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Preparation method of triazolobenzothiazole derivative

A technology of benzothiazole and derivatives is applied in the field of preparation of antibacterial drugs, and achieves the effects of easy large-scale production, easy operation and strong antibacterial activity

Active Publication Date: 2020-08-21
TANGSHAN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, people have found that more and more bacteria have developed serious resistance to existing antibacterial drugs in the clinical treatment of anti-infection, and even "super bacteria" that are resistant to almost all antibacterial drugs have appeared. To deal with the increasingly serious problem of bacterial resistance, it is urgent to develop new and more effective antibacterial drugs

Method used

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  • Preparation method of triazolobenzothiazole derivative
  • Preparation method of triazolobenzothiazole derivative
  • Preparation method of triazolobenzothiazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Add 3 mL of 85% hydrazine hydrate (40 mmol) into a 100 mL flask, and then add 2 mL of concentrated hydrochloric acid (20 mmol) dropwise while stirring in an ice-water bath. After the dropwise addition, 2-aminobenzothiazole derivative (10 mmol) and 15 mL ethylene glycol were added, and the reaction was carried out under reflux for 10 hours. After the reaction was completed, the solid was precipitated after cooling, filtered, washed with water, and recrystallized with ethanol to obtain compound 2 ( white crystals). Its chemical reaction process is:

[0030]

[0031] where R 1 It is hydrogen, halogen, alkyl, preferably one of hydrogen, chlorine, bromine, fluorine and methyl;

[0032] (2) Take a 100 mL dry flask, add compound 2 (2 mmol), p-chloromethylbenzoyl chloride 3 (2.1 mmol) and phosphorus oxychloride (11 mL), heat and reflux under stirring for 8 hours, after the reaction , cooled, and then the reaction solution was poured into ice water to precipitate solid...

Embodiment 2

[0045] When the raw material is 2-aminobenzothiazole, ie R 1 is H, and the arylhydrazide is 2-chlorobenzohydrazide, namely R 2 When it is 2-chloro, obtain the final product compound Ib according to the preparation method of Example 1, named after: 3-(4-(((5-(2-chlorophenyl)-1,3,4-thiadiazole- 2-yl) thio) methyl) phenyl) benzo [4,5] thiazole [2,3-c] [1,2,4] triazole; compound Ib structure is as follows:

[0046]

[0047] After testing, the compound b: light yellow solid, yield 55.2 %, m.p. 214.2~216.3 ℃; 1 H NMR (DMSO- d 6 , 600 MHz) δ: 8.48 (d, J =7.8 Hz, 2H, ArH), 8.07 (d, J = 8.4 Hz, 2H,ArH), 7.94 (d, J =7.2 Hz, 1H, ArH), 7.56 (m, 2H, ArH), 7.52 (m,2H, ArH), 7.44(m, 1H, ArH), 7.36 (d, J =7.2 Hz, 2H, ArH), 4.40 (s, 2H, CH 2 ); 13 C NMR (DMSO- d 6 , 150 mHz) Δ: 38.3, 121.6, 121.7, 123.5, 124.3, 125.9, 128.3, 128.6, 129.5, 130.9, 132.9, 137.3, 150.4, 164.2, 174.2; ms (ESI); ms (ESI)) m / z: 491.1 ([M-H] + ).

Embodiment 3

[0049] When the raw material is 2-aminobenzothiazole, ie R 1 is H, and the arylhydrazide is 2,4-dichlorobenzohydrazide, ie R 2 When it is 2,4-dichloro, the final product compound Ic is obtained according to the preparation method of Example 1, named as: 3-(4-(((5-(2,4-dichlorophenyl)-1,3, 4-thiadiazol-2-yl)thio)methyl)phenyl)benzo[4,5]thiazolo[2,3-c][1,2,4]triazole; Compound Ic has the following structure:

[0050]

[0051] After testing, the compound c: light yellow solid, yield 53.4 %, m.p. 225.0~227.3 ℃; 1 H NMR (DMSO- d 6 , 600 MHz) δ: 8.50 (d, J = 7.2 Hz, 2H, ArH), 8.01 (d, J = 7.8 Hz, 2H,ArH), 7.95 (d, J = 7.2 Hz, 1H, ArH), 7.58(m, 1H, ArH), 7.50 (m,2H, ArH), 7.45(m, 1H, ArH), 7.41 (d, J = 7.2 Hz, 2H, ArH), 4.43 (s, 2H, CH 2 ); 13 C NMR (DMSO- d 6 , 150 mHz) Δ: 38.1, 120.7, 121.3, 122.5, 124.7, 125.9, 128.1, 128.6,129.2, 129.5, 133.3, 137.2, 137.9, 162.2, 163.2, 172.2; ms (eSI) m / m / m / ESI) m / m / m / ESI) m / m / m / ms (esi) m / m / m / m / ESI) m / m / m / ms (eS...

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Abstract

The invention discloses a preparation method of a triazolobenzothiazole derivative. The preparation method comprises the following steps: with a 2-aminobenzothiazole derivative and an aromatic hydrazide compound as initial raw materials, carrying out a reflux reaction on the 2-aminobenzothiazole derivative 1 and hydrazine hydrate in an ethylene glycol solvent under the action of hydrochloric acidto obtain a compound 2; further reacting the compound 2 with p-chloromethylbenzoyl chloride under the action of phosphorus oxychloride to obtain a compound 4; dissolving aromatic hydrazide and a proper amount of KOH in ethanol, reacting the formed solution with CS2 at normal temperature to obtain a compound 6; subjecting the compound 6 to a reaction under the action of concentrated sulfuric acid to obtain a compound 7; and reacting the compound 4 and the compound 7 in an acetonitrile solvent under the catalytic action of potassium carbonate to obtain a target product. The method is simple in process, easy to operate and easy for large-scale production; and experiments prove that the prepared compound I has high bacteriostatic activity and can be widely applied to pharmaceutical bacteriostatic preparations.

Description

[0001] This application is a divisional application of an invention patent application with application number 201810054296.3 and titled "A Triazolobenzothiazole Derivative and Its Preparation Method and Application". technical field [0002] The invention relates to a preparation method of antibacterial drugs, in particular to a preparation method and application of a triazolobenzothiazole derivative. Background technique [0003] At present, people have found that more and more bacteria have developed serious resistance to existing antibacterial drugs in the clinical treatment of anti-infection, and even "super bacteria" that are resistant to almost all antibacterial drugs have appeared. To deal with the increasingly serious problem of bacterial drug resistance, it is urgent to develop new and more effective antibacterial drugs. [0004] Nitrogen-containing heterocyclic compounds have a wide range of biological activities, and many drug structures contain such structures. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04A61P31/04
CPCC07D513/04A61P31/04Y02A50/30
Inventor 李艾李海花
Owner TANGSHAN COLLEGE