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N-[(1-aryl-3-substituted phenyl-pyrazol-4-yl) methenyl]-2-hydroxyl benzoyl hydrazine compound or pharmaceutically acceptable salts and preparation method thereof

A kind of technology of hydroxybenzoic hydrazide and compound, applied in the field of N-[methine]-2-hydroxybenzoic hydrazide compounds

Inactive Publication Date: 2013-02-27
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Another example is WO2004033432A, which discloses a pyrazole compound for the prevention or treatment of antifungal diseases, but compared with ketoconazole, it has no obvious advantages in anti-Candida albicans

Method used

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  • N-[(1-aryl-3-substituted phenyl-pyrazol-4-yl) methenyl]-2-hydroxyl benzoyl hydrazine compound or pharmaceutically acceptable salts and preparation method thereof
  • N-[(1-aryl-3-substituted phenyl-pyrazol-4-yl) methenyl]-2-hydroxyl benzoyl hydrazine compound or pharmaceutically acceptable salts and preparation method thereof
  • N-[(1-aryl-3-substituted phenyl-pyrazol-4-yl) methenyl]-2-hydroxyl benzoyl hydrazine compound or pharmaceutically acceptable salts and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0059] Synthesis of N-{[1-(4-chlorophenyl)-3-phenyl-pyrazol-4-yl]methine}-2-hydroxybenzohydrazide

[0060] (1) Synthesis of p-chlorophenylhydrazine

[0061] In a 100ml three-necked flask equipped with a thermometer, add 3.8g (0.030mol) of p-chloroaniline, add an appropriate amount of absolute ethanol to dissolve it, add 8ml of concentrated HCl with a mass fraction of 36%, add 8ml of water, and stir for 0.5 h, forming a p-chloroaniline hydrochloride solution, cooling down to 0°C in an ice bath, weighing 2.2g (0.303mol) sodium nitrite and adding a small amount of distilled water to dissolve, adding p-chloroaniline hydrochloride solution under the liquid surface, until starch potassium iodide test paper micro Stop the dropwise addition when it is blue, stir for 0.5h, stop the reaction, and obtain a light yellow transparent diazonium solution.

[0062] In a 100ml three-necked flask equipped with a thermometer and a reflux condenser, add 9.45g (0.075mol) of sodium sulfite, add dis...

Embodiment 2

[0079] Synthesis of N-[(1,3-diphenyl-pyrazol-4-yl)methine]-2-hydroxybenzohydrazide

[0080] Using aniline as raw material, according to the method of Example 1, obtained phenylhydrazine (I-2): light yellow liquid, yield 93.8%; acetophenone phenylhydrazone (II-2): white powder, yield 93.1%, m.P.22-23°C; 1,3-diphenyl-4-formylpyrazole (III-2): white powder, yield 80%, m.P.116-117°C; N-[(1,3-diphenyl yl-pyrazol-4-yl)methine]-2-hydroxybenzohydrazide (IV-2), white solid, yield 81.2%, m.P.188-189°C.

[0081] The structure of IV2 is characterized as follows:

[0082] IR (cm -1 )ν:

[0083] 3411 (O-H), 3271 (N-H), 1641 (C=O), 1612 (drazoneC=N), 1537 (Pyrazole C=N), 1505 (C=C).

[0084] 1 H NMR (300MHz, DMSO) δ (ppm):

[0085] 11.79(s, 1H, OH), 9.96(s, 1H, NH), 9.02(s, 1H, Pyrazole-H), 8.59(s, 1H, CH=N), 8.03(d, J=7.8Hz, 2H , Ar-H), 7.87(d, J=7.2Hz, 1H, Ar-H), 7.76(d, J=6.6Hz, 2H, Ar-H), 7.56(t, J=7.5Hz, 5H, Ar-H) -H), 7.50-7.37 (m, 2H, Ar-H), 6.96 (t, J=7.5Hz, 2H Ar-H).

[008...

Embodiment 3

[0089] Synthesis of N-{[1-(3-chlorophenyl)-3-phenyl-pyrazol-4-yl]methine}-2-hydroxybenzohydrazide

[0090] Using m-chloroaniline as raw material, according to the method of Example 1, m-chlorophenylhydrazine (I-3): light yellow oil, yield 91.2%; acetophenone m-chlorophenylhydrazone (II-3): white powder , yield 91.2%, m.P.75-77°C; 1-(3-chlorophenyl)-3-phenyl-4-formylpyrazole (III-3): light yellow powder, yield 71.2%, m.P.121 -123°C; N-{1-(3-chlorophenyl)-3-phenyl-pyrazol-4-yl]methine}-2-hydroxybenzohydrazide (IV-3), pale yellow solid , yield 83.9%, m.P.184-186°C.

[0091] The structural characterization of IV-3 is as follows:

[0092] IR (cm -1 )ν:

[0093] 3392 (O-H), 3265 (N-H), 1646 (C=O), 1620 (drazoneC=N), 1548 (PyrazoleC=N), 1491 (C=C).

[0094] 1 H NMR (400MHz, DMSO) δ (ppm):

[0095] 11.79(s, 1H, OH), 9.99(s, 1H, NH), 9.13(s, 1H, Pyrazole-H), .59(s, 1H, CH=N), 8.16(s, 1H, Ar-H ), 8.03(d, J=9.2Hz, 1H, Ar-H), 7.87(d, J=8.8Hz, 1H, Ar-H), 7.77(d, J=6.8Hz, 2H, Ar-H),...

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Abstract

The invention provides an N-[(1-aryl-3-substituted phenyl-pyrazol-4-yl) methenyl]-2-hydroxyl benzoyl hydrazine compound in a formula (IV) or pharmaceutically acceptable salts and a preparation method thereof. The preparation method comprises the following steps of: diazotizing and reducing arylamine as a raw material, condensing with a product obtained from diazotizing and reducing for Vilsmeier-Haak reaction to obtain 1-aryl-3-phenyl-4-formoxyl pyrazol; and then reacting the 1-aryl-3-phenyl-4-formoxyl pyrazol with salicylyl hydrazine to obtain the N-[(1-aryl-3-substituted phenyl-pyrazol-4-yl) methenyl]-2-hydroxyl benzoyl hydrazine compound shown as the following general formula, wherein each substituent in the formula is defined in the specification. The compound has a good application prospect at the aspect of resisting fungi and Gram negative bacteria.

Description

technical field [0001] The present invention relates to a kind of N-[(1-aryl-3-substituted phenyl-pyrazol-4-yl)methine]-2-hydroxybenzoic hydrazide compound or its pharmaceutically acceptable salt and its preparation Methods and their application in antimicrobial aspects. Background technique [0002] In recent years, the number of immunocompromised patients caused by cancer chemotherapy, organ transplantation, and AIDS has surged, resulting in an alarming increase in the incidence of microbial infections. AIDS (AIDS) is the world's largest epidemic disease, causing 20 million deaths every year. In developing countries, there are only 300-500 million new cases of malaria each year, and 1-3 million deaths. Infectious diseases occur frequently. In the past 30 years, nearly 40 new infectious diseases and pathogens have been discovered in the world. However, the current clinically used antimicrobial drugs generally have problems such as large side effects, narrow antibacterial ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/12A61K31/415A61P31/10A61P31/04A61P31/12
Inventor 卢俊瑞邹敏
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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