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Compound capable of effectively inhibiting or killing multi-drug resistant bacteria and preparation method and application of compound

A compound, aldol condensation reaction technology, applied in the field of medicine, can solve problems such as drug-resistant bacteria

Active Publication Date: 2016-11-23
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the long-term use of these compounds, resistant bacteria have also emerged

Method used

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  • Compound capable of effectively inhibiting or killing multi-drug resistant bacteria and preparation method and application of compound
  • Compound capable of effectively inhibiting or killing multi-drug resistant bacteria and preparation method and application of compound
  • Compound capable of effectively inhibiting or killing multi-drug resistant bacteria and preparation method and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0205] Embodiment 1, preparation compound D3

[0206]

[0207] 1. Preparation of intermediate α, β-unsaturated ketone a

[0208] The specific operation steps are as follows: add 20.0 mL of absolute ethanol to a round bottom flask, cool to 0°C with an ice-water bath, add 1.10 mL (10 mmol) of 3-acetylpyridine and 1.00 mL (10 mmol) of 5-methylfurfural, and dissolve 480 mg Solid sodium hydroxide was dissolved in a mixture of 10.0 mL ethanol and 10.0 mL water, and the sodium hydroxide solution was added dropwise to the substrate solution, and reacted for 2 hours. Add saturated ammonium chloride solution to adjust the reaction solution to neutrality, add 100ml water to dilute, then extract 3 times with dichloromethane (adding 25ml dichloromethane each time), combine the organic phases extracted three times, wash twice with water Dry with anhydrous sodium sulfate, then spin dry the solvent under reduced pressure, and pass the residue through a silica gel column with petroleum eth...

Embodiment 2-15

[0220] According to the method basically the same as in Example 1, it is only necessary to replace 3-acetylpyridine or 5-methylfurfural in Step 1 of Example 1 and phenylhydrazine in Step 2 accordingly, and other operations are the same as in Example 1 , to obtain the following compound.

[0221]

[0222] 4-(5-(5-methylfuran-2-yl)-1-phenyl-1H-pyrazol-3-yl)pyridine

[0223] 1 H-NMR (400MHz, CDCl 3 )δ (ppm) 8.628 (d, J = 5.12Hz, 2H), 7.756 (d, J = 5.12Hz, 2H), 7.428-7.464 (m, 5H), 7.006 (s, 1H), 5.906 (d, J =2.52Hz, 1H), 5.782(d, J=3.16Hz, 1H), 2.284(s, 3H);

[0224] 13 C-NMR (100MHz, CDCl 3 )δ (ppm) 152.94, 150.27, 149.34, 142.25, 140.34, 140.11, 136.84, 129.21, 129.00, 126.20, 120.14, 110.22, 107.52, 102.96, 13.55;

[0225] LC-MS (ESI + ): m / z calculated for C 19 h 16 N 3 O(M+H) + :302.13, found 302.22.

[0226]

[0227] 2-(5-(5-methylfuran-2-yl)-1-phenyl-1H-pyrazol-3-yl)pyridine

[0228] 1 H-NMR (400MHz, CDCl 3 )δ (ppm) 8.659 (d, J = 4.74Hz, 1H), 8.046 (d,...

Embodiment 16

[0288] Example 16, preparation of compound D3-5

[0289]

[0290] Example 16 is similar to 1-15, but the preparation method of the intermediate hydrazone is different.

[0291] In Example 16, unsaturated ketones were prepared by aldol condensation, unsaturated hydrazones were generated by dehydration condensation catalyzed by concentrated sulfuric acid, and pyrazole products were generated by intramolecular carbon-nitrogen bond coupling catalyzed by transition metals.

[0292] Compound data are characterized as follows:

[0293] 1 H-NMR (400MHz, CDCl 3)δ (ppm) 9.108 (s, 1H), 8.617 (d, J = 4.44Hz, 1H), 8.318 (d, J = 8.80Hz, 2H), 8.203 (d, J = 7.92Hz, 1H), 7.689 ( d, J=8.84Hz, 2H), 7.379(dd, J=7.88Hz, J=4.84Hz, 1H), 6.983(s, 1H), 6.256(d, J=3.16Hz, 1H), 6.064(d, J=3.12Hz, 1H), 2.300(s, 3H);

[0294] 13 C-NMR (100MHz, CDCl 3 )δ (ppm) 153.84, 150.40, 149.61, 147.39, 146.60, 145.03, 141.16, 136.21, 133.05, 128.19, 125.04, 124.45, 123.66, 111.72, 107.74, 105.45, 13.58;

...

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Abstract

The invention discloses a compound capable of effectively inhibiting or killing bacterial microorganisms. The compound has a structural general formula shown as the formula I (please see the formula in the description). Pharmacodynamic experiments prove that the compound can effectively inhibit or kill the broad-spectrum and multi-drug resistant staphylococcus aureus, streptococcus pneumoniae and staphylococcus aureus and is expected to be developed into a novel effective antibacterial drug with new targets.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a compound for effectively inhibiting or killing multidrug-resistant bacteria, a preparation method and application thereof. Background technique [0002] Antibiotics refer to the secondary metabolites of certain bacteria, actinomycetes, fungi and other microorganisms, or the same compounds or structural analogs synthesized by chemical methods, which are effective against various pathogenic microorganisms or tumor cells at low concentrations. Drugs with strong killing, inhibitory or other pharmacological effects. There are no less than 10,000 known natural antibiotics. China is a big country in the use and production of antibiotics. Due to the extensive use of antibiotics, China has become one of the countries with the most serious problem of antibiotic abuse in the world, and has led to the emergence of many drug-resistant bacteria, such as superbugs. [0003] Synthetic an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D409/14C07D401/14C07D401/04C07D231/12C07D405/06C07D405/04C07D231/16C07D231/18C07F9/6503A61K31/4439A61K31/497A61K31/415A61K31/4155A61K31/5377A61K31/675A61P31/04C07D409/06C07D401/06C07D307/54C07D307/46C07D307/52
CPCC07D231/12C07D231/16C07D231/18C07D307/46C07D307/52C07D307/54C07D401/04C07D401/06C07D401/14C07D405/04C07D405/06C07D405/14C07D409/06C07D409/14
Inventor 饶燏张敬仁胡建涛刘雪
Owner TSINGHUA UNIV
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