Ethoxy bridged thiazole coumarin compounds and preparation method and application thereof

A technology of ethoxy bridging and coumarin, applied in medical preparations containing active ingredients, organic chemistry, pharmaceutical formulations, etc., to achieve the effect of solving drug resistance

Active Publication Date: 2019-09-27
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its toxic side effects such as liver toxicity, it has not been widely used clinically. However, the coumarin ring is easy to mo

Method used

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  • Ethoxy bridged thiazole coumarin compounds and preparation method and application thereof
  • Ethoxy bridged thiazole coumarin compounds and preparation method and application thereof
  • Ethoxy bridged thiazole coumarin compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0061] Preparation of Intermediate III

[0062]

[0063] Add 2-acetylthiazole (15.0g, 0.12mol) into a 100mL round bottom flask, use glacial acetic acid (30mL) as solvent, bromine (21.5g, 0.135mol) is diluted with glacial acetic acid in the dropping funnel and slowly drop into Stir the reaction at 50°C in a round-bottomed flask, absorb the tail gas from a saturated sodium carbonate solution, and follow up with thin-layer chromatography until the end of the reaction. After cooling to room temperature, a light yellow solid was precipitated, filtered with suction, and the filter residue was washed twice with ether, dried and other post-treatments to obtain Intermediate III (18.0 g), with a yield of 73.2%.

experiment example 2

[0065] Preparation of Intermediate IV

[0066]

[0067] Add 7-hydroxycoumarin (720mg, 4.4mmol), potassium carbonate (670mg, 4.88mmol) and intermediate III (1.0g, 4.9mmol) into a 50mL round bottom flask, with acetonitrile (25mL) as solvent, 60°C The reaction was stirred under low pressure, followed by TLC until the end of the reaction, cooled to room temperature, separated by column chromatography, dried and other post-treatments to obtain intermediate IV (700 mg), yield 54.9%; white solid; melting point: 179-180 ° C, Among them, 7-hydroxycoumarin is obtained by Pechmann reaction with resorcinol as the starting material. 1 H NMR (600MHz, DMSO-d 6 )δ8.33(d, J=2.2Hz, 1H, thiazolyl-4-H), 8.24(d, J=2.4Hz, 1H, thiazolyl-5-H), 8.00(d, J=9.4Hz, 1H, coumarin-4-H), 7.65 (d, J = 8.6Hz, 1H, coumarin-5-H), 7.09 (s, 1H, coumarin-6-H), 7.04 (dd, J = 8.6, 1.9Hz, 1H , coumarin-8-H), 6.31 (d, J=9.5Hz, 1H, coumarin-3-H), 5.80 (s, 2H, OCH 2 )ppm.

experiment example 3

[0069] Preparation of Intermediate V

[0070]

[0071] 4-Methyl-7-hydroxycoumarin (880mg, 5.0mmol), potassium carbonate (691mg, 5.5mmol) and Intermediate III (1.1g, 5.5mmol) were added to a 50mL round bottom flask and dissolved in acetonitrile (25mL) As a solvent, stir the reaction at 60°C, follow up to the end of the reaction by thin-layer chromatography, cool to room temperature, and obtain intermediate V (800 mg) after separation by column chromatography and drying, with a yield of 53.2%; pink solid; melting point: 225-226 ° C, wherein 4-methyl-7-hydroxycoumarin is obtained by Pechmann reaction with resorcinol as the starting material. 1 H NMR (600MHz, DMSO-d 6 )δ8.32(d, J=3.0Hz, 1H, thiazolyl-4-H), 8.23(d, J=2.9Hz, 1H, thiazolyl-5-H), 7.69(d, J=8.6Hz, 1H, coumarin-5-H), 7.09–7.03 (m, 2H, coumarin-6, 8-H), 6.22 (s, 1H, coumarin-3-H), 5.80 (s, 2H, OCH 2 ),2.40(s,3H,CH 3 )ppm.

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Abstract

The invention relates to ethoxy bridged thiazole coumarin compounds and a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The general formula of the ethoxy bridged thiazole coumarin compounds is as shown in formulas I-II, and the formulas are shown in the description. The compounds have certain inhibitory activity against one or more of gram-positive bacteria, gram-negative bacteria and fungi, and can be used for preparing antibacterial and/or antifungal drugs, thereby having a chance to provide more safe and efficient diversified candidate drugs for clinical antimicrobial treatment, and being conducive to solving clinical treatment problems such as increasingly serious drug resistance, stubborn pathogenic microorganisms, emerging harmful microorganisms and the like. Raw materials for preparation are simple, and cheap and easy to obtain, the synthetic route is short, and the ethoxy bridged thiazole coumarin compounds are of great significance to infection resistance.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to ethoxy bridged thiazole coumarin compounds, a preparation method and application thereof. Background technique [0002] Natural and synthetic coumarins are a class of aromatic oxygen heterocyclic compounds based on benzoα-pyrone. Due to their large conjugated system and strong intramolecular electron transfer ability, this special rigid dense The ring structure is easy to interact with active molecules and active binding sites in organisms through various non-covalent interactions such as hydrogen bonds, hydrophobic interactions, π-π stacking, and electrostatic interactions, thus showing a broad spectrum. In recent years, especially in the field of medicinal chemistry, it has shown great development value and broad application prospects, making more and more research work devoted to the development of drugs with coumarin as the basic skeleton, such as in an...

Claims

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Application Information

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IPC IPC(8): C07D413/12A61K31/427A61P31/04A61P31/10
CPCC07D413/12A61P31/04A61P31/10Y02A50/30
Inventor 周成合胡春芳耿蓉霞
Owner SOUTHWEST UNIVERSITY
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