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Biheterocyclic compound containing phenylselenyl substitution and its preparation and application

The technology of a phenylselenium compound, which is applied in the application field of preparing monoamine oxidase inhibitors, can solve the problems of high toxicity and side effects, single effect of monoamine oxidase, etc.

Active Publication Date: 2016-08-17
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since most of these drugs have relatively high toxicity and side effects, and have only a single effect on monoamine oxidase, it is a new goal of current research to seek MAOIs with low toxicity and good effects.

Method used

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  • Biheterocyclic compound containing phenylselenyl substitution and its preparation and application
  • Biheterocyclic compound containing phenylselenyl substitution and its preparation and application
  • Biheterocyclic compound containing phenylselenyl substitution and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1 Synthesis of oxadiazole derivatives VI-1-1. containing isoxazole

[0075]

[0076] 1) Add an equivalent amount of α-phenylselenopropionaldehyde (0.213g, 1mmol) and p-hydroxyphenylhydrazine (1mmol, 0.152g) into a round-bottomed flask containing 20ml of ethanol, stir to dissolve them completely, and then add 800μL of acetic acid , Reflux reaction under nitrogen protection for 3h. After TLC detected that the reaction was complete, the ethanol was drained, and 20mL CH 2 Cl 2 , with saturated Na 2 CO 3 solution (3 × 20 mL) washed with aqueous solution, anhydrous Na 2 SO 4 After drying and concentration, the crude product of intermediate product (Ⅲ) containing phenylselenyl group was obtained.

[0077] 2) The obtained product (Ⅲ) (1 mmol) was added to 5 mL of acetic anhydride, heated to reflux for 3 h under the protection of nitrogen, the color of the solution changed to orange and suspended solids were formed. After TLC detection reaction is complete, dra...

Embodiment 2

[0081] Example 2 Synthesis of oxadiazole derivatives VI-1-2. containing isoxazole

[0082]

[0083] 1) operate as embodiment 1 step 1

[0084] 2) operate as embodiment 1 step 2

[0085] 3) operate as embodiment 1 step 3

[0086] 4) Dissolve p-methoxybenzoxime (2mmol, 0.288g) and equivalent NCS (2mmol, 0.268g) in 20mL CH 2 Cl 2 After reacting at room temperature for 3h, compound V (1mmol, 0.388g) was added and triethylamine (2mmol, 0.28mL) was added dropwise to react for 6 hours. After most of the reaction was detected by TLC, subsequent treatment was as in step 4 of Example 1. VI-1-2. was obtained by thin-plate chromatography with a yield of 85%. Product characterization results are as follows:

[0087] 1 H NMR (400MHz, CDCl 3 )δ7.75-7.72(m,4H),7.68-7.64(m,4H),7.30(d,J=3.5Hz,2H),7.12-7.10(m,3H),6.99(d,J=8.8Hz ,1H),6.62(s,1H),5.24(s,2H),3.94-3.62(m,1H),3.85(s,3H),2.31(s,3H),1.34(d,J=7.2Hz, 3H); IRν max (cm -1 ):3120,2976,2920,2820,1665,1607,1580,1562,1504,1455,140...

Embodiment 3

[0088] Example 3 Synthesis of Isoxazole-containing Oxadiazole Derivatives VI-1-3.

[0089]

[0090] 1) operate as embodiment 1 step 1

[0091] 2) operate as embodiment 1 step 2

[0092] 3) operate as embodiment 1 step 3

[0093] 4) Dissolve p-chlorobenzoxime (2mmol, 0.313g) and equivalent NCS (2mmol, 0.268g) in 20mL CH 2 Cl 2 After reacting at room temperature for 3h, compound V (1mmol, 0.388g) was added and triethylamine (2mmol, 0.28mL) was added dropwise to react for 6 hours. After most of the reaction was detected by TLC, subsequent treatment was as in step 4 of Example 1. VI-1-3. was obtained by thin-plate chromatography with a yield of 71%. Product characterization results are as follows:

[0094] 1 H NMR (400MHz, CDCl 3 )δ7.68-7.60(m,4H),7.52(d,J=8.5Hz,2H),7.37–7.17(m,7H),6.92(d,J=8.5Hz,1H),6.35(s,1H ), 4.10(dd, J=49.1, 14.1Hz, 1H), 2.47(s, 2H), 2.40(s, 3H), 1.25(d, J=4.6Hz, 3H); IRν max (cm -1 ):3031,2922,2867,1884,1760,1618,1578,1551,1487,1445,1398,1376,1206...

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Abstract

The invention discloses a benzene-containing selenium group substituted diheterocyclic compound as well as preparation and application thereof. The structural formula of the benzene-containing selenium group substituted diheterocyclic compound is as shown in a formula (VI-1) or a formula (VI-2), and the synthesis route is as shown in the specification. The benzene-containing selenium group substituted diheterocyclic compound is good in monoamine oxidase inhibition activity and can be applied to preparation of a monoamine oxidase inhibitor. The formula (VI-1) and the formula (VI-2) are as shown in the specification.

Description

1. Technical field [0001] The invention relates to a biheterocyclic compound substituted with phenylselenyl group and its preparation and application, especially its application in the preparation of monoamine oxidase inhibitors. 2. Background technology [0002] The full name of monoamine oxidase (monoamine oxidase, MAO, EC1.4.3.4) is monoamine oxidoreductase, which was discovered by Balschko in the 1930s and is an enzyme that plays an important role in the metabolism of neurotransmitters. It catalyzes the oxidative deamination of amines produced by some organisms in the brain and peripheral nervous tissue to produce hydrogen peroxide. In 1968, Johnston divided monoamine oxidase into two subclasses, A and B, according to the sensitivity of monoamine oxidase to its irreversible inhibitor clorgyline (clorgyline). Monoamine oxidase A is sensitive to clorgyline, while monoamine oxidase B is insensitive. Further studies showed that monoamine oxidase A has high affinity for the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12A61K31/4245A61P25/00A61P25/24
CPCC07D417/14
Inventor 王宇光吴中礼朱冰春李清思张海梁
Owner ZHEJIANG UNIV OF TECH
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