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A kind of double spiro isatin furan derivative with antibacterial activity and its synthesis method and application

A technology of furan derivatives and synthesis methods, applied in the field of bispiroisatin furan derivatives and their synthesis, can solve the problems of antibacterial properties of compounds that have not been studied, and achieve the effects of flexible reaction time, high yield, and wide application range

Active Publication Date: 2018-07-03
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods have synthesized a series of spiro isatin furan derivatives, but few bispiro isatin furan derivatives have been synthesized, and the antibacterial properties of such compounds have not been studied

Method used

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  • A kind of double spiro isatin furan derivative with antibacterial activity and its synthesis method and application
  • A kind of double spiro isatin furan derivative with antibacterial activity and its synthesis method and application
  • A kind of double spiro isatin furan derivative with antibacterial activity and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] In a 5 ml reaction tube, add 1 ml of tetrahydrofuran, substituted 3-hydroxyisatin 1a (36 mg, 0.15 mmol, 1.5 eq), electron-deficient olefin 2a (20 mg, 0.1 mmol, 1.0 eq) and cinchonine (6 mg, 0.02 mmol ) was stirred at 0° C. for 12 h. 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 8:1) to obtain the double spiro isatin furan derivative of structural formula such as 3aa 3aa (31 mg, 71% yield). The reaction equation is as follows:

[0044]

[0045] The structure of the bis-helical isatin furan derivative 3aa obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (400MHz, DMSO) δ10.44(s,1H),7.99(s,2H),7.62(d,J=7.6Hz,1H),7.38(d,J=7.6Hz,1H),7.31–7.20 (m,2H),7.17(dd,J=10.8,7.2Hz,3H),7.05(s,1H),6.94(s,1H),6.80–6.70(m,3H),6.60(d,J=7.9 Hz,1H)...

Embodiment 2

[0047] In a 5 ml reaction tube, add 1 ml of tetrahydrofuran, substituted 3-hydroxyisatin 1a (36 mg, 0.15 mmol, 1.5 eq), electron-deficient olefin 2b (25 mg, 0.1 mmol, 1.0 eq) and cinchonine (6 mg, 0.02 mmol ) was stirred at 0° C. for 12 h. Subsequently, the solvent is removed under reduced pressure, and column chromatography is carried out with a mixed solution of sherwood oil and ethyl acetate (the volume ratio of sherwood oil and ethyl acetate is 8:1) as eluent to obtain a double-spirited isatin furan derivative of structural formula such as 3ab 3ab (25 mg, 51% yield). The reaction equation is as follows:

[0048]

[0049] The structure of the bis-helical isatin furan derivative 3ab obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1H NMR (600MHz, DMSO) δ7.98 (s, 2H), 7.53 (d, J = 7.6Hz, 1H), 7.39 (d, J = 7.5Hz, 1H), 7.36–7.31 (m, 1H), 7.24 (td, J=7.8,1.0Hz,1H),7.18(d,J=7.2Hz,1H),7.15(t,J=7.3Hz,2H),7.01(dt,J=20.9,7.6Hz,2...

Embodiment 3

[0051] In a 5 ml reaction tube, add 1 ml of tetrahydrofuran, substituted 3-hydroxyisatin 1a (36 mg, 0.15 mmol, 1.5 eq), electron-deficient olefin 2c (29 mg, 0.1 mmol, 1.0 eq) and cinchonine (6 mg, 0.02 mmol ) was stirred at 0° C. for 12 h. Subsequently, the solvent is removed under reduced pressure, and the eluent is carried out by column chromatography with a mixture of petroleum ether and ethyl acetate (the volume ratio of petroleum ether and ethyl acetate is 8:1) to obtain a double-spirited isatin furan derivative of structural formula such as 3ac 3ac (31 mg, 58% yield). The reaction equation is as follows:

[0052]

[0053] The structure of the double-helical isatin furan derivative 3ac obtained above was identified by nuclear magnetic resonance and high-resolution mass spectrometry, 1 H NMR (600MHz, DMSO) δ8.05(s, 2H), 7.56(d, J=7.6Hz, 1H), 7.42(d, J=7.5Hz, 1H), 7.31(td, J=7.8, 1.2Hz ,1H),7.22(td,J=7.8,1.2Hz,1H),7.16–7.10(m,3H),7.08(d,J=7.7Hz,1H),7.07–7.03(m,2H),6.9...

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Abstract

The invention discloses double-spiro isatin furan derivatives with antibacterial activity as well as a synthesis method and an application thereof. The structural formula of the double-spiro isatin furan derivatives is shown in formula (I) defined in the description, wherein R<1> is selected from hydrogen, benzyl group, C1-C4 alkyl group and allyl group; R<2> is selected from hydrogen, methyl group and chlorine; R<3> is selected from hydrogen, benzyl group, C1-C4 alkyl group and allyl group; and R<4> is selected from hydrogen, methyl group and chlorine. The double-spiro isatin furan derivatives have a 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 bis-helicoisatin furan derivative and its synthesis method and application. Background technique [0002] Spiroisatin heterocyclic compounds, especially spiroisatin furan, have many important physiological activities in inhibiting tumor cell growth, anti-anxiety, anti-inflammation, analgesia, blood pressure reduction and insecticide. Therefore, it is meaningful to synthesize and study spiroisatin furan derivatives. The structure of spirofuran isatin is shown in the following formula: [0003] [0004] Several methods for the synthesis of spiroisatin furan derivatives have been mainly reported at present: [0005] (1) In 2015, chemist Rong Zhou reported the spiroisatin furan derivative (Chem.Commun., 2015, 51, 14663-14666). [0006] [0007] (2) In 2004, chemist Jian-Hua Xu reported that substituted isatins reacted with alkyne amines under light condi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/20A61K31/407A61P31/04A61P31/10A01N43/90A01P1/00A01P3/00
CPCA01N43/90C07D491/20Y02A50/30
Inventor 谢建武朱晓倩
Owner ZHEJIANG NORMAL UNIVERSITY
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