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1,3-benzothiazin-2-one derivatives having antibacterial activity, and synthetic method and applications thereof

A benzothiazine and antibacterial activity technology, applied in the field of 1,3-benzothiazine-2-one derivatives and their synthesis, can solve the problems of complex substrates, harsh reaction conditions, etc. Easy to operate, flexible response time

Active Publication Date: 2018-10-09
惠州拓康生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above methods for synthesizing 1,3-benzothiazin-2-one derivatives all have certain shortcomings, such as complex substrates, harsh reaction conditions, etc.
In particular, the current method for synthesizing 1,3-benzothiazin-2-one derivatives has not been reported in the literature

Method used

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  • 1,3-benzothiazin-2-one derivatives having antibacterial activity, and synthetic method and applications thereof
  • 1,3-benzothiazin-2-one derivatives having antibacterial activity, and synthetic method and applications thereof
  • 1,3-benzothiazin-2-one derivatives having antibacterial activity, and synthetic method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 65 o Under C, add the substituted α,β-unsaturated aldehyde derivative 1a (189 mg, 1 mmol ), 4 ml of methanol into a 10 ml reaction flask, and then add hydroxylamine hydrochloride 2 (210 mg, 3 mmol), The reaction was stirred for 24 hours. Then the solvent was removed under reduced pressure, and the eluent was subjected to column chromatography with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 5:1) to obtain 1,3-benzothiophene with the structural formula 3a Oxin-2-one derivative 3a (106 mg, yield 42%). The reaction equation is as follows:

[0037]

[0038] The structure of the 1,3-benzothiazin-2-one derivative 3a obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600 MHz, CDCl 3 ) δ 9.93 (s, 1H), 7.26 (td, J = 7.8, 1.3 Hz, 1H),7.16 (d, J = 6.7 Hz, 1H), 7.09 (td, J = 7.5, 0.9 Hz, 1H), 7.02 (d, J = 7.9Hz, 1H), 4.45 (t, J = 5.9 Hz, 1H), 4.16 ...

Embodiment 2

[0040] 65 o C, the substituted α,β-unsaturated aldehyde derivative 1b (203 mg, 1 mmol, ), 4 ml of methanol were sequentially added to a 10 ml reaction flask, followed by addition of hydroxylamine hydrochloride 2 (210 mg, 3 mmol) , and the reaction was stirred for 24 hours. Then the solvent was removed under reduced pressure, and the eluent was subjected to column chromatography with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 5:1) to obtain 1,3-benzothiophene with the structural formula 3b Oxin-2-one derivative 3b (96 mg, yield 36%). The reaction equation is as follows:

[0041]

[0042] The structure of the 1,3-benzothiazin-2-one derivative 3b obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600 MHz, CDCl 3 ) δ 9.65 (s, 1H), 7.06 (dd, J = 8.1, 1.2 Hz, 1H), 6.96 (s, 1H), 6.89 (d, J = 8.1 Hz, 1H), 4.47 (dd, J = 6.1, 5.7 Hz, 1H), 4.10(dd, J = 8....

Embodiment 3

[0044] 65 o C, the substituted α,β-unsaturated aldehyde derivative 1c (203 mg, 1 mmol, ), 4 ml of methanol were sequentially added to a 10 ml reaction flask, followed by addition of hydroxylamine hydrochloride 2 (210 mg, 3 mmol) , and the reaction was stirred for 24 hours. Then the solvent was removed under reduced pressure, and the eluent was subjected to column chromatography with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 5:1) to obtain 1,3-benzothiophene with the structural formula 3c Oxin-2-one derivative 3c (91 mg, yield 34%). The reaction equation is as follows:

[0045]

[0046] The structure of the 1,3-benzothiazin-2-one derivative 3c obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600 MHz, CDCl 3 ) δ 9.68 (s, 1H), 7.03 (d, J = 7.7 Hz, 1H), 6.92 –6.89 (m, 1H), 6.81 (s, 1H), 4.44 (t, J = 5.9 Hz, 1H), 4.12 (t, J = 7.8 Hz,1H), 3.33 (d, ...

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PUM

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Abstract

1,3-benzothiazin-2-one derivatives having antibacterial activity, and a synthetic method and applications thereof are disclosed. The structures of the derivatives are shown as a formula (I), wherein R1 is selected from hydrogen, chlorine, bromine, methyl or nitro. The derivatives have good antibacterial effect and can be used as a potential antibacterial agent.

Description

technical field [0001] The invention relates to the field of synthesis of heterocyclic compounds, in particular to a 1,3-benzothiazin-2-one derivative and its synthesis method and application. Background technique [0002] Benzothiazine is a class of heterocyclic compounds formed by combining a benzene ring and a six-membered sulfur nitrogen heterocycle. Studies have found that benzothiazine compounds have antibacterial, hypolipidemic, hypotensive, and anthelmintic properties [Ajani, O. O. Arch. Pharm. Chem. Life Science . 2012, 345 , 841.], antiviral [ (a) Suazo, P. A.; Tognarelli, E. I.; Kalergis, A. M.; Gonzalez, P. A. Med. Microbiol. Immunol. 2015, 204 , 161. (b) Chamoun, A. M.; Chockalingam, K.; Bobardt, M.; Simeon, R.; Chang, J.; Gallay, P.;Chen, Z. Antimicrob. Agents Chemother. 2012, 56 , 672. (c) Mizuhara, T.; Oishi, S.; Ohno, H.; Shimura, K.; Matsuoka, M.; Bioorg. Med. Chem. 2012, 20 , 6434.], antineoplastic [Saunthwal, R. K.; Patel, M.; Kumar, S.; Ver...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/08A01P1/00A01P3/00
CPCC07D279/08
Inventor 王贤洵谢建武刘天渝田旭熊小峰庄佳嘉庄佳娥庄柏润庄泽林王贤镔孙莹
Owner 惠州拓康生物科技有限公司
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