Selenium-containing benzobisfuran type compounds and preparation and applications thereof

The technology of benzobisfuran and compound is applied in the application field of preparing monoamine oxidase inhibitor, and can solve the problems of monoamine oxidase with single action effect and large toxic and side effects.

Active Publication Date: 2014-12-10
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

Method used

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  • Selenium-containing benzobisfuran type compounds and preparation and applications thereof
  • Selenium-containing benzobisfuran type compounds and preparation and applications thereof
  • Selenium-containing benzobisfuran type compounds and preparation and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Synthesis of benzobisfuran compound X-a-1

[0050]

[0051] (1) Put 0.513.5g of compound I (1.0mmol) into a round-bottomed flask equipped with a magnetic stirrer and a reflux condenser and dissolve it with 10mL of DMF, then add 0.346g (2.5mmol) of potassium carbonate, and react for ten minutes at room temperature Afterwards, (1.2mmol, 0.164g) bromoacetone was added, and the stirring reaction was continued for 5h. After TLC detected that the reaction was complete, 30 mL of dichloromethane was added, and then washed with a large amount of water (80 mL×5) until DMF was removed, the organic phase was separated, dried with anhydrous magnesium sulfate, concentrated, and subjected to thin-plate chromatography (E / P[ethyl acetate Esters: Petroleum ether] = 1:5.) The benzofuran compound II-1 was isolated with a yield of 80%.

[0052] (2) Dissolve the benzofuran compound II-1 (0.8mmol) obtained in step 1 in 15mL of toluene, and slowly add 0.146g (0.96mmol) of 1,8-dia...

Embodiment 2

[0054] Example 2 Synthesis of benzobisfuran compound X-a-2

[0055]

[0056] (1), drop 0.513.5g compound I (1.0mmol) into the round-bottomed flask equipped with magnetic stirrer, reflux condenser and dissolve it in 10mLDMF, add 0.276g (2.0mmol) potassium carbonate again, at room temperature After reacting for ten minutes, ethyl bromoacetate (1.5mmol, 0.251g) was added, and the stirring reaction was continued for 3.5h. After the reaction was complete as detected by TLC, the follow-up treatment was as in step 1 of Example 1, and a white solid benzofuran compound II-3 was isolated with a yield of 89%.

[0057] (2), the benzofuran compound II-3 (0.89mmol) obtained in step 1 was dissolved in 15mL of toluene, and the subsequent steps were as in example 1, step 2, to obtain the selenium-containing benzofuran compound X-a-2 with a yield of 78 %, the structure is characterized as follows:

[0058] 1 H NMR (400MHz, CDCl 3 )δ7.80-7.78(m,2H),7.63(s,1H),7.57-7.49(m,5H),7.47-7.41(m,5...

Embodiment 3

[0059] Example 3 Synthesis of benzobisfuran compound X-a-3

[0060]

[0061] (1), drop 0.513.5g compound I (1.0mmol) into the round-bottomed flask equipped with magnetic stirrer, reflux condenser and dissolve it in 10mLDMF, add (2.5mmol, 0.346g) potassium carbonate again, room temperature After reacting for ten minutes, 0.106 g (1.4 mmol) of acetonitrile was added, and the stirring reaction was continued for 6 h. After the reaction was detected by TLC, the follow-up treatment was as in step 1 of Example 1, and benzofuran compound II-3 was isolated with a yield of 75%.

[0062] (2), the benzofuran compound II-3 (0.75mmol) obtained in step 1 was dissolved in 15mL of toluene, and the subsequent steps were as in step 2 of Example 1 to obtain the selenium-containing benzofuran compound X-a-3 with a yield of 70 %, the structure is characterized as follows:

[0063] 1 H NMR (400MHz, CDCl 3 )δ7.89-7.68(m,7H),7.65(s,1H),7.64-7.49(m,5H),7.46-7.38(m,3H),5.19-5.13(m,1H),3.72-3.66( ...

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PUM

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Abstract

Selenium-containing benzobisfuran type compounds and preparation and applications thereof are disclosed. The structure formulas of the compounds are shown as a formula (X-a), a formula (X-b) and a formula (X-c), wherein R1 is a ketone group, an ester group or a cyano group, and R2 is C1-C6 alkyl, C1-C6 haloalkyl or aryl. A preparing route of the compounds is shown as follows. The compounds have good monoamine oxidase inhibitory activity and can be used for preparing monoamine oxidase inhibitors.

Description

technical field [0001] The invention relates to a selenium-containing benzobisfuran compound and its preparation and application, especially the application in the preparation of monoamine oxidase inhibitors. Background technique [0002] Benzofuran, also known as coumarone, oxyindene, and β-benzofuran, is an important class of natural organic compounds. Many natural products contain the structure of benzofuran, which is the core structure of a large number of natural products and drug candidates. , their multiple biological activities mainly include agonizing estrogen receptor β subtype (ERβ), antagonizing thyroxine receptor (THR) and H 3 They play an important role in the prevention and treatment of Alzheimer's disease, osteoporosis, cardiac arrhythmia, Parkinson's disease and tumors (Felder, C.C.et al.Journal of Pharmacology and Experimental Therapeutics, 1998, 284(1), 291-297; Twyman, L.J.et al.Tetrahedron Letters, 1999, 40(52), 9383-9384; Flynn, B.L.et al.Org.Lett., 20...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 王宇光朱冰春余丽华
Owner ZHEJIANG UNIV OF TECH
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