A kind of 4h-1,3-benzothiazine derivative with antibacterial activity and its synthesis method and application

A 4H-1, benzothiazine technology, applied in the directions of botanical equipment and methods, applications, biocides, etc., can solve the problems of complex substrates, harsh reaction conditions, low yields, etc., and achieves high yields, Easy to operate, cheap and easy to obtain solvent

Active Publication Date: 2020-11-06
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The above methods for synthesizing 4H-1,3-benzothiazine derivatives all have certain shortcomings, such as complex substrates, harsh reaction conditions, low yields, etc.

Method used

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  • A kind of 4h-1,3-benzothiazine derivative with antibacterial activity and its synthesis method and application
  • A kind of 4h-1,3-benzothiazine derivative with antibacterial activity and its synthesis method and application
  • A kind of 4h-1,3-benzothiazine derivative with antibacterial activity and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] At 25°C, substituted cinnamaldehyde derivative 1b (26.7mg, 0.1mmol), and 1ml of methanol were sequentially added to a 5ml reaction flask, followed by secondary amine 2a (11.0mg, 0.15mmol), and the reaction was stirred for 30 Second. Then the solvent was removed under reduced pressure, and the mixed solution of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 8:1) was used as eluent to carry out column chromatography to obtain 4H-1,3-benzene of structural formula such as 3ba. Thiazine derivative 3ba (33 mg, yield 98%). The reaction equation is as follows:

[0050]

[0051] The structure of the 4H-1,3-benzothiazine derivative 3ba obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600MHz, CDCl 3 )δ9.73(d,J=1.5Hz,1H),7.21(d,J=7.6Hz,1H),7.11–7.01(m,2H),5.02(dd,J=10.4,3.6Hz,1H), 3.61(d, J=91.2Hz, 4H), 2.95(ddd, J=17.4, 10.4, 2.2Hz, 1H), 2.68(dd, J=17.4, 3.6Hz, 1H), 1.96...

Embodiment 2

[0053] At 25°C, substituted cinnamaldehyde derivative 1c (18.9mg, 0.1mmol), and 1ml of methanol were sequentially added to a 5ml reaction flask, followed by secondary amine 2a (11.0mg, 0.15mmol), and the reaction was stirred for 30 Second. Then remove the solvent under reduced pressure, and carry out column chromatography with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate is 8:1) as the eluent to obtain 4H-1,3-benzene with a structural formula such as 3ca Thiazine derivative 3ca (33 mg, yield 93%). The reaction equation is as follows:

[0054]

[0055] The structure of the 4H-1,3-benzothiazine derivative 3ca obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600MHz, CDCl 3 )δ9.66(s,1H),7.31(dd,J=8.5,2.3Hz,1H),7.20(d,J=2.3Hz,1H),6.97(d,J=8.5Hz,1H),4.45( dd,J=8.3,5.8Hz,1H),3.66(s,2H),3.53(s,2H),2.99(ddd,J=17.9,8.4,1.5Hz,1H),2.82(dd,J=17.8, 5.8Hz,1H),1.97–1.91(...

Embodiment 3

[0057] At 25°C, substituted cinnamaldehyde derivative 1d (20.3mg, 0.1mmol), and 1ml of methanol were sequentially added to a 5ml reaction flask, followed by secondary amine 2a (11.0mg, 0.15mmol), and the reaction was stirred for 30 Second. 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 8:1) as the eluent to obtain 4H-1,3-benzene with a structural formula such as 3da. Thiazine derivative 3da (26 mg, yield 95%). The reaction equation is as follows:

[0058]

[0059] The structure of the 4H-1,3-benzothiazine derivative 3da obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600MHz, CDCl 3 )δ9.68(s,1H),7.06–7.00(m,2H),6.87(s,1H),4.44(dd,J=8.4,5.8Hz,1H),3.71–3.64(m,2H),3.54 (s,2H),3.00(ddd,J=17.6,8.5,1.7Hz,1H),2.82(ddd,J=17.7,5.8,0.8Hz,1H),2.29(s,3H),1.9...

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Abstract

The invention discloses a 4H-1,3-benzothiazine derivative with antibacterial activity and a synthesis method and applications thereof. The structure of the 4H-1,3-benzothiazine derivative is represented by the formula (I), wherein in the formula (I), R1 represents a hydrogen atom, a chlorine atom, a bromine atom, or a methoxyl group, and R2 represents a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, a methoxyl group, or a trifluoromethyl group. The 4H-1,3-benzothiazine derivative has a good antibacterial effect and can be used as a potential antiseptic.

Description

technical field [0001] The invention relates to the field of synthesis of heterocyclic compounds, in particular to a 4H-1,3-benzothiazine derivative and its synthesis method and application. Background technique [0002] Compounds with 4H-1,3-benzothiazine have good pharmacological and biological activities ((a) Schilling, S.; Cynis, H.; Hoffmann, T.; Demuth, H.-U.US Pat. Appl.US 068699,2009; Chem.Abstr.2009,150,322579.(b) Anzini, M.; Giordani, A.; Makovec, F.; Cappelli, A.; Vomero, S.; Caselli, G.; Rovati, G.; Lucio, C. PCT Int. Pat. Appl. 040331, 2009; Chem. Abstr. 2009, 150, 374522. (c) Reynisson, J.; Court, W.; O'Neill, C.; Day, J.; Patterson, L.; McDonald, E.; Workman, P.; Katan, M.; Eccles, S.A. Bioorg. Med. Chem. 2009, 17, 3169.). For example, these compounds possess diuretic, anticancer and antiallergic activities. There are also many reports on the synthesis of such compounds ((a) Beilenson, B.; Hamer, F.M.J.Chem.Soc.1942, 98. (b) Besson, T.; Guillaumet, G.; La...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D279/08A01N43/86A01P1/00A01P3/00
CPCA01N43/86C07D279/08
Inventor 谢建武董建连卫培顺
Owner ZHEJIANG NORMAL UNIVERSITY
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