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2,3-condensed ring indoline derivative and synthesizing method and application thereof

A compound and unsubstituted technology, applied in the field of medicine, can solve the problems of poor compatibility of functional groups, limited substrates, complex raw materials, etc., and achieve the effects of high yield, simple and easy-to-control synthetic method, and short cycle time

Inactive Publication Date: 2017-10-20
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Strategies for constructing such frameworks can be achieved through palladium-catalyzed tandem reactions (Zhang, G.Z.; Catalano, V.J.; Zhang, L.M.J. Am. Chem. Soc. 2007, 129, 11358-11359.), oxidative coupling, intramolecular cyclization reactions (Zuo, Z.W.; Xie, W.Q.; Ma, D.W.J.Am.Chem.Soc.2010, 132, 13226-13228), etc., but these methods all have limited substrates, poor functional group compatibility, cumbersome steps and complicated raw materials, etc. insufficient

Method used

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  • 2,3-condensed ring indoline derivative and synthesizing method and application thereof
  • 2,3-condensed ring indoline derivative and synthesizing method and application thereof
  • 2,3-condensed ring indoline derivative and synthesizing method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Synthesize the 2,3-fused ring indoline derivatives of the present invention according to the following synthetic route.

[0049]

[0050] 2a:R 1 =H,R 2 =PhCH=CH,R 3 =H,R 4 =H,n=1;

[0051] 2b:R 1 =H,R 2 =PhCH=CH,R 3 =4-OMe,R 4 =H,n=1;

[0052] 2c:R 1 =H,R 2 =PhCH=CH,R 3 =4-Me,R 4 =H,n=1;

[0053] 2d:R 1 =H,R 2 =PhCH=CH,R 3 =4-tBu,R 4 =H,n=1;

[0054] 2e:R 1 =H,R 2 =PhCH=CH,R 3 =4-Cl,R 4 =H,n=1;

[0055] 2f:R 1 =H,R 2 =PhCH=CH,R 3 =4-F,R 4 =H,n=1;

[0056] 2g:R 1 =H,R 2 =PhCH=CH,R 3 = 4-CF 3 , R 4 =H,n=1;

[0057] 2h:R 1 =H,R 2 =PhCH=CH,R 3 = 4-CO 2 Me,R 4 =H,n=1;

[0058] 2i:R 1 =H,R 2 =PhCH=CH,R 3 =3-OMe,R 4 =H,n=1;

[0059] 2j:R 1 =H,R 2 =PhCH=CH,R 3 = 3-NO 2 , R 4 =H,n=1;

[0060] 2k:R 1 =H,R 2 =PhCH=CH,R 3 =3,5-Me,R 4 =H,n=1;

[0061] 2l:R 1 =H,R 2 =PhCH=CH,R 3 =2-Me,R 4 =H,n=1;

[0062] 2ab:R 1 =H,R 2 =(4-OMe)C 6 h 4 CH=CH,R 3 =H,R 4 =H,n=1;

[0063] 2ac:R 1 =H,R 2 =(4-Me)C 6 h 4 CH=CH,R 3 =...

Embodiment 2

[0142] Synthesize the 2,3-fused ring indoline derivatives of the present invention according to the following synthetic route.

[0143]

[0144] 2ba:R 1 =4-Br,R 2 =PhCH=CH,R 3 =4-Br,R 4 =H,n=1;

[0145] 2bb:R 1 =4-Br,R 2 =PhCH=CH,R 3 =3-Br,R 4 =H,n=1;

[0146] 2bc:R 1 =4-Br,R 2 =(3-Br)C 6 h 4 CH=CH,R 3 =4-Cl,R 4 =H,n=1;

[0147] 2bd:R 1 =4-Br,R 2 =(4-Me)C 6 h 4 CH=CH,R 3 =4-Cl,R 4 =Me,n=1;

[0148] 2be:R 1 =3-Cl,R 2 =Me,R 3 =4-Me,R 4 =H,n=1;

[0149] 2bf:R 1 =4-Br,R 2 =Me,R 3 =4-Me,R 4 =4-ClC 6 h 4 ,n=1;

[0150] 2bg:R 1 =3-Cl,R 2 =Me,R 3 =4-Me,R 4 =Me,n=1;

[0151] 2bh:R 1 =4-Br,R 2 =H,R 3 =4-Br,R 4 =H,n=1;

[0152] 2bi:R 1 =4-Br,R 2 =H,R 3 =3-Cl,R 4 =Me,n=2;

[0153] 2bj:R 1 =4-Br,R 2 =Me,R 3 =4-Br,R 4 =Me, n=1, X=N.

[0154] Take N-aryl α, β-unsaturated nitrone substrate 1 (0.2mmol) and place it in a reaction tube, add 2mL of organic solvent (wherein the organic solvents used for target 2ba-2bd are acetone, chloroform, n...

experiment example 1

[0175] Experimental Example 1: The 2,3-fused ring indoline derivatives of the present invention were tested for their inhibitory activity against various human tumor strains in vitro:

[0176] (1) Cell culture: MGC-803, HepG-2, NCI-H460, SKOV3, T24, 7702 cells were cultured in a medium containing 10% (volume ratio) fetal bovine serum and 1% (volume ratio) double antibody (containing penicillin and Streptomycin) in DMEM medium at 37°C, 5% CO 2 and 95% air incubator, and change the medium every other day. After the cells were confluent, they were subcultured and frozen.

[0177] (2) Seed plate: Take cells in the logarithmic growth phase, remove the old medium, wash twice with PBS, digest the cells with trypsin, add new medium after the cells become round, stop the digestion of the cells and pipette the suspended cells to prepare into a single cell suspension. Take an appropriate amount of cell suspension, add a certain amount of medium to dilute, inoculate into a 96-well plat...

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PUM

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Abstract

The invention discloses a 2,3-condensed ring indoline derivative and a synthesizing method and application thereof. The 2,3-condensed ring indoline derivative disclosed by the invention has a structure shown in the following formula (I). The synthesizing method of the 2,3-condensed ring indoline derivative mainly comprises the following steps: taking a compound shown in the following formula (II), putting into an organic solvent, and reacting in the presence of oxygen to obtain a target crude product. The synthesizing method of the derivative disclosed by the invention has easiness in control, short period and higher yield and avoids anhydrous and anaerobic conditions; furthermore, a part of the 2,3-condensed ring indoline derivative has certain antitumor activity. The compound of the structure shown by the formula (I) and the compound of the structure shown by the formula (II) are respectively shown in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to 2,3-condensed ring indoline derivatives and their synthesis methods and applications. Background technique [0002] Indole alkaloids are an important class of natural products. Due to their large number, complex structure and significant physiological activity, they have always been favored by synthetic chemists and medicinal chemists. [0003] The fused ring indoline skeleton, especially the 2,3-fused ring indoline is the core structure widely existing in indoline alkaloids, which plays a decisive role in the physiological activity and pharmacological activity of the compound, 2,3-fused The successful construction of the core skeleton of ring indoline is the focus and difficulty in the total synthesis of this kind of alkaloids, so the efficient construction of 2,3-fused ring indoline skeleton has always been one of the hotspots and difficulties in organic synthesis. Strategies...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/044C07D491/052C07D471/04A61P35/00
CPCA61P35/00C07D471/04C07D491/044C07D491/052
Inventor 莫冬亮马小盼吴思仪陈威利苏桂发
Owner GUANGXI NORMAL UNIV
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