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Synthetic method and application of 1, 6-dihydro pyridazine and pyridazine compounds in inhibition of growth activity of five common pathogenic fungis

Technology of a compound, pyridazine salt, applied in the field of chemistry

Inactive Publication Date: 2015-10-07
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

By reviewing the known methods, we found that the direct construction of 1,6-dihydropyridazine compounds through the intramolecular radical cyclization reaction of β, γ-unsaturated hydrazones using visible light-catalyzed strategy is simple and mild. , has not been reported in the literature

Method used

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  • Synthetic method and application of 1, 6-dihydro pyridazine and pyridazine compounds in inhibition of growth activity of five common pathogenic fungis
  • Synthetic method and application of 1, 6-dihydro pyridazine and pyridazine compounds in inhibition of growth activity of five common pathogenic fungis
  • Synthetic method and application of 1, 6-dihydro pyridazine and pyridazine compounds in inhibition of growth activity of five common pathogenic fungis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Compound I-1

[0062]

[0063] At room temperature, starting material β, γ-unsaturated hydrazone A-1 (117.0mg, 0.3mmol), 1.0 equivalent of 2,2,6,6-tetramethylpiperidine oxide (46.9mg, 0.3mmol), 1.5 Equivalent inorganic base potassium carbonate (62.2mg, 0.3mmol) and 2mol% photocatalyst Ru(bpy) 3 Cl 2 ·6H 2 O (4.5mg, 0.006mmol) was dissolved in anhydrous chloroform, and the trace oxygen in the solvent was removed under the protection of argon. Then react at room temperature under the irradiation condition of the blue LED lamp of 3W until TLC detects that the reaction is complete, with V 石油醚 / V 乙酸乙酯 =20:1-10:1 column chromatography directly obtains the target product of formula I-1 with a yield of 84%.

[0064] 1 H NMR (600MHz, CDCl 3 )δ(ppm)δ=7.95(d,J=8.2Hz,2H),7.81–7.81(m,2H),7.57(d,J=7.0Hz,2H),7.47–7.44(m,3H),7.43– 7.42 (m, 3H), 7.38 (d, J=8.1Hz, 2H), 6.81 (s, 1H), 4.36 (s, 2H), 2.45 (s, 3H).

[0065] 13 C NMR (100MHz, CDCl 3 ) δ (ppm) δ = 150.71, 144.27, ...

Embodiment 2

[0069] Compound I-2

[0070]

[0071] At room temperature, starting material β, γ-unsaturated hydrazone A-2 (121.2mg, 0.3mmol), 1.0 equivalent of 2,2,6,6-tetramethylpiperidine oxide (46.9mg, 0.3mmol), 1.5 An equivalent amount of inorganic base potassium carbonate (62.2mg, 0.3mmol) and 2mol% photocatalyst (4.5mg, 0.006mmol) were dissolved in anhydrous chloroform, and trace oxygen in the solvent was removed under the protection of argon. Then react at room temperature under the irradiation condition of a blue LED light of 3W until the TLC detection reaction is complete, directly obtain the target product of formula I-2 with V petroleum ether / V ethyl acetate=20:1-10:1 column chromatography, product The rate is 85%. 1 H NMR (600MHz, CDCl 3 )δ(ppm)δ=7.91(d,J=8.1Hz,2H),7.66(d,J=8.0Hz,2H),7.52(d,J=7.7Hz,2H),7.40–7.33(m,3H ),7.33(d,J=8.0Hz,2H),7.20(d,J=8.0Hz,2H),6.76(s,1H),4.30(s,2H),2.40(s,3H),2.37(s ,3H).

[0072] 13 C NMR (100MHz, CDCl 3 ) δ (ppm) δ = 150.77, 144.26, 139....

Embodiment 3

[0075] Compound I-3

[0076]

[0077] At room temperature, starting material β, γ-unsaturated hydrazone A-3 (127.2mg, 0.3mmol), 1.0 equivalent of 2,2,6,6-tetramethylpiperidine oxide (46.9mg, 0.3mmol), 1.5 An equivalent amount of inorganic base potassium carbonate (62.2mg, 0.3mmol) and 2mol% photocatalyst (4.5mg, 0.006mmol) were dissolved in anhydrous chloroform, and trace oxygen in the solvent was removed under the protection of argon. Then react at room temperature under the irradiation conditions of a 3W blue LED lamp until the TLC detection reaction is complete, and directly obtain the target product of formula I-3 with V petroleum ether / V ethyl acetate=20:1-10:1 column chromatography, producing The rate is 74%.

[0078] 1 H NMR (600MHz, CDCl3) δ (ppm) δ = 7.93 (d, J = 7.9Hz, 2H), 7.73 (d, J = 8.2Hz, 2H), 7.56 (d, J = 6.7Hz, 2H), 7.48 -7.45 (m, 3H), 7.39 (t, J=9.1Hz, 4H), 4.36 (s, 2H), 2.45 (s, 3H).

[0079] 13 C NMR (100MHz, CDCl3) δ(ppm) δ=149.67, 144.42, 140.09, ...

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Abstract

The present invention provides a synthetic method and application of 1, 6-dihydro pyridazine and pyridazine compounds in inhibition of growth activity of five common pathogenic fungis, the compounds are a compound shown as the formula I, a pyridazine compound shown as the formula III, or enantiomers, diastereoisomers, racemes, pharmaceutically acceptable salts, crystalline hydrates or solvate, wherein R1 is an optionally substituted aryl, optionally substituted benzyl or optionally substituted alkyl; R2 is an optionally substituted aromatic group; and R3 is p-toluenesulfonyl. The compound can be used in the treatment of related diseases caused by fungis.

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 applications. More specifically, the present invention relates to compounds represented by formula I and their derivatives and their preparation methods and applications. Background technique [0002] Pyridazine and its derivatives, as an important class of six-membered nitrogen-containing heterocyclic rings, are organic base compounds derived from the biological world, and widely exist in many active natural products, functional materials and some drug molecules with important biological activities . Because of their wide range of biological activities, pyridazine and its derivatives are considered to be the "advantageous structures" for discovering new drug molecules, and their efficient and selective synthesis has always attracted the research interests of many chemists and pharmacologists. [0003] The...

Claims

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Application Information

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IPC IPC(8): C07D237/04C07D403/04C07D409/04C07D237/08A61P31/10
CPCC07D237/04C07D237/08C07D403/04C07D409/04
Inventor 陈加荣胡小强肖文精严冬梅
Owner HUAZHONG NORMAL UNIV
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