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3,4-dihydro-1H-spiro[naphthalene-2,1'-thienochromene] derivative and synthesis method and application thereof

A synthesis method and technology of derivatives, which are applied in the fields of botanical equipment and methods, applications, biocides, etc., to achieve the effects of novel structure, wide application range and high yield

Active Publication Date: 2019-02-01
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] A new type of heterocyclic compound is constructed by chemically reacting the coumarin skeleton, thiophene skeleton and other molecules. This heterocyclic compound contains both coumarin and thiophene skeletons, which has not been reported yet.

Method used

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  • 3,4-dihydro-1H-spiro[naphthalene-2,1'-thienochromene] derivative and synthesis method and application thereof
  • 3,4-dihydro-1H-spiro[naphthalene-2,1'-thienochromene] derivative and synthesis method and application thereof
  • 3,4-dihydro-1H-spiro[naphthalene-2,1'-thienochromene] derivative and synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] At 25°C, add coumarin derivative 1a (309mg, 1.1mmol), 2-bromotetralone 2a (224mg, 1mmol), and 5ml of acetonitrile into a 10ml reaction flask in turn, followed by addition of hydrogen Sodium (48mg, 1.2mmol), stirred for 12h. Then the solvent was removed under reduced pressure, and column chromatography was carried out with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate was 6:1) as eluent to obtain 3,4-dihydro- 1H-spiro[naphthalene-2,1'-thienochromene]-1,4'-dione derivative II (225 mg, yield 53%). The reaction equation is as follows:

[0039]

[0040] The structure of the 3,4-dihydro-1H-spiro[naphthalene-2,1'-thienochromene]-1,4'-dione derivative II obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600MHz, CDCl 3 )δ8.14(d, J=7.8Hz, 1H), 7.63(dd, J=11.5, 4.1Hz, 1H), 7.60(t, J=7.3Hz, 1H), 7.49(d, J=8.3Hz, 1H), 7.41(t, J=7.6Hz, 1H), 7.32(dt, J=7.5, 5.2Hz, 4...

Embodiment 2

[0042] At 25°C, add coumarin derivative 1b (346mg, 1.1mmol), 2-bromonalone 2a (224mg, 1mmol), and 5ml of acetonitrile into a 10ml reaction flask in turn, followed by addition of hydrogen Sodium (48mg, 1.2mmol), stirred for 12h. 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 6:1) was used as eluent to carry out column chromatography to obtain 3,4-dihydro- 1H-spiro[naphthalene-2,1'-thienochromene]-1,4'-dione derivative III (202 mg, yield 44%). The reaction equation is as follows:

[0043]

[0044] The structure of the 3,4-dihydro-1H-spiro[naphthalene-2,1'-thienochromene]-1,4'-dione derivative III obtained above was identified by nuclear magnetic resonance, 1 H NMR (600MHz, CDCl 3 )δ8.14(d, J=7.8Hz, 1H), 7.65(dd, J=11.5, 4.2Hz, 1H), 7.60(t, J=7.5Hz, 1H), 7.50(d, J=8.4Hz, 1H), 7.41(dd, J=14.1, 7.3Hz, 2H), 7.31(d, J=7.8Hz, 2H), 7.26–7.20(m, 2H), 7.08–7...

Embodiment 3

[0046] At 25°C, add coumarin derivative 1c (346mg, 1.1mmol), 2-bromonalone 2a (224mg, 1mmol), and 5ml of acetonitrile into a 10ml reaction flask in turn, followed by addition of hydrogen Sodium (48mg, 1.2mmol), stirred for 12h. 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 6:1) was used as eluent to carry out column chromatography to obtain 3,4-dihydro- 1H-spiro[naphthalene-2,1'-thienochromene]-1,4'-dione derivative IV (243 mg, yield 53%). The reaction equation is as follows:

[0047]

[0048] The structure of the 3,4-dihydro-1H-spiro[naphthalene-2,1'-thienochromene]-1,4'-dione derivative IV obtained above was identified by nuclear magnetic resonance, 1 H NMR (600MHz, CDCl 3 )δ8.17–8.12(m,1H),7.67–7.59(m,2H),7.52–7.48(m,1H),7.43(t,J=7.6Hz,1H),7.32(dd,J=11.3, 4.5Hz, 2H), 7.28–7.23(m, 2H), 7.12–7.08(m, 1H), 7.05(t, J=2.0Hz, 1H), 6.94–6.90(m, 1H), 3...

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Abstract

The invention discloses a 3,4-dihydro-1H-spiro[naphthalene-2,1'-thiophene chromene]derivative having antibacterial activity and a synthesis method and an application thereof. The structure of the 3,4-dihydro-1H-spiro [naphthalene-2,1'-thiophene chromene]-1,4'-dione derivative is represented as a formula (I), wherein R<1> is selected from hydrogen, chlorine, bromine or methoxy; R<2> is selected from hydrogen, chlorine, bromine, methyl, methoxy or trifluoromethyl; and R<3> is selected from hydrogen, chlorine, bromine, methyl, methoxy or trifluoromethyl. The 3,4-dihydro-1H-spiro[naphthalene-2,1'-thiophene chromene]-1, 4'-dione derivative has 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 3,4-dihydro-1H-spiro[naphthalene-2,1'-thienochromene]-1,4'-dione derivative and its synthesis methods and applications. Background technique [0002] [0003] Formula 1 coumarin skeleton and thiophene skeleton [0004] The coumarin skeleton (Formula 1) exists in many natural products and drugs [(a) M.Miski, J.Jakupovic, Cyclic farnesyl-coumarin and farnesyl-chromone derivatives from Ferulacommunis subsp.Communis, Phytochemistry, 1990, 29, 1995 -1998. (b) N. Schuster, C. Christiansen, J. Jakupovic, M. Mungai, An unusual [2+2] cycloloadduct of terpenoidcoumarin from Ethulia vernonioides, Phytochemistry, 1993, 34, 1179-1181.]. They have been reported to have various biological activities, such as anticoagulant, insecticidal, anthelmintic, hypnotic, antifungal, phytoalexin, and HIV protease inhibitory effects. [(a)A.A.Deana,2-(Aminomethyl)phenols, a new clas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10A01N43/90A01P3/00A01P1/00
CPCA01N43/90C07D493/10
Inventor 谢建武王经
Owner ZHEJIANG NORMAL UNIVERSITY
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