δ(ppm):2.38(s,3H,CH 3 ),7.53(s,2H,NH 2 ),7.58(s,1H,Ar-H),7.92(d,2H,Ar-H,J=4.9Hz),8.07(s,1H,pyrimidine-H),8.42(s,1H,CH=N) ,8.42(s,2H,Ar-H),12.08(s,1H,NH);

[0070] 13 C NMR (100MHz, DMSO-d 6 )δ (ppm): 166.99, 163.17, 160.01, 158.30, 146.27, 133.16, 132.06, 128.69, 127.84, 107.31, 25.78;

[0071] ESI-MS m / z:256.2[M+1] + .

Embodiment 2

[0074]

[0075] The obtained pure compound 2 was a white solid with a yield of 89%, m.p.>260°C;

[0076] 1 H NMR (400MHz, DMSO-d 6 )δ(ppm):2.38(s,3H,CH 3 ),7.38(s,2H,NH 2 ),7.99(s,1H,pyrimidine-H),7.99(s,2H,Ar-H),8.41(s,1H,CH=N),8.41(s,2H,Ar-H),12.08(s, 1H,NH);

[0077] 13 C NMR (100MHz, DMSO-d 6 )δ (ppm): 166.92, 163.10, 161.96, 159.88, 158.27, 146.24, 130.49, 129.47, 115.73, 115.52, 107.15, 25.67;

[0078] ESI-MS m / z:274.3[M+1] + .

Embodiment 3

[0080]

[0081] The obtained pure compound 3 was a yellow solid with a yield of 68%, m.p.>260°C;

[0082] 1 H NMR (400MHz, DMSO-d 6 )δ(ppm):2.35(d,3H,CH 3 ,J=34.5Hz),7.46(s,2H,NH 2 ),7.52(d,1H,Ar-H,J=6.4Hz),7.58(d,1H,Ar-H,J=6.4Hz),8.03(s,1H,pyrimidine-H),8.19(s,1H ,CH=N),8.25(s,2H,Ar-H),8.29(s,2H,Ar-H),12.14(s,1H,NH);

[0083] 13 C NMR (100MHz, DMSO-d 6 )δ (ppm): 162.50, 159.94, 159.43, 158.63, 146.60, 134.99, 131.73, 130.61, 129.95, 129.56, 127.50, 106.95, 25.78;

[0084] ESI-MS m / z:290.1[M+1] + .

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Abstract

The invention provides a pyruvate dehydrogenase inhibitor type compound, as well as a preparation method and application thereof, and particularly provides to a compound shown as a formula I or a stereisomer, geometrical isomer, tautomer, racemate, oxynitride, hydrate, solvate and pharmaceutically-acceptable salt thereof, wherein R1 and R2 are independently selected from hydrogen, alkyl, amino orcarbocyclic group; R3 is a single-substituted or multi-substituted group at any position of a benzene ring; the substituted group can be the same or different; X is an acylhydrazone group or a hydrazone group. The compound has the activity of restraining pyruvate dehydrogenase, and can prevent and / or treat plant diseases and inhibit algae growth. The formula I is shown in the description.

Description

technical field [0001] The present invention relates to the field of chemistry. Specifically, the present invention relates to compounds, preparation methods and applications thereof. More specifically, the present invention relates to compounds represented by formula I, derivatives, preparation methods and applications thereof. Background technique [0002] Exploring and discovering pesticide active compounds that not only have new structures but also have new targets is the focus of current research on the creation of new pesticides. In the metabolic process of organisms, the pyruvate dehydrogenase complex can catalyze the conversion of pyruvate in the organism into acetyl-CoA, which is the key enzyme connecting glycolysis and citric acid cycle, and also the key enzyme in the energy metabolism process in the organism . Therefore, the pyruvate dehydrogenase complex is a target with important agronomic significance, and the rational design of pesticide molecules targeting t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/42C07D239/48C07D405/12A01N43/54A01N47/30A01P1/00A01P3/00A01P13/00
CPCA01N43/54A01N47/30C07D239/42C07D239/48C07D405/12
Inventor 贺红武周圆
Owner HUAZHONG NORMAL UNIV