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Chalcone derivatives with activity against drug-resistant bacteria

A technology of chalcone derivatives and drug-resistant bacteria, applied in antibacterial drugs, organic chemistry and other directions, can solve problems such as severe antibiotic treatment situation, and achieve good bacteriostatic effect and good bacteriostatic effect.

Inactive Publication Date: 2017-12-26
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the situation of existing antibiotics for the treatment of MRSA is grim.

Method used

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  • Chalcone derivatives with activity against drug-resistant bacteria
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  • Chalcone derivatives with activity against drug-resistant bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Preparation of compound 5a

[0036] Take sodium hydroxide (370mg, 9.25mmol) in a 250ml single-necked round bottom flask, add 50ml of water and dissolve under magnetic stirring at room temperature; then compound 1 (p-aminoacetophenone) (1.00g, 7.40mmol) and compound 2 (2 -Pyridinecarbaldehyde) (722ul, 7.58mmol) was added in a 100ml Erlenmeyer flask, 50ml of ethanol was added to ultrasonically until the system was basically clear, and then the clear solution was added dropwise (1d / s) to the above-mentioned stirred sodium hydroxide solution In the single-necked bottle, after the dropwise addition, the reaction was continued at room temperature, and the system was brownish yellow and clear. After about 6h, TLC detection (PE:EA=1:1) showed that the reaction was complete. The reaction was stopped, and the reaction system was poured into about 50ml of ice water, and a large amount of yellow solids were precipitated immediately, filtered with suction, washed with water until n...

Embodiment 2

[0043] Preparation of compound 5b

[0044] Compound 1 is p-aminoacetophenone, compound 2 is 3-fluoro-2-pyridinecarbaldehyde, and compound 4 is chloroacetyl chloride. The preparation method is the same as in Example 1.

[0045] The product is a pale yellow solid with a yield of 98.8%, m.p.: 157-158°C.

[0046] 1 H NMR (400MHz, CDCl3) δ8.43 (d, J = 4.4Hz, 1H), 8.39 (s, 1H), 8.10 (dd, J = 24.8, 12.0Hz, 3H), 7.98 (dd, J = 15.3, 1.1Hz, 1H), 7.66(d, J=8.7Hz, 2H), 7.48–7.33(m, 1H), 7.28(dt, J=8.5, 4.3Hz, 1H), 4.16(s, 2H).

[0047] 13 C NMR(101MHz,CDCl3)δ187.55,163.02,144.75,144.70,140.02,133.67,133.28,129.25,125.45,125.41,124.95,124.90,123.00,122.81,118.36,76.33,76.21,76.01,75.69,41.87,-0.00, -1.03.

[0048] HR-MS (ESI) Calcd for C 16 h 13 ClFN 2 o 2 [M+H]+:319.0650,found:319.0648.

Embodiment 3

[0050] Preparation of compound 5c

[0051] Compound 1 is p-aminoacetophenone, compound 2 is 5-bromo-2-pyridinecarbaldehyde, and compound 4 is chloroacetyl chloride. The preparation method is the same as in Example 1.

[0052] The product is a pale yellow solid with a yield of 85.3%, m.p.: 226-227°C.

[0053] 1 H NMR (400MHz, DMSO) δ10.72(s, 1H), 8.81(d, J=1.9Hz, 1H), 8.23–8.08(m, 4H), 7.91(d, J=8.4Hz, 1H), 7.80 (d, J=8.6Hz, 2H), 7.69(d, J=15.4Hz, 1H), 4.32(d, J=6.3Hz, 2H).

[0054] 13 C NMR(101MHz,DMSO)δ187.63,165.24,151.71,150.73,143.11,141.26,139.75,132.41,130.02,126.29,125.69,121.21,118.86,43.60,40.13,39.92,39.71,39.51,39.30,39.09,38.88.

[0055] HR-MS (ESI) Calcd for C 16 h 13 BrClN 2 o 2 [M+H] + :378.9849,found:378.9850.

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Abstract

The invention belongs to the field of pharmaceutical chemistry, and discloses novel chalcone derivatives with drug-resistant bacteria resistance activity and a synthesis method thereof. The two reaction steps are performed to simply and quickly obtain the target products. The structure of the compounds is disclosed in the specification. The in-vitro antimicrobial activity experiment proves that the compounds have favorable antibacterial activity for methicillin-resistant Staphylococcus aureus (MRSA). The compounds are hopeful to be used as a novel candidate drug for resisting Gram-positive bacteria.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and discloses a novel chalcone derivative with anti-drug-resistant bacteria activity and a synthesis method thereof. Background technique [0002] In the 1940s, when penicillin was widely used in clinical treatment of severe staphylococcal infections, antimicrobial resistance became a serious challenge for clinicians. In 1947, from the first case of Staphylococcus aureus resistant to penicillin was reported until 1952, 75% of Staphylococcus aureus strains isolated from clinical cases showed resistance to penicillin. In recent years, with the emergence of Enterobacteriaceae bacteria resistant to carbapenem antibiotics, it indicates that antibacterial drugs have entered the post-antibiotic era. At the same time, the use of antibacterial drugs in hospitals, communities and agricultural production in high-income countries is increasing, and drug-resistant strains emerge in endlessly, for...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/50C07D213/61A61P31/04
CPCC07D213/50C07D213/61
Inventor 张恩秦上尚徐帅民王铭铭赵娣白鹏燕周萌萌王平王上王亚娜崔得运化永刚刘宏民
Owner ZHENGZHOU UNIV