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Novel five-substituted 2,3-dihydropyrrole derivative and preparation method and application thereof

A technology of dihydropyrrole and derivatives, which is applied in the application of antidiabetic drugs and the field of preparation of 2,3-dihydropyrrole compounds, can solve the problems of not being widely used, demanding reaction conditions, environmental pollution, etc., and achieves High stereoselectivity, good inhibitory activity, and good atom economy

Inactive Publication Date: 2018-02-23
TIANJIN UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires harsh reaction conditions and cannot be widely used.
In the past ten years, although many new synthesis methods of 2,3-dihydropyrrole have been developed, most of the known synthesis methods need to be carried out under the catalysis of transition metals or heavy metals, which are easy to cause pollution to the environment

Method used

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  • Novel five-substituted 2,3-dihydropyrrole derivative and preparation method and application thereof
  • Novel five-substituted 2,3-dihydropyrrole derivative and preparation method and application thereof
  • Novel five-substituted 2,3-dihydropyrrole derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of compound 4a.

[0031]

[0032] Take 62mg (0.5mmol) p-methoxyaniline, p-tolualdehyde 120mg (1.0mmol) and p-chloropyruvamide 200mg (1.0mmol) in a 100ml round bottom flask, and dissolve it with 20ml EtOH, stir for 5 After 1.6 ml acetic acid was added. The reaction bottle was placed in an 80°C oil bath and heated to reflux for 8 hours. After cooling to room temperature, it was concentrated under reduced pressure to remove ethanol, and the residue was diluted with ethyl acetate and water. After liquid separation, the aqueous phase was extracted two more times with ethyl acetate. The combined organic phases were successively washed with saturated KHSO 4 Aqueous solution, saturated NaHCO 3 Washed with aqueous solution and saturated brine, anhydrous MgSO 4 Dry and concentrate in vacuo to give crude product. PE / EA (5:1~3:1) was purified by silica gel column chromatography to obtain 178 mg of product 4a with a yield of 51%. Structural parameters: 1 H NMR (...

Embodiment 2

[0034] Synthesis of compound 4b.

[0035]

[0036] The synthetic method of embodiment 2 is the same as above-mentioned synthetic general method.

[0037] Yield: 49%; Structural parameters: 1 H NMR (400MHz, CDCl 3 )δ8.63(s,1H),7.79(s,1H),7.22-7.20(m,3H),7.18-7.13(m,4H),7.11-7.09(m,1H),7.05-6.95(m, 8H), 6.88(d, J=8.8Hz, 2H), 6.68(d, J=8.8Hz, 2H), 5.16(s, 1H), 3.71(s, 3H), 2.28(s, 3H), 2.20( s,3H),1.70(s,3H). 13 C NMR (100MHz, CDCl 3 )δ184.2,168.4,166.5,162.6,162.5,158.3,140.6,138.3,138.1,137.5,134.4,134.3,130.9,129.73,129.67,129.4,129.3,129.1,128.9,128.3,128.0,124.8,124.3,120.8,120.1 ,118.7,118.0,114.4,111.0,78.7,60.8,55.4,23.7,21.4,21.1.HRMS(ESI-TOF)m / z calcd.for C 41 h 36 N 3 o 4 Cl 2 [M+H] + :704.2077,found704.2076.

Embodiment 3

[0039] Synthesis of compound 4c.

[0040]

[0041] The synthetic method of embodiment 3 is the same as above-mentioned synthetic general method.

[0042] Yield: 62%; Structural parameters: 1 H NMR (400MHz, CDCl 3)δ8.93(s,1H),8.79(s,1H),7.70(dd,J=8.0,14.0Hz,2H),7.37-7.35(m,1H),7.32-7.29(m,2H),7.271 -7.269(m,1H),7.18(d,J=8.0Hz,2H),7.14-7.06(m,4H),7.02-6.97(m,1H),6.94(d,J=8.8Hz,3H), 6.90(d,J=7.6Hz,2H),6.66(d,J=8.8Hz,2H),5.28(s,1H),3.70(s,3H),2.28(s,3H),2.10(s,3H ),1.65(s,3H).HRMS(ESI-TOF)m / z calcd.for C 41 h 36 N 3 o 4 Cl 2 [M+H] + :704.2077,found704.2079.

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Abstract

The invention relates to a synthesis method of five-substituted 2,3-dihydropyrrole. The synthesis method comprises the specific steps that amine, aldehyde and alpha-keto-amide which are simple and areeasy to obtain are used as raw materials, an ethyl alcohol is used as a solvent and glacial acetic acid is used as a catalyst to perform reaction under the condition of 60-80 DEG C, and a cis-form dihydropyrrole compound is obtained. The method has the advantages that the method is simple and easy to operate, the reagents are cheap and easy to obtain, the atom economy is good, reaction stereoselectivity is high and the substrate applicability is good. In addition, the alpha-glucosidase inhibiting activity of the compound is evaluated for the first time, a result shows that the compound can very well inhibit alpha-glucosidase and is better than acarbose. The synthesis method has the wide prospect on the aspects of development and application of diabetes treating drugs.

Description

technical field [0001] The invention belongs to the field of preparation methods of new compounds and application of medicines, and relates to the preparation methods and applications of 2,3-dihydropyrrole compounds, including the application in antidiabetic drugs. technical background [0002] Dihydropyrrole is a structural group in many naturally occurring alkaloids and biologically active substances, which have a wide range of biological activities, such as coudine, nicotine, tropine and cocaine. 2,3-Dihydropyrrole has been reported to be an important precursor for the synthesis of various natural products and other complex molecules. For example, serotonin reuptake inhibitors from Eli Lilly, Vildagliptin from Novartis, Saxagliptin from BMS, Pirprofen, etc. Therefore, it is very important to develop efficient methods for constructing dihydropyrrole skeletons. [0003] It is not difficult to find the structures of dihydropyrrole and its derivatives in many marketed drug ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/22C07D405/14A61P3/10
CPCC07D207/22C07D405/14
Inventor 王栋郁彭德奥希里·洛朗李林娜孙华
Owner TIANJIN UNIV OF SCI & TECH
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