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A kind of aza 11-membered ring compound and its preparation method, use and medicine containing the compound

A ring compound and compound technology, which is applied in the field of aza eleven-membered ring compounds and their preparation, can solve the problems of low synthesis yield and dependence on the inherent properties of special substrates, achieve high yield, and realize easy reaction conditions. The effect of expanding production

Active Publication Date: 2022-05-24
CHENGDU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these methods still rely heavily on the intrinsic properties of special substrates, and the overall synthetic yields are generally not high

Method used

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  • A kind of aza 11-membered ring compound and its preparation method, use and medicine containing the compound
  • A kind of aza 11-membered ring compound and its preparation method, use and medicine containing the compound
  • A kind of aza 11-membered ring compound and its preparation method, use and medicine containing the compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: a kind of aza 11-membered ring compound provided by the present invention, the compound has the following general structural formula:

[0035]

[0036] the R 1 for hydrogen, R 2 is methyl, R 3 When it is a benzene ring, (Z)-1-methyl-6-phenyl-4,7-dihydro-2H-benzo[d][1,7]dioxa[3]azaundecyl- 2,9(1H)-dione, its structural formula is:

[0037]

[0038] We define it as the basic body, the single crystal structure of the basic body is such as figure 1 The molecular structure and other data are shown in the table below.

[0039]

[0040] The method for preparing the compound is, the chemical reaction formula of the method is:

[0041]

[0042] Under argon, using toluene as solvent, 1ml of toluene, firstly, tris(dibenzylideneacetone)dipalladium-chloroform adduct (0.025eq) and (4,5-bis(diphenylphosphine)-9 ,9-dimethylxanthene) phosphine ligand (0.01eq) was coordinated, stirred at room temperature, after the solution changed from red to yellow, add ...

Embodiment 2

[0051] Embodiment 2: The aza 11-membered ring compound disclosed by the present invention has the following general structural formula:

[0052]

[0053] R 1 Can be a halogen substituent, R 2 is methyl, R 3 is a benzene ring, such as (Z)-1-methyl-6-phenyl-12-chloro-4,7-dihydro-2H-benzobenzo[d][1,7]dioxa[3]nitrogen Heteroundecacyclo-2,9(1H)-dione, its structural formula is:

[0054]

[0055] The method for preparing this compound is the same as that in Example 1, and the method for synthesizing substrate 1 is the same as that in Example 1.

[0056] Of course, in the specific synthesis, R 1 , R 2 , R 3 is consistent with the target product, although on the basis of the general structural formula, the R of each compound 1 , R 2 , R 3 They are different, but they are all synthesized according to the principle of the preparation method of the present invention.

[0057] The synthetic method of substrate 2 comprises the steps:

[0058] (1) Add (50-60ml) solvent (ace...

Embodiment 3

[0070] Embodiment 3: The aza 11-membered ring compound disclosed by the present invention has the following general structural formula:

[0071]

[0072] R 1 Can be a methoxy substituent, R 2 is methyl, R 3 is a benzene ring, for example, (Z)-1-methyl-6-phenyl-12-methoxy-4,7-dihydro-2H-benzo[d][1,7]dioxa[3 ] azaundecacyclo-2,9(1H)-dione, its structural formula is:

[0073]

[0074] The preparation method of this compound is the same as that of Example 1, the preparation method of Substrate 1 is the same as that of Example 1, and the preparation method of Substrate 2 is the same as that of Example 2. 1 The structure of the substituent group, the recovery rate of the compound prepared by the method of the present invention is 82%, and it is a semi-solid, and the data of its hydrogen nuclear magnetic spectrum, carbon spectrum and mass spectrum are:

[0075] 1 H NMR (600MHz, CDCl 3 )δ(ppm): 7.63(d, J=8.4Hz, 1H), 7.46(d, J=7.8Hz, 2H), 7.36(t, J=7.2Hz, 2H), 7.33–7.29(m, ...

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Abstract

The invention discloses an aza eleven-membered ring compound, which has the following general structural formula: The invention also provides a method for preparing the compound. Under the condition of argon, using toluene as a solvent, first tris(diethylene benzylacetone) dipalladium-chloroform adduct and (4,5-bis(diphenylphosphine)-9,9-dimethylxanthene) phosphine ligand coordination, after stirring, the solution turns from red to After it turns yellow, add substrate 1 and substrate 2 to react, and the final product 3 is obtained after the reaction is completed. The invention also discloses the application of the compound and the medicine containing the compound. Its advantages are: the exploration of the compounds with the middle ring structure is further deepened, and it is found that the compounds with the middle ring structure also have pharmaceutical activity, and a preparation method capable of expanding production and large-scale production is provided. The reaction conditions of the method are easy to realize, the reaction time is shortened to the greatest extent, and high yield can be obtained at the same time.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, in particular to an aza 11-membered ring compound and a preparation method and application thereof. Background technique [0002] The unique molecular skeleton formed by the middle ring structure has always been a hot spot for chemists. But at present, most of the mesocyclic lactones with biological activity only exist in natural products, and when there is a lactone group in the mesocyclic lactones, they have various biological functions. Although their unique 3D structures can provide new references for non-pharmaceutical targets, these scaffolds are rarely found in the popular top 200 well-known drugs and other approved active drugs. The main reason is that it is difficult to formulate effective synthetic strategies to establish a variety of mesocyclic lactone libraries for the screening of medicinal materials. [0003] The mid-ring structure is hindered by conventional mid-ring ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D273/01A61P35/00A61K31/395
CPCC07D273/01A61P35/00
Inventor 李俊龙戴青松陶应茂张翔冷海军向朋黄华李青竹刘悦漆婷黄茂林
Owner CHENGDU UNIV
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