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Chalcone derivatives with drug-resistant bacteria resistance activity

A technology of chalcone derivatives and drug-resistant bacteria, applied in antibacterial drugs, organic chemistry, etc., can solve the severe problems of antibiotic treatment and achieve good antibacterial effect and good antibacterial effect

Inactive Publication Date: 2016-06-01
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 drug-resistant bacteria resistance activity
  • Chalcone derivatives with drug-resistant bacteria resistance activity
  • Chalcone derivatives with drug-resistant bacteria resistance activity

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 -Pyridine carboxaldehyde) (722ul, 7.58mmol) was added to a 100ml Erlenmeyer flask, 50ml of ethanol was added to ultrasound 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-neck bottle, the reaction continues at room temperature after the addition is completed, and the system is brown and clear at this time. 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 50 ml of ice water. A large amount of yellow solid was precipitated immediately. The filter cake was washed with water to neutrality and va...

Embodiment 2

[0043] Preparation of compound 5b

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

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

[0046] 1 HNMR(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=15.3,1.1 Hz, 1H), 7.66 (d, J = 8.7 Hz, 2H), 7.48-7.33 (m, 1H), 7.28 (dt, J = 8.5, 4.3 Hz, 1H), 4.16 (s, 2H).

[0047] 13 CNMR (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)CalcdforC 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-pyridinecarboxaldehyde, and compound 4 is chloroacetyl chloride. The preparation method is the same as in Example 1.

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

[0053] 1 HNMR (400MHz, DMSO) δ 10.72 (s, 1H), 8.81 (d, J = 1.9 Hz, 1H), 8.23-8.08 (m, 4H), 7.91 (d, J = 8.4 Hz, 1H), 7.80 ( d, J = 8.6 Hz, 2H), 7.69 (d, J = 15.4 Hz, 1H), 4.32 (d, J = 6.3 Hz, 2H).

[0054] 13 CNMR(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)CalcdforC 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 and until 1952, 75% of the Staphylococcus aureus strains isolated from clinical cases were resistant to penicillin. In recent years, with the emergence of Enterobacteriaceae bacteria resistant to carbapenem antibacterial drugs, 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 an en...

Claims

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Application Information

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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
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