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Application of Schiff base compounds in the preparation of drugs for inhibiting ndm-1 activity

A compound, Schiff base technology, applied in the application field of Schiff base compounds, can solve problems such as high in vitro sensitivity, and achieve the effects of improving curative effect, eliminating hydrolysis, and treating drug-resistant bacterial infections

Inactive Publication Date: 2016-11-16
TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existence of NDM-1 is the molecular basis that causes NDM-1 super bacteria to be resistant to almost all β-lactam antibacterial drugs. At the same time, because bacteria have other drug resistance mechanisms, they are also resistant to aminoglycosides and quinolones. High in vitro sensitivity only to colistin and tigecycline

Method used

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  • Application of Schiff base compounds in the preparation of drugs for inhibiting ndm-1 activity
  • Application of Schiff base compounds in the preparation of drugs for inhibiting ndm-1 activity
  • Application of Schiff base compounds in the preparation of drugs for inhibiting ndm-1 activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0039] The preparation of embodiment 12-[(5-methyl-3-isoxazolyl) imino] methylphenol

[0040]

[0041] Add salicylaldehyde (610 mg, 5 mmol) and 3-amino-5-methylisoxazole (490 mg, 5 mmol) into a 100 ml reaction flask, dissolve with 50 ml of absolute ethanol, and reflux at 80° C. for 3 hours. After cooling the solution, the solvent was distilled off under reduced pressure, recrystallized from absolute ethanol, and dried in vacuo to obtain 920 mg of the title compound with a yield of 80%. The compound is a yellow needle-like crystal, and its identification data are as follows: M.p.: 147~148°C; ESI-MS: m / z 203.22 ([M+H + ]); 1 HNMR (600MHz, CDCl 3 , δppm): 12.46(s, 1H), 8.92(s, 1H), 7.48(m, 2H), 7.29(d, J=7.8Hz, 1H), 7.06(m, 1H), 6.14(s, 1H) , 2.49(s, 3H).

Embodiment 22

[0042] Preparation of Example 22-{[(2-hydroxyphenyl)imino]methyl}phenol

[0043]

[0044] Add salicylaldehyde (610 mg, 5 mmol) and 2-aminophenol (545 mg, 5 mmol) into a 100 ml reaction flask, dissolve with 50 ml of absolute ethanol, and reflux at 80° C. for 3 hours. After cooling the solution, the solvent was distilled off under reduced pressure, recrystallized from absolute ethanol, and dried in vacuo to obtain 860 mg of the title compound with a yield of 80%. The compound is a red solid, and its identification data are as follows: M.p.: 203-205°C; ESI-MS: m / z 214.24 ([M+H + ]); 1 HNMR (400MHz, DMSO-d 6 , δppm): 13.78(s, 1H), 9.72(s, 1H), 8.97(s, 1H), 7.60(m, 1H), 7.40(m, 2H), 7.35(m, 1H), 6.98(m, 3H), 6.96(s, 1H).

Embodiment 3

[0045] The preparation of embodiment 32-(N-benzylidene amino) phenol

[0046]

[0047] Benzaldehyde (530mg, 5mmol) and 2-aminophenol (545mg, 5mmol) were added into a 100ml reaction flask, dissolved in 50ml of absolute ethanol, and refluxed at 80°C for 3 hours. After cooling the solution, the solvent was distilled off under reduced pressure, recrystallized from absolute ethanol, and dried in vacuo to obtain 850 mg of the title compound with a yield of 86%. The compound is a gray blocky solid, and its identification data are as follows: M.p.: 91-93°C; ESI-MS: m / z 198.24 ([M+H + ]); 1 HNMR (400MHz, CDCl 3 , δppm): 8.74(s, 1H), 7.94(s, 2H), 8.13(m, 3H), 7.34(m, 1H), 7.26(m, 1H), 7.06(m, 1H), 6.97(m, 1H).

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Abstract

The invention provides application of a Schiff base compound in preparation of a medicine used for inhibiting activity of drug-resistant bacteria, especially in preparation of a medicine used for inhibiting activity of drug-resistant bacteria generating NDM-1. The Schiff base compound has a structural general formula (I) as described in the specification; in the general formula (I), an A ring is an aromatic ring group or a hetero-aromatic ring group, a B ring is an aromatic ring group or a hetero-aromatic ring group, R1 is selected from the group consisting of hydrogen, a hydroxyl group, a halogen, a C1-C4 alkyl group, a C1-C4 halogenated alkyl group, a C1-C4 alkoxy group and a nitro group, R2 is selected from the group consisting of hydrogen, a hydroxyl group, a halogen, a C1-C4 alkyl group, a C1-C4 halogenated alkyl group, a nitro group, a benzoyl group, a C1-C4 alkylamido group and an aryloxy group, and X represents inexistence or a methylene group or an ethylidene group. The Schiff base compound has the effect of inhibiting activity of NDM-1.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to the application of Schiff base compounds. Background technique [0002] Antibiotics are a class of chemical substances produced by certain microorganisms in the course of life, which can inhibit or kill some other pathogenic microorganisms. It is also the main weapon for humans to resist bacterial infections. However, in August 2010, the famous medical journal "The Lancet" reported a case of resistance to all β-lactam antibiotics, insensitive to ciprofloxacin, and only sensitive to colistin. It carries a new type of metallo-beta-lactamase encoded by Klebsiella pneumoniae (Klebsiella pneumoniae), and the enzyme is named New Delhi metallo-beta-lactamase (NDM-1) according to the possible infection place of the patient (New Delhi, India). , New Delhi metallo-β-lactamase-1). This enzyme can exist in the DNA of Escherichia coli to make it widely resistant to drugs, and it is diffic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/42A61K31/137A61K31/167A61P31/04
CPCY02A50/30
Inventor 饶子和杨诚娄智勇肖燕燕夏强刘伟谢楠楠
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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