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Application of sulfonamide compounds in inhibiting NDM-1 activity

A technology of sulfonamides and compounds, applied in the field of medicinal chemistry, can solve problems such as high in vitro sensitivity

Inactive Publication Date: 2013-07-10
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 sulfonamide compounds in inhibiting NDM-1 activity
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  • Application of sulfonamide compounds in inhibiting NDM-1 activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0055] The preparation of embodiment 14-iodo-N-(3-methoxyphenyl) benzenesulfonamide

[0056]

[0057] Select a 50ml round-bottomed flask as the reaction vessel, and at 0°C, dissolve p-iodobenzenesulfonyl chloride (302mg, 1mmol) in 10ml of ethanol, drop the solution into m-methoxyaniline (123mg, 1mmol), and then add Sodium bicarbonate (170mg, 2mmol), it is moved to room temperature, electromagnetic stirring, after TLC detects that reaction is complete, stops reaction, and 10ml water is joined in the solution after reaction, and white solid appears, and it is filtered out, to The obtained white solid was vacuum-dried to obtain 320 mg of the title compound with a yield of 82%. The identification data of this compound are as follows: ESI-MS: m / z 390.20 ([M+H + ]); 1 HNMR (400MHz, CDCl 3 , δppm): 7.82(dd, J=2.0Hz, 2.8Hz, 2H), 7.49(dd, J=2.0, 2.8Hz, 2H), 7.16(t, J=8.4Hz, 1H), 6.71(m, 2H ), 6.61 (d, J=1.2Hz, 1H), 6.51 (s, 1H), 3.78 (s, 3H).

Embodiment 24

[0058] The preparation of embodiment 24-methyl-N-phenylbenzenesulfonamide

[0059]

[0060] Replace the p-iodobenzenesulfonyl chloride in Example 1 with p-toluenesulfonyl chloride, and replace the m-methoxyaniline in Example 1 with aniline as a starting material, and use steps similar to Example 1 to prepare the compound , the yield was 76%. This compound is a white solid, and its identification data are as follows: ESI-MS: m / z 248.21 ([M+H + ]); 1 HNMR (400MHz, DMSO-d 6 , δppm): 10.19(s, 1H), 7.63(d, J=8.4Hz, 2H), 7.33(d, J=4.0Hz, 2H), 7.29(d, J=7.8Hz, 1H), 7.06(m , J=7.0Hz, 1H), 6.14(s, 1H), 2.49(s, 3H).

Embodiment 34

[0061] The preparation of embodiment 34-methyl-N-naphthylbenzenesulfonamide

[0062]

[0063] Replace the p-iodobenzenesulfonyl chloride in Example 1 with p-toluenesulfonyl chloride, and replace the m-methoxyaniline in Example 1 with 1-naphthylamine as a starting material, using steps similar to Example 1 , the compound was prepared with a yield of 72%. The compound is a white solid, and its identification data are as follows: ESI-MS: m / z 298.21 ([M+H + ]); 1 HNMR (400MHz, DMSO-d 6 , δppm): 10.16(s, 1H), 8.04(d, J=8.4Hz, 1H), 7.88(d, J=8.4Hz, 1H), 7.77(d, J=8.4Hz, 1H), 7.58(d , J=8.0Hz, 2H), 7.38(m, 3H), 7.30(d, J=8.0Hz, 2H), 7.14(dd, J=0.8, 7.6Hz, 1H), 2.33(s, 1H).

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Abstract

The invention provides an application of sulfonamide compounds in preparing medicines inhibiting medicine resistant bacteria activities, and especially relates to the application of sulfonamide compounds in preparing medicines inhibiting the activities of NDM-1-producing medicine resistant bacteria. The sulfonamide compounds have a general structural formula (I), wherein A ring represents C5-C10 aryl ring or a 5-10-element heteroaryl ring; R1 is selected from hydrogen, hydroxyl, halogen, C1-C6 alkyl, and C1-C4 alkoxy or nitro; R2 is selected from C1-C6 alkyl, C3-C6 cycloalkyl, C5-C10 aryl group, or a C5-C10 aryl-C1-C4 alkyl group. The aralkyl group is not substituted, or is substituted by any one or more groups selected from the following: halogen, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkanoyl, and C1-C4 alkanoyloxy or nitro. The compounds have the effect for inhibiting NDM-1 activity.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to the use of sulfonamide 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, and the enzyme is named New Delhi metallo-beta-lactamase (NDM-1) according to the place where the patient may be infected (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 difficult for people to be cured or ev...

Claims

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Application Information

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IPC IPC(8): A61K31/18A61K31/36A61P31/04
CPCY02A50/30
Inventor 饶子和杨诚娄智勇肖燕燕王静王泰一刘伟夏强
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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