Isoquinoline derivative with hypoglycemic activity and application thereof

A technology of derivatives and isoquinoline, applied in the field of 3-aryl isoquinoline and 4-aryl quinoline derivatives and their preparation, can solve problems such as the research on non-hypoglycemic activity, and achieve good α-glucose The effect of glucosidase inhibitory activity and simple synthesis method

Pending Publication Date: 2019-05-21
TIANJIN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In summary, the above research no matter natural medicine or synthetic novel isoquinoline derivatives is different from the structure of the derivatives of the present invention, and most of the above researches are antibacterial experiments and antitumor experiments, and have no effect on hypoglycemic active research

Method used

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  • Isoquinoline derivative with hypoglycemic activity and application thereof
  • Isoquinoline derivative with hypoglycemic activity and application thereof
  • Isoquinoline derivative with hypoglycemic activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Synthesis of 4-(6,8-dimethylisoquinolin-3-yl)benzonitrile (compound 3a).

[0100]

[0101] (1) At 0°C, POCl 3 Add (1.5eq) dropwise to DMF (1.5eq), rise to room temperature after solidification, add 3,5-dimethoxyphenylacetonitrile (1.0eq), react at 65°C for 1h until the reaction solidifies into yellow, monitor the reaction after completion , with saturated NaHCO 3 Extract with ethyl acetate, collect organic phase and dry, silica gel column chromatography obtains light yellow product;

[0102] (2) Under the protection of argon, dissolve the dried product (1.0eq.) obtained in step (1) in toluene, add 4-cyanophenylboronic acid (1.2eq.), PdCl 2(dppf) (0.05eq.), cesium carbonate (3eq), react at 125°C for about 6h, after the reaction is complete, dilute with ethyl acetate, wash with water, and wash the organic layer with Na 2 SO 4 After drying and filtering, the solvent was evaporated to dryness and purified by silica gel column chromatography to obtain the product 3. ...

Embodiment 2

[0105] Synthesis of 3-(4-fluorophenyl)-6,8-dimethoxyisoquinoline (compound 3b).

[0106]

[0107] The synthetic method of embodiment 2 is the same as the synthetic method of above-mentioned embodiment 1.

[0108] Yield: 35%; Structural parameters: 1 H NMR (400MHz, CDCl 3 )δ9.46(s,1H),8.06(dd,J 1 =5.6Hz,J 2 =8.8Hz, 2H), 7.81(s, 1H), 7.16(t, J=8.8Hz, 2H), 6.66(d, J=2.0Hz, 1H), 6.48(d, J=2.0Hz, 1H), 3.99(s,3H),3.93(s,3H), such as figure 2 shown.

Embodiment 3

[0110] Synthesis of 6,8-dimethoxy-3-(4-(trifluoromethyl)phenyl)isoquinoline (compound 3c).

[0111]

[0112] The synthetic method of embodiment 3 is the same as the synthetic method of above-mentioned embodiment 1.

[0113] Yield: 35%; Structural parameters: 1 H NMR (400MHz, CDCl 3 )δ9.50(s,1H),8.20(d,J=8.0Hz,2H),7.90(s,1H),7.73(d,J=8.4Hz,2H),6.69(d,J=1.6Hz, 1H), 6.52(d, J=1.6Hz, 1H), 4.00(s, 3H), 3.94(s, 3H), such as image 3 shown.

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Abstract

The invention relates to an isoquinoline derivative with hypoglycemic activity. The isoquinoline is a 3-arylisoquinoline derivative and / or 4-arylquinoline derivative. The general molecular formula ofthe 3-arylisoquinoline derivative is as shown in formula I; and the general molecular formula of the 4-arylquinoline derivative is as shown in the formula II. In the general formula I, R1 is 6,8-dimethoxy, 6,8-dihydroxy, 6-hydroxy-8-methoxy or 6-methoxy-8-hydroxy; and R2 is substituted or non-substituted furan, pyrrole, pyrimidine or phenyl. In the general formula II, R1 is 6,7-dimethoxy; R2 is substituted or non-substituted furan, pyrrole, pyrimidine or phenyl. The isoquinoline derivative with hypoglycemic activity is synthesized for the first time, and it is found that the isoquinoline derivative with hypoglycemic activity has good alpha-glucosidase inhibitory activity. The derivative has good alpha-glucosidase inhibitory activity, can be applied to preparation of anti-diabetic medicines, and opens up a novel research direction of diabetes drugs.

Description

technical field [0001] The invention belongs to the technical field of new compound synthesis and drug application, in particular to 3-arylisoquinoline and 4-arylquinoline derivatives and their preparation method and application. Background technique [0002] Isoquinoline and its derivatives are an important class of heterocyclic compounds, which exist in many natural products. In 1848, papaverine, which was first extracted from Papaveraceae, is a natural product compound with an isoquinoline ring structure that inhibits fungi and viruses, and is still an important antispasmodic until now. [0003] In recent years, the isoquinoline skeleton is often used to design active structural groups in drug molecules, such as atracurium, nomifensine, moxavirin, demoxiline (methyl papaverine), isoquinacaine Wait. The research on the total synthesis and partial structure modification, structure-activity relationship and drug activity of isoquinoline and its derivatives is becoming more...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/18C07D217/20C07D405/04A61P3/10
Inventor 郁彭孙华郑航陈明珠汪海波王朝昕张一楠马玉娇
Owner TIANJIN UNIV OF SCI & TECH
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