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1,2,3,4-tetrahydroisoquinoline derivatives, synthesis method and applications thereof

A technology of tetrahydroisoquinoline and a synthesis method, which is applied in the field of medicine, can solve the problems that tetrahydroisoquinoline cannot be rapidly derivatized, and tetrahydroisoquinoline derivatives with diverse structures cannot be quickly obtained, and the reaction conditions are mild. , Simple operation, simple processing effect

Inactive Publication Date: 2016-03-23
SHAOXING UNIVERSITY
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0006] The 1,2,3,4-tetrahydroisoquinoline derivatives prepared by the present invention solve the problem that existing methods cannot rapidly derivatize the structure of tetrahydroisoquinoline, and cannot quickly obtain tetrahydroisoquinoline with various structures Disadvantages such as morphine derivatives

Method used

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  • 1,2,3,4-tetrahydroisoquinoline derivatives, synthesis method and applications thereof
  • 1,2,3,4-tetrahydroisoquinoline derivatives, synthesis method and applications thereof
  • 1,2,3,4-tetrahydroisoquinoline derivatives, synthesis method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In a 10mL round bottom flask, add magneton, acetonitrile (3mL), 1,2,3,4-tetrahydroisoquinoline (0.6mmol), 4-methylbenzaldehyde (0.72mmol), formic acid (0.72mmol ) and cyclohexylisonitrile (0.72mmol), the reaction mixture was stirred at room temperature for 48 hours. A white solid appeared in the reaction solution, and the solid was filtered and washed with a mixture of ethyl acetate and petroleum ether (1:1 by volume), and then dried by a vacuum oil pump to obtain a white solid product (yield 88%). Product by 1 H-NMR and 13 C-NMR detection is determined to be desired product (numbering: 5a), 1 H-NMR and 13 C-NMR data, mass spectrum and structure are as follows:

[0028]

[0029] N-cyclohexyl-2-(3,4-dihydroisoquinolin-2(1H)-yl-2-p-tolylacetamide:

[0030] 1 HNMR (400MHz, CDCl 3 )δppm7.27(d, J=8.0Hz, 2H), 7.16-7.09(m, 6H), 6.92(d, J=7.2Hz, 1H), 3.92(s, 3H), 3.82-3.76(m, 1H ),3.58and3.51(ABq,J=15.2,14.8Hz,2H),2.94-2.89(m,2H),2.86-2.78(m,1H),2.72-2.66(m,1H),2.35(...

Embodiment 2

[0032] In a 10mL round bottom flask, add magneton, acetonitrile (3mL), 1,2,3,4-tetrahydroisoquinoline (0.6mmol), 2-bromobenzaldehyde (0.72mmol), formic acid (0.72mmol) and cyclohexylisonitrile (0.72 mmol), and the reaction mixture was stirred at room temperature for 72 hours. A white solid appeared in the reaction solution, and the solid was filtered and washed with a mixture of ethyl acetate and petroleum ether (volume ratio 1:1), and then dried by a vacuum oil pump to obtain a white solid product (yield 76%). Product by 1 H-NMR and 13 C-NMR detection is determined to be desired product (numbering: 5b), 1 H-NMR and 13 C-NMR data, mass spectrum and structure are as follows:

[0033]

[0034] N-cyclohexyl-2-(3,4-dihydroisoquinolin-2(1H)-yl-2-(2-bromophenyl)acetamide:

[0035] 1 HNMR (400MHz, CDCl 3 )δppm7.62(dd, J=8.0,1.2Hz,1H),7.46(dd,J=8.0,2.0Hz,1H),7.31(ddd,J=7.2,7.2,0.4Hz,1H),7.20-7.09 (m,5H),6.94(d,J=7.2Hz,1H),4.76(s,3H),3.87-3.80(m,1H),3.75and3.60(ABq,J=14.8,14...

Embodiment 3

[0037] In a 10mL round bottom flask, add magneton, acetonitrile (3mL), 1,2,3,4-tetrahydroisoquinoline (0.6mmol), 4-methoxybenzaldehyde (0.72mmol), formic acid (0.72 mmol) and cyclohexylisonitrile (0.72 mmol), the reaction mixture was stirred at room temperature for 72 hours. A white solid appeared in the reaction solution, and the solid was filtered and washed with a mixture of ethyl acetate and petroleum ether (1:1 by volume), and dried by a vacuum pump to obtain the product (60% yield). Product by 1 H-NMR and 13 C-NMR detection is determined to be desired product (numbering: 5c), 1 H-NMR and 13 C-NMR data, mass spectrum and structure are as follows:

[0038]

[0039] N-cyclohexyl-2-(3,4-dihydroisoquinolin-2(1H)-yl-2-(4-methoxyphenyl)acetamide: 1 HNMR (400MHz, CDCl 3 )δppm7.29(d, J=8.8Hz, 2H), 7.15-7.08(m, 4H), 6.92(d, J=7.2Hz, 1H), 6.87(d, J=8.8Hz, 2H), 3.90( s,1H),3.80(s,3H),3.83-3.76(m,1H),3.56&3.50(ABq,J=15.6,15.6Hz,2H),2.93-2.88(m,2H),2.83-2.78 (m,1H),2.71-2.65(...

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Abstract

The invention discloses 1,2,3,4-tetrahydroisoquinoline derivatives, a synthesis method and applications thereof. The synthesis method is characterized in that 1,2,3,4-tetrahydroisoquinoline, aldehyde, formic acid, and isonitrile are taken as the raw materials, the raw materials are stirred in an organic solvent for 48 to 72 hours at a certain temperature to carry out reactions, and then the reaction product is filtered, washed, and dried in vacuum to obtain high purity 1,2,3,4-tetrahydroisoquinoline derivatives. The synthesis method has the advantages of simple and easily-available raw materials, mild reaction conditions, and simple operation. The composition of raw materials can be easily changed to obtain 1,2,3,4-tetrahydroisoquinoline derivatives with various structures. The 1,2,3,4-tetrahydroisoquinoline derivatives can be used to prepare antitumor drugs.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and in particular relates to a 1,2,3,4-tetrahydroisoquinoline derivative and a synthesis method and application thereof. technical background: [0002] Tetrahydroisoquinoline is an important class of heterocyclic compounds, many of its derivatives have a variety of important biological activities. At present, the derivatization of tetrahydroisoquinoline mainly relies on the traditional one-step-one-modification method. The synthetic route is long, the synthetic efficiency is low, the overall synthesis yield is low, and it is difficult to obtain derivatives with diverse structures. 1,2,3,4-Tetrahydroisoquinoline itself is a common compound with many sites available for chemical reactions. Therefore, in recent years, some efficient methods have been developed to modify 1,2,3,4-tetrahydroisoquinoline in multiple places by one-pot method to obtain tetrahydroisoquinoline with diverse structures, an...

Claims

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Application Information

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IPC IPC(8): C07D217/04A61P35/00
CPCC07D217/04
Inventor 朱余玲
Owner SHAOXING UNIVERSITY
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