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Isoquinoline-1,3(2h,4h)-dione containing cycloalkylnitrile group and its production method and use

A technology containing cycloalkyl nitrile and isoquinoline, which is applied in the fields of urinary system diseases, antineoplastic drugs, organic chemistry, etc., to achieve the effects of high yield, simple reaction operation and low cost

Inactive Publication Date: 2018-01-02
JISHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] So far, isoquinoline-1,3(2 H ,4 H )-diketone synthesis method has not been reported yet, we found that benzamide compounds can be combined with 1,1 ， -Azobicyclohexanenitrile undergoes a tandem addition / cyclization reaction under mild reaction conditions to efficiently introduce cyclohexanecarbonitrile groups into isoquinoline-1,3(2 H ,4 H )-diketone

Method used

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  • Isoquinoline-1,3(2h,4h)-dione containing cycloalkylnitrile group and its production method and use
  • Isoquinoline-1,3(2h,4h)-dione containing cycloalkylnitrile group and its production method and use
  • Isoquinoline-1,3(2h,4h)-dione containing cycloalkylnitrile group and its production method and use

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preparation example Construction

[0042] According to the preparation method in the foregoing examples, the following can also be prepared N -Isopropionyl- N -Alkylbenzamide derivatives (II), the general reaction formula is as follows:

[0043]

[0044] R in the general reaction formula 1 , R 2 Can be as shown in the following groups:

[0045] 1: R 1 = H, R 2 = n -Bu

[0046] 2: R 1 = H, R 2 = i -Pr

[0047] 3: R 1 = H, R 2 = Me

[0048] 4: R 1 = 4-Cl,R 2 = n -Bu

[0049] 5: R 1 = 4-Cl,R 2 = i -Pr

[0050] 6: R 1 = 4-F, R 2 = CH 2 CO 2 Et

[0051] 7: R 1 = 4-F, R 2 = Me

[0052] 8: R 1 = 4-Me,R 2 = n -Bu

[0053] 9: R 1 = 4-Me,R 2 = CH 2 Ph

[0054] 10: R 1 = 2-Me,R 2 = n -Bu

[0055] 11: R 1 = 2-Me,R 2 = i -Pr

[0056] 12: R 1 = 4-Br, R 2 = n -Bu

[0057] 13: R 1 = 4-OMe, R 2 = i -Pr

[0058] 14: R 1 = 3-Cl, R 2 = n -Bu

[0059] 15: R 1 = 3-Cl, R 2 = Me

[0060] 16: R 1 = 4-CF 3 , R 2 = n -Bu

[0061] 17: R 1 ...

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Abstract

The invention discloses an isoquinoline-1,3(2H,4H)-diketone compound containing a naphthenic nitrile group, and a preparation method and use of the isoquinoline-1,3(2H,4H)-diketone compound. The isoquinoline-1,3(2H,4H)-diketone compound has a structure as shown in formula (I); the preparation method takes N-isobutylene acyl-N-alkyl benzamide as a reaction starting material, 1,1'-azobis dicyclohexyl nitrile as a free radical source material, K3PO4 as alkali and dimethyl formamide (DMF) as a solvent, and comprises the steps of carrying out a reaction at the temperature of 85 DEG C in an air environment; after the reaction is carried out for 8 hours, separating and purifying by column chromatography or thin-layer chromatography to obtain the isoquinoline-1,3(2H,4H)-diketone compound. The compounds has a very high inhibition effect for prostate cancer cells (LNCap cells), and particularly, one or two of the compounds are very promising, so that an excellent opportunity is provided for finding out a lead compound for treating prostatic cancer; furthermore, the preparation method is simple in operation of a synthesis reaction, does not need any metal catalyst, and is mild in reaction system, simple in conditions, low in cost and high in yield, thus having great popularization and application values.

Description

technical field [0001] The invention relates to a class of isoquinoline-1,3(2H,4H)-dione containing a cycloalkylnitrile group and its preparation method and use. Background technique [0002] Among many heterocyclic compounds, isoquinolinones and their derivatives have attracted widespread attention due to their remarkable pharmacological and biological activities, and they exhibit important physiological activities, such as analgesia, antitumor, HIV-I RT inhibitors, 5 -HT 3 receptor antagonists, etc. Therefore, the development of nitrile-substituted isoquinoline-1,3(2 H, 4 H )-diketone compound synthesis method has important practical and theoretical value. [0003] So far, isoquinoline-1,3(2 H ,4 H )-diketone synthesis method has not been reported yet, we found that benzamide compounds can be combined with 1,1 ， -Azobicyclohexanenitrile undergoes a tandem addition / cyclization reaction under mild reaction conditions to efficiently introduce cyclohexanecarbonitrile gr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/24A61P35/00A61P13/08
CPCC07D217/24
Inventor 唐石邓佑林李捷李增增
Owner JISHOU UNIVERSITY