4-hydroxybenzoylacrylic acid derivative, preparation method thereof and application

A technology of hydroxybenzoyl acrylic acid and derivatives, which is applied in the field of 4-hydroxybenzoyl acrylic acid derivatives, can solve the problems of lack of treatment means and protection measures, and achieve good antibacterial effect, simple preparation method, and easy operation

Inactive Publication Date: 2012-12-12
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The world is facing a post-antibiotic era, when many common infections will be incurable and many people will die from common infections due to the lack of effective treatments and protective measures

Method used

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  • 4-hydroxybenzoylacrylic acid derivative, preparation method thereof and application
  • 4-hydroxybenzoylacrylic acid derivative, preparation method thereof and application
  • 4-hydroxybenzoylacrylic acid derivative, preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0027] The preparation of embodiment 14-methyl methoxybenzoyl acrylate

[0028] (a) Preparation of 4-methoxybenzoylacrylic acid

[0029] Add 10g of 4-hydroxybenzoylacrylic acid (52.04mmol) and 10.77g of potassium carbonate (78.06mmol) into 100mL of acetone, stir and react at 25°C for 0.5 hours, then add 8.86g of methyl iodide (62.44mmol) dropwise, After the addition, the reaction solution was heated to 56°C for reflux reaction for 4 hours; after the reaction was completed, the acetone was removed by rotary evaporation under reduced pressure, and the residual solution was poured into 100 mL of ice water to precipitate a white solid, which was dried in vacuo to obtain 10.19 g of a white powdery solid, which was collected The rate is 95%. The test results are as follows:

[0030] 1 H NMR (400MHz, DMSO-d 6 ) δppm: 3.81 (3H, s), 6.99 (1H, d, J = 15.2Hz), 7.09 (2H, m), 8.05 (2H, m), 8.21 (1H, d, J = 15.2Hz).

[0031] MS (ESI, m / z): 207.1 (M + +1, 100%).

[0032] (b) Preparati...

Embodiment 24

[0036] The preparation of embodiment 24-benzyloxybenzoyl ethyl acrylate

[0037] (a) Preparation of 4-benzyloxybenzoic acid

[0038] 10.68 g of benzyl bromide (62.44 mmol) was used instead of methyl iodide, and according to the method of step (a) of Example 1, 14.1 g of off-white powdery solid 4-benzyloxybenzoacrylic acid was obtained, with a yield of 96%. The test results are as follows:

[0039] MS (ESI, m / z): 283.3 (M + +1, 100%).

[0040] (b) Preparation of 4-benzyloxybenzoyl ethyl acrylate

[0041] Using 100mL of ethanol instead of methanol as a solvent, and using the above-prepared 10g of 4-benzyloxybenzoylacrylic acid (35.42mmol) as a raw material, according to the method of step (b) of Example 1, 9.89g of off-white powdery solid 4 was obtained. -Benzyloxybenzoyl ethyl acrylate, yield 90%.

[0042] The test results are as follows:

[0043] 1 H NMR (400MHz, DMSO-d 6 )δppm: 1.32 (3H, m), 4.19 (2H, m), 5.22 (2H, s), 6.58 (1H, d, J=15.2Hz), 7.10 (2H, m), 7.34-7.47 (...

Embodiment 34

[0045] The preparation of embodiment 34-cyclohexyloxybenzoyl ethyl acrylate

[0046] (a) Preparation of 4-cyclohexyloxybenzoic acid

[0047] Using 7.41g of chlorocyclohexane (62.44mmol) instead of methyl iodide, according to the method of step (a) of Example 1, 13.28g of off-white powdery solid 4-cyclohexyloxybenzoacrylic acid was obtained, with a yield of 93%. The test results are as follows:

[0048] MS (ESI, m / z): 275.3 (M + +1, 100%).

[0049] (b) Preparation of 4-cyclohexyloxybenzoyl ethyl acrylate

[0050] Using 100mL of ethanol instead of methanol as a solvent, and using the above-prepared 10g of 4-cyclohexyloxybenzoylacrylic acid (36.46mmol) as a raw material, according to the method of step (b) of Example 1, 9.04g of off-white powdery solids were obtained 4-Cyclohexyloxybenzoyl ethyl acrylate, yield 86%.

[0051] The test results are as follows:

[0052] 1 H NMR (400MHz, DMSO-d 6 )δppm: 1.43-1.95 (10H, m), 3.60 (1H, m), 3.82 (3H, s), 6.56 (1H, d, J=15.2Hz), 7....

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Abstract

The invention provides a 4-hydroxybenzoylacrylic acid derivative. The 4-hydroxybenzoylacrylic acid derivative is a compound which is represented as formula I, wherein R1 is C1-C8 alkyl, C1-C8 alkyl which is substituted by halogen or hydroxyl, C6-C8 aryl, C1-C9 alkanoyl or C6-C9 aroyl; and R2 is C1-C8 alkyl, C6-C8 aryl, C1-C8 alkylamino or C6-C8 arylamino. The 4-hydroxybenzoylacrylic acid derivative has inhibitory activity for mycobacterium tuberculosis protein kinase PknB can inhibit mycobacterium tuberculosis, multidrug resistant mycobacterium tuberculosis and several drug resistant Gram-positive bacterium such as methicillin-resistant staphylococcus aureus, methicillin-resistant staphylococcus epidermidis and vancomycin-resistant enterococci, no cross resistance exists in the 4-hydroxybenzoylacrylic acid derivative and existing antibiotics and the 4-hydroxybenzoylacrylic acid derivative has good antibacterial effect.

Description

technical field [0001] The invention relates to a 4-hydroxybenzoylacrylic acid derivative with antibacterial effect, its preparation method and its application. It belongs to the field of medicine. Background technique [0002] Tuberculosis is a chronic infectious disease caused by Mycobacterium tuberculosis that seriously endangers human health. For a long time, the main means for people to fight against tuberculosis is to use antibiotics for chemical treatment, which once effectively controlled the spread and spread of tuberculosis in the world. However, in recent years, due to the emergence of drug-resistant (MDR) and super-drug-resistant (XDR) Mycobacterium tuberculosis, tuberculosis, which has been effectively controlled, has made a comeback, and its morbidity and mortality have risen significantly. Malaria is also known as the three major killers of infectious diseases, and the World Health Organization stated in its report that tuberculosis has become the number one...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/736C07C67/08C07C69/73C07C235/34C07C231/02A61K31/235A61K31/222A61K31/216A61K31/165A61P31/04A61P31/06
Inventor 余利岩黄彬王玉成许乐幸游雪甫刘红宇张玉琴司书毅
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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