A kind of quinolinothiopyran derivative with antibacterial activity and its synthesis method and application

The technology of a thiopyran derivative and a synthesis method is applied in the synthesis of heterocyclic compounds and the application field thereof, can solve the problems of complicated steps, no research on the antibacterial property of the compound, etc., and achieves cheap and easy availability of solvents, flexible reaction time, and application scope. wide effect

Active Publication Date: 2018-08-07
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] In addition, there are some other methods, but the steps are more cumbersome than the above three, so I will not list them here.
Although these methods synthesized a series of quinothiopyran derivatives, the antibacterial properties of these compounds were not studied

Method used

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  • A kind of quinolinothiopyran derivative with antibacterial activity and its synthesis method and application
  • A kind of quinolinothiopyran derivative with antibacterial activity and its synthesis method and application
  • A kind of quinolinothiopyran derivative with antibacterial activity and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] At 25°C, add 2-mercapto-quinoline-3-carbaldehyde 1a (38mg, 0.2mmol), DBU (7.0mg, 0.04mmol), and 2ml of acetone into a 5ml reaction tube in turn, followed by injection of 1-chloro Acrylonitrile (26mg, 0.3mmol), stirred for 10 minutes. The solvent was then removed under reduced pressure, and column chromatography was carried out using a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 12:1) as the eluent to obtain quinolinethiopyran derivative 2a (48mg , yield 88%). The reaction equation is as follows:

[0051]

[0052] The structure of the quinolinothiopyran derivative 2a obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR(600MHz,DMSO)δ8.43(s,1H),8.00(d,J=8.1Hz,1H),7.84(d,J=8.4Hz,1H),7.77–7.73(m,1H),7.64 (d, J=6.5Hz, 1H), 7.54(t, J=7.4Hz, 1H), 5.25(d, J=6.4Hz, 1H), 4.15(d, J=13.2Hz, 1H), 4.05(d ,J=13.2Hz,1H). 13 C NMR (151MHz, DMSO) δ155.1, 147.4, 137.5, ...

Embodiment 2

[0054]At 25°C, add 2-mercapto-quinoline-3-carbaldehyde 1b (41mg, 0.2mmol), DBU (7.0mg, 0.04mmol), and 2ml of acetone into a 5ml reaction tube in turn, followed by injection of 1-chloro Acrylonitrile (26mg, 0.3mmol), stirred for 10 minutes. The solvent is removed under reduced pressure subsequently, and the eluent is carried out column chromatography with the mixed solution of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate is 12:1) to obtain the quinolinothiopyran derivative of structural formula such as 2b Compound 2b (52 mg, yield 90%). The reaction equation is as follows:

[0055]

[0056] The structure of the quinolinothiopyran derivative 2b obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600MHz, DMSO) δ8.30 (d, J = 30.4Hz, 1H), 7.74 (t, J = 6.6Hz, 2H), 7.55 (ddd, J = 113.8, 63.8, 6.7Hz, 2H), 5.32 (dd, J=97.8,6.6Hz,1H),4.16(dd,J=45.5,13.2Hz,1H),3.99(dd,J=57.8,13.1Hz,1...

Embodiment 3

[0058] At 25°C, add 2-mercapto-quinoline-3-carbaldehyde 1c (41mg, 0.2mmol), DBU (7.0mg, 0.04mmol), and 2ml of acetone into a 5ml reaction tube in turn, followed by injection of 1-chloro Acrylonitrile (26mg, 0.3mmol), stirred for 10 minutes. Subsequently, the solvent was removed under reduced pressure, and column chromatography was carried out using a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 12:1) as the eluent to obtain quinolinethiopyran derivative 2c (51mg , yield 88%). The reaction equation is as follows:

[0059]

[0060] The structure of the quinolinothiopyran derivative 2c obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, Yellow soil (51 mg, 88% yield), m.p.203-205 ° C. 1 H NMR (600MHz, DMSO) δ8.33 (d, J = 30.1Hz, 1H), 7.82–7.72 (m, 2H), 7.68–7.37 (m, 2H), 5.35 (d, J = 98.6Hz, 1H) ,4.19(dd,J=46.6,13.2Hz,1H),4.03(dd,J=57.9,13.1Hz,1H),2.50(s,3H). 13 C NMR ...

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Abstract

The invention discloses a benzothiazepine derivative with antibacterial activity and a synthetic method and application thereof; the structural formula (I) of benzothiazepine derivative with antibacterial activity is shown as in formula (I) shown the description, wherein R is selected from a group of hydrogen, menthyl, bromine, chlorine or methoxy. The benzothiazepine derivative has good antibacterial effect and may act as a potential antibacterial agent as a potential antibacterial agent.

Description

technical field [0001] The invention relates to the synthesis and application fields of heterocyclic compounds, in particular to a quinothiopyran derivative and its synthesis method and application. Background technique [0002] Quinolinothiopyran compounds are an important class of nitrogen-containing heterospirocyclic compounds. Quinolinothiopyranoside compounds have strong pharmacological, physiological and biological activities, such as anticancer, anti-inflammatory, antibacterial, antipsychotic, analgesic and antitumor and other important physiological activities. Such compounds have a wide range of applications in the fields of catalysis and materials. Therefore, it is of great significance to synthesize and study quinolinothiopyran compounds. [0003] [0004] There are several recent approaches to the synthesis of quinothiopyran derivatives: [0005] (1) In 2013, chemist Zhenghong Zhou reported that the chiral Quinothiopyran derivatives (Adv. Synth. Catal. 201...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A01N43/90A01P3/00
CPCA01N43/90C07D495/04
Inventor 谢建武唐婷王梦雪
Owner ZHEJIANG NORMAL UNIVERSITY
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