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1,2-Dioxane[3,4-f]Nitrooxycyclononane Derivatives and Their Synthesis and Application

A synthetic method and alkyl technology, applied in the field of medicine, to achieve good anti-inflammatory activity, simple and easy-to-control synthetic method

Active Publication Date: 2021-08-03
南京搏克思新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, 1,2-dioxane[3,4-f]nitroxocyclononane derivatives have not been reported yet, so the study of its synthesis and application is of great significance for the discovery of new lead compounds

Method used

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  • 1,2-Dioxane[3,4-f]Nitrooxycyclononane Derivatives and Their Synthesis and Application
  • 1,2-Dioxane[3,4-f]Nitrooxycyclononane Derivatives and Their Synthesis and Application
  • 1,2-Dioxane[3,4-f]Nitrooxycyclononane Derivatives and Their Synthesis and Application

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Experimental program
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Effect test

Embodiment 1

[0041] The 1,2-dioxcyclohexene[3,4-f]nitroxycyclononane derivatives of the present invention were synthesized according to the following synthetic route.

[0042]

[0043] 3aa:R 1 =Ph,R 2 =Ph,R 3 =Me,R 4 =Me,R 5 = cinnamyl;

[0044] 3ba:R 1 = 4-OMeC 6 h 4 , R 2 = 4-OMeC 6 h 4 , R 3 =Me,R 4 =Me,R 5 = cinnamyl;

[0045] 3ca:R 1 = 4-CF 3 C 6 h 4 , R 2 = 4-OMeC 6 h 4 , R 3 =Me,R 4 =Me,R 5 = cinnamyl;

[0046] 3da:R 1 =3-BrC 6 h 4 , R 2 =3-BrC 6 h 4 , R 3 =Me,R 4 =Me,R 5 = styryl;

[0047] 3ea:R 1 =2-BrC 6 h 4 , R 2 =2-BrC 6 h 4 , R 3 =Me,R 4 =Me,R 5 = cinnamyl;

[0048] 3fa:R 1 =2-thienyl,R 2 =2-thienyl,R 3 =Me,R 4 =Me,R 5 = cinnamyl;

[0049] 3ga:R 1 =Ph, R 2 =Ph, R 3 =Et,R 4 =Et,R 5 = cinnamyl;

[0050] 3ha:R 1 =Ph,R 2 =Ph, R 3 =Ph, R 4 =Et,R 5 = cinnamyl;

[0051] 3ia:R 1 =Ph, R 2 =Ph, R 3 =-CH 2 -,R 4 =-(CH 2 ) 2 -,R 5 = cinnamyl;

[0052] 3ja:R 1 =Ph, R 2 =Ph, R 3 =-CH 2 -,R 4 =-(CH 2 ) 3 -,R 5 ...

Embodiment 2

[0081] The 1,2-dioxcyclohexene[3,4-f]nitroxycyclononane derivatives of the present invention were synthesized according to the following synthetic route.

[0082]

[0083] 3ab:R 5 = (α-Me)cinnamyl;

[0084] 3ac:R 5 = 3-Phenylpropargyl;

[0085] 3ad:R 5 =Et;

[0086] 3ae:R 5 =Bn;

[0087] 3af:R 5 =tBu.

[0088] To a dry glass vial equipped with a stir bar, add the corresponding N-alkenyl α,β-unsaturated nitrone 1 (0.2 mmol), scandium trifluoromethanesulfonate (Sc(OTf) 3 , 20mol%, 0.04mmol), eosin Y (Eosin Y, 20mol%) and 2mL organic solvent (wherein the organic solvent that target compound 3ab-3ae adopts is respectively acetone, trichloromethane, n-hexane and dioxane, target The organic solvent used in compound 3af is carbon tetrachloride), methylenecyclopropane 2 (0.4 mmol) was added into the vial, and the vial was sealed with plastic wrap. Then, the vial containing the mixture was stirred at room temperature and reacted under the irradiation of a white LED lamp (14W...

Embodiment 3

[0100] The 1,2-dioxcyclohexene[3,4-f]nitroxycyclononane derivatives of the present invention were synthesized according to the following synthetic route.

[0101]

[0102]3bf:R 1 =(4-OMe)C 6 h 5 , R 2 =(4-OMe)C 6 h 5 , R 3 =Me,R 4 =Me,R 5 =tBu;

[0103] 3hd:R 1 =Ph, R 2 =Ph, R 3 =Ph, R 4 =Et,R 5 =Et.

[0104] To a dry glass vial equipped with a stir bar was added the corresponding N-alkenyl α,β-unsaturated nitrone 1 (0.2 mmol), copper trifluoromethanesulfonate (Cu(OTf) 2 , 20mol%, 0.04mmol), Eosin Y (Eosin Y, 30mol%) and 2mL tert-butyl methyl ether, methylenecyclopropane 2 (0.4mmol) was added into the vial, and the vial was sealed with plastic wrap. Then, the reaction mixture was stirred at 40°C and irradiated under white LED lamp (17W) for 3-7 days until the complete consumption of nitrone N-alkenyl α,β-unsaturated 1 (monitored by TLC). At this time, the solvent was removed from the obtained reactant under reduced pressure, and the residue was separated by ...

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Abstract

The invention discloses a series of 1,2-dioxcyclohexene [3,4-f]nitrogenated cyclononane derivatives, their synthesis method and application. The 1,2-dioxane[3,4-f]nitroxycyclononane derivative of the present invention has the structure shown in the following formula (I), and its synthesis method mainly includes the following steps: take the following formula The compound shown in (II), the compound shown in formula (III), the photosensitizer and the catalyst are placed in an organic solvent, and react under light irradiation in the presence of oxygen to obtain the crude product of the target compound. The method of the invention is simple and easy to control, and some target compounds obtained have good anti-inflammatory activity and certain potential medicinal value. The compounds of structures shown in the formula (I), formula (II) and formula (III) are respectively as follows:

Description

technical field [0001] The invention relates to 1,2-dioxcyclohexene[3,4-f]nitroxocyclononane derivatives and a synthesis method and application thereof, belonging to the technical field of medicine. Background technique [0002] Organic peroxides are compounds in which peroxygen is bonded to carbon atoms. For a long time the greatest use of this class of compounds has been as free radical initiators. Until the 1970s, Chinese scientists discovered artemisinin, a natural product with excellent antimalarial activity, in which the peroxy bond in the molecule is the key to its antimalarial activity. Organic peroxides began to be highly valued by the medical and biological circles, and gradually aroused brand-new interest in the chemical circles. And the synthesis of this kind of peroxy compound, its key step and difficult point is exactly how to form or introduce peroxy bond. Natural sources of organic peroxides are limited and usually only small amounts of each compound can b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04A61K31/5365A61P29/00
CPCA61P29/00C07D498/04
Inventor 莫冬亮马小盼农彩梅徐佩佩苏桂发
Owner 南京搏克思新材料科技有限公司
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