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Aza11-membered ring compound, preparation method and application thereof, and medicine containing aza11-membered ring 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 relying on the inherent properties of special substrates and low synthesis yields, and achieve easy realization of reaction conditions, high yields, and expansion The effect of production

Active Publication Date: 2020-12-29
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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  • Aza11-membered ring compound, preparation method and application thereof, and medicine containing aza11-membered ring compound
  • Aza11-membered ring compound, preparation method and application thereof, and medicine containing aza11-membered ring compound
  • Aza11-membered ring compound, preparation method and application thereof, and medicine containing aza11-membered ring compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: An aza eleven-membered ring compound provided by the present invention has the following general structural formula:

[0036]

[0037] 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]azaundecane- 2,9(1H)-diketone, whose structural formula is:

[0038]

[0039] We define it as the basic body, the single crystal structure of the basic body is as figure 1 As shown, its molecular structure and other data are shown in the table below.

[0040]

[0041] The method for preparing described compound is, and the chemical reaction formula of this method is:

[0042]

[0043] Under the condition of argon, using toluene as solvent, toluene 1ml, firstly tris(dibenzylideneacetone)dipalladium-chloroform adduct (0.025eq) and (4,5-bis(diphenylphosphine)-9 , 9-dimethylxanthracene) phosphine ligand (0.01eq) coordination, stirring at room temperature, after the solution turns from r...

Embodiment 2

[0052] Embodiment 2: The aza eleven-membered ring compound disclosed by the present invention has the following general structural formula:

[0053]

[0054] 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-benzo[d][1,7]dioxa[3]nitrogen Heteroundecycyclo-2,9(1H)-dione, its structural formula is:

[0055]

[0056] The method for preparing the compound is the same as in Example 1, and the synthesis method for substrate 1 is the same as in Example 1.

[0057] Of course, in the specific synthesis, R 1 , R 2 , R 3 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.

[0058] The synthetic method of substrate 2 comprises the steps:

[0059] (1) Add (50-60ml) solvent (acetonitrile:water=4:1...

Embodiment 3

[0071] Embodiment 3: The aza eleven-membered ring compound disclosed by the present invention has the following general structural formula:

[0072]

[0073] R 1 May 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 ] Azaundecane-2,9(1H)-dione, its structural formula is:

[0074]

[0075] The method for preparing this compound is the same as Example one, the preparation method for substrate 1 is the same as Example one, the preparation method for substrate 2 is the same as Example two, and the R 1 The structure of the substituent, the recovery rate of the compound prepared by the method of the present invention is 82%, which is a semi-solid, and its proton nuclear magnetic spectrum, carbon spectrum and mass spectrum data are:

[0076] 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, 1H) ,6.82–6.72...

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Abstract

The invention discloses an aza 11-membered ring compound haveing the following structural general formula shown in the specification, and also provides a method for preparing the compound. The methodcomprises the following steps of: under the condition of argon, by taking methylbenzene as a solvent, coordinating a tri(dibenzylidene acetone)dipalladium-chloroform adduct with a (4,5-bis(diphenylphosphine)-9,9-dimethylxanthene)phosphine ligand; stirring, adding a substrate 1 and a substrate 2 after the solution turns yellow from red, and carrying out a reaction to obtain a final product 3 afterthe reaction is finished. The invention also discloses application of the compound and a medicine containing the compound. According to the invention, the exploration of the compound with the middle ring structure is further deeply carried out, the compound with the middle ring structure also has pharmaceutical activity, the preparation method capable of expanding production and large-scale production is provided, the adopted reaction substrate raw materials are very easy to obtain, the reaction conditions of the preparation method are easy to realize, the reaction time is shortened to the maximum extent, and high yield can be obtained.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to an aza eleven-membered ring compound, a preparation method and application thereof. Background technique [0002] The unique molecular framework constituted by the middle ring structure has always been a hotspot that chemists have paid close attention to. However, most of the biologically active mesolides only exist in natural products, and mesolides have multiple biological functions when there is a lactone group in them. Although their unique 3D structures can provide new references for non-pharmaceutical targets, these scaffolds are rarely found in the popular top 200 famous drugs and other approved active drugs. The main reason is that it is difficult to formulate an effective synthetic strategy and establish a variety of mesolide libraries for screening of medicinal materials. [0003] Conventional mesocyclic lactonization schemes are hampered by unf...

Claims

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Application Information

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Patent Type & Authority Applications(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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