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A multi-substituted 1,2,3,4,8,8a-hexahydroquinoline compound and its preparation

A hexahydroquinoline, multi-substitution technology, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problems of preparation methods and applications that have not been reported in literature, and achieve low cost, fast reaction time, and simple operation Effect

Inactive Publication Date: 2019-12-31
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis method of multi-substituted tetrahydroquinolines has been reported in the literature, the preparation method and application of multi-substituted 1,2,3,4,8,8a-hexahydroquinoline compounds have not been reported in the literature

Method used

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  • A multi-substituted 1,2,3,4,8,8a-hexahydroquinoline compound and its preparation
  • A multi-substituted 1,2,3,4,8,8a-hexahydroquinoline compound and its preparation
  • A multi-substituted 1,2,3,4,8,8a-hexahydroquinoline compound and its preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Add K to a microwave tube equipped with a magneton under a nitrogen atmosphere 2 PtCl 4 (20.8mg, 0.05mmol), aminoalkyne I-a (101.5mg, 0.5mmol), chalcone II-a (208.0mg, 1.0mmol), then add 10mL of anhydrous methanol with a syringe, under microwave irradiation, react at 150°C for 10 After 10 minutes, TLC detected that the reaction was complete, and then subjected to silica gel column chromatography (eluent: petroleum ether / ethyl acetate=10:1), to obtain 118 mg of light yellow solid III-aa. 1 H NMR (500MHz, CDCl 3 )δ7.35(d, J=7.2Hz, 2H), 7.28(d, J=7.4Hz, 2H), 7.24(d, J=0.9Hz, 2H), 7.20(dd, J=8.5, 7.0Hz, 3H), 7.15–7.11(m, 1H), 6.98(d, J=8.9Hz, 2H), 6.84(d, J=9.0Hz, 2H), 6.03(d, J=2.1Hz, 1H), 3.79( s,3H),3.60–3.50(m,3H),3.16(ddd,J=16.5,9.0,2.2Hz,1H),2.83(dd,J=16.5,4.9Hz,1H),2.07(d,J= 5.7Hz, 2H), 1.78–1.68(m, 2H); 13 C NMR (125MHz, CDCl 3 )δ155.00,144.89,142.43,140.87,135.92,132.96,128.39,128.25,127.82,126.80,126.33,125.15,124.46,121.91,116.02,114.29,55.52,52...

Embodiment 2

[0037] Add K to a microwave tube equipped with a magneton under a nitrogen atmosphere 2 PtCl 4 (20.8mg, 0.05mmol), aminoalkyne I-a (0.5mmol), chalcone II-b (1.0mmol), then add 10mL of anhydrous methanol with a syringe, and react under microwave irradiation at 79°C for 10 minutes, and the reaction is complete by TLC After silica gel column chromatography (eluent: petroleum ether / ethyl acetate=10:1), 118 mg of light yellow solid was obtained. The structure was confirmed by high-resolution mass spectrometry, HRMS(ESI)[M+H]calculated for[C 30 h 32 NO3] + 454.2377, found 454.2373.

[0038]

Embodiment 3

[0040] Add K to a microwave tube equipped with a magneton under a nitrogen atmosphere 2 PtCl 4 (20.8mg, 0.05mmol), aminoalkyne I-a (0.5mmol), chalcone II-c (1.0mmol), then add 10mL of anhydrous methanol, under microwave irradiation, react at 150°C for 10 minutes, TLC detects that after the reaction is complete, the Silica gel column chromatography (eluent: petroleum ether / ethyl acetate=10:1) gave a pale yellow solid. The structure was confirmed by high-resolution mass spectrometry, HRMS(ESI)[M+H]calculated for[C 30 h 32 NO] + 422.2478, found 422.2478.

[0041]

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Abstract

The invention provides a polysubstituted 1,2,3,4,8,8a-hexahydroquinoline compound. A preparation method of the polysubstituted 1,2,3,4,8,8a-hexahydroquinoline compound comprises the following steps: adding potassium chloroplatinite, aminoacetylene and chalcone into a reaction flask, adding a solvent into the reaction flask, and obtaining a platinum-catalyzed target product under microwave irradiation. The polysubstituted 1,2,3,4,8,8a-hexahydroquinoline compound shows the effect of inhibiting the growth of tumor cells and can be applied to preparation of drugs for inhibiting the growth of tumor cells. The method is reasonable in design, high in yield, short in time and low in cost, and provides a compound with a brand new structure for research and development of the antitumor drugs. The structure general formula of the compound is as shown in the description.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a multi-substituted 1,2,3,4,8,8a-hexahydroquinoline compound and a preparation method. Background technique [0002] Nitrogen-containing heterocyclic compounds widely exist in natural products and bioactive molecules, and have great research value. Although the synthesis method of multi-substituted tetrahydroquinolines has been reported in the literature, the preparation method and application of multi-substituted 1,2,3,4,8,8a-hexahydroquinoline compounds have not been reported in the literature. Contents of the invention [0003] The object provided by the present invention is a multi-substituted 1,2,3,4,8,8a-hexahydroquinoline compound, the structure of which is shown in formula (I): [0004] [0005] in: [0006] R 1 , R 2 is hydrogen, alkyl (preferably C 1 ~C 6 alkyl), alkoxy (preferably methoxy, ethoxy), halogen. [0007] R 3 is hydrogen, alkyl (preferably C 1 ~C ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06C07D215/14C07D215/12A61P35/00
CPCC07D215/06C07D215/12C07D215/14
Inventor 马灿亮董晓武夏凡赖振成胡永洲
Owner ZHEJIANG UNIV