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A kind of triazole Schiff base compound and its preparation method and application

A technology for triazole Schiff bases and compounds is applied in the field of triazole Schiff base compounds and their preparation, which can solve the problems of increasing bacterial infection rate and morbidity rate, and achieve easy implementation, good application prospect, broad-spectrum antibacterial active effect

Active Publication Date: 2021-03-05
TIANJIN RUILING CHEM CO LTD
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Problems solved by technology

[0003] However, with the rapid increase of bacterial resistance caused by the abuse of antibiotics, the infection rate and pathogenicity rate of bacteria are rapidly increasing.

Method used

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  • A kind of triazole Schiff base compound and its preparation method and application
  • A kind of triazole Schiff base compound and its preparation method and application
  • A kind of triazole Schiff base compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] 5-(4-(2-Hydroxy-benzyl)amino-5-methyl-4H-1,2,4-triazole-3-sulfanyl)-1,3,4-oxadiazole-2 -The preparation of mercaptan, step is as follows:

[0048] 1) Add 20mL of methanol into a 50mL three-necked flask, and add 2.16g (10mmol) of 3-methyl-4-amino-5-ethoxycarbonylmethylthio-1,2,4-triazole under stirring to make it Dissolve completely, slowly add 1.2mL (30mmol) of hydrazine hydrate dropwise, follow the reaction with thin-layer chromatography (TLC), the developer is a mixture of dichloromethane and methanol with a volume ratio of 6:1, after the reaction is completed, spin off part of the solvent, and crystallized to obtain 1.6g of 3-methyl-4-amino-5-acetic acid hydrazide with a yield of 78.8%. m.p.146-148℃. 1 H NMR (400MHz, DMSO-d 6 ),9.30(s,1H,NH),5.88(s,2H,NH 2 ),4.31(s,2H,NH 2 ),3.76(s,2H,CH 2 ),2.28(s,3H,CH 3 ). 13 C NMR (100MHz, DMSO-d 6 ),167.20,153.80,151.01,33.87,10.24.ESI-MS,m / z:203.0720[M+H] + .

[0049] 2) Add 15mL of ethanol to a 100mL three-necked fl...

Embodiment 2

[0053] 5-(4-(2-Hydroxy-5-bromo-benzyl)amino-5-methyl-4H-1,2,4-triazole-3-sulfanyl)-1,3,4-oxa The preparation steps of oxadiazole-2-thiol are as follows:

[0054] 1) The preparation method of 3-methyl-4-amino-5-acetic acid hydrazide is the same as in Example 1.

[0055] 2) Preparation method and implementation of 5-(4-amino-5-phenyl-4H-1,2,4-triazole-3-sulfanyl)-1,3,4-oxadiazole-2-thiol Example 1 is the same.

[0056] 3) Add 20mL of ethanol to a 50mL round bottom flask, slowly add 2.44g (10mmol) of 5-(4-amino-5-phenyl-4H-1,2,4-triazole-3-sulfanyl) -1,3,4-Oxadiazole-2-thiol was stirred and dissolved, and then 2.21g (1.1mmol) of 5-bromosalicylaldehyde was added, and the pH was adjusted to 5-6 with dilute hydrochloric acid, and the reaction was stirred at 78°C. Thin-layer chromatography (TLC), the developer is a mixture of dichloromethane and methanol with a volume ratio of 10:1. After the raw material point disappears, the reaction solution is concentrated and separated by sil...

Embodiment 3

[0059] 5-(4-(2-Hydroxy-5-chloro-benzyl)amino-5-methyl-4H-1,2,4-triazole-3-sulfanyl)-1,3,4-oxa The preparation steps of oxadiazole-2-thiol are as follows:

[0060] 1) The preparation method of 3-methyl-4-amino-5-acetic acid hydrazide is the same as in Example 1.

[0061] 2) Preparation method and implementation of 5-(4-amino-5-phenyl-4H-1,2,4-triazole-3-sulfanyl)-1,3,4-oxadiazole-2-thiol Example 1 is the same.

[0062] 3) Add 20mL of ethanol to a 50mL round bottom flask, slowly add 2.44g (10mmol) of 5-(4-amino-5-phenyl-4H-1,2,4-triazole-3-sulfanyl) -1,3,4-Oxadiazole-2-thiol was stirred and dissolved, then 1.71g (1.1mmol) 5-chlorosalicylaldehyde was added, the pH was adjusted to 5-6 with dilute hydrochloric acid, the reaction was stirred at 78°C, and Thin-layer chromatography (TLC), the developer is a mixture of dichloromethane and methanol with a volume ratio of 10:1. After the raw material point disappears, the reaction solution is concentrated and separated by silica gel c...

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Abstract

The invention provides a triazole Schiff base compound and a preparation method and application thereof. The compound is a 1,2,4-triazole Schiff base compound modified by 1,3,4-oxadiazole. Two or moreheterocyclic active centers are simultaneously introduced into a drug molecule to significantly improve the biological activity. According to the principle of biological activity superposition, an ''o-hydroxyphenyl'' molecular fragment is rationally assembled with ''1,2,4-triazole'' and the ''1,3,4-oxadiazole''. The 1,2,4-triazole Schiff base compound modified by the 1,3,4-oxadiazole is designedand synthesized. The 1,2,4-triazole Schiff base compound modified by the 1,3,4-oxadiazole has good inhibitory activity against gram-negative bacteria, gram-positive bacteria and fungi, and the like, exhibits broad-spectrum antibacterial activity, has great development potential, and has good application prospects; and the preparation method is simple and easy to implement. The yield can reach 40-60%, and the method is suitable for large-scale industrial production needs.

Description

technical field [0001] The invention relates to the field of chemical medicines, in particular to a triazole Schiff base compound and its preparation method and application Background technique [0002] It has been found that 1,2,4-triazole compounds have antibacterial, anticancer, antiviral, anti-inflammatory, anticonvulsant and other activities, so they are favored by people (1, El S H.El A, El S H El T, Mohy E D A El F, et al. Eur. J. Med. Chem. 2013, 66, 106-113; 2. E, Karaali N, Y 1 lmaz F, etal.Arch.Pharm.Chem.Life Sci.2013,346,556-561), meanwhile, 1,3,4-oxadiazoles have excellent biological activities such as antibacterial and anticancer (1, Kumar, B P N ,Mohana K N, Mallesha L, etal.Int.J.Med.Chem.2013, 2013, 1-6; 2. Muhammad N A, Khawaja A Y, Shahid H, etal.J.Mol.Struct. 59). [0003] However, with the rapid increase of bacterial resistance caused by the abuse of antibiotics, the infection rate and pathogenicity rate of bacteria are rapidly increasing. Therefo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12C07D413/12A61P31/04A61P31/10
CPCC07D249/12C07D413/12
Inventor 卢俊瑞马瑶卢博为谢志强
Owner TIANJIN RUILING CHEM CO LTD
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