CN107721895B - Novel penta-substituted 2, 3-dihydropyrrole derivative and preparation method and application thereof - Google Patents
Novel penta-substituted 2, 3-dihydropyrrole derivative and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to a synthesis method of penta-substituted 2, 3-dihydropyrrole, which specifically comprises the steps of taking simple and easily obtained amine, aldehyde and α -ketoamide as raw materials, taking ethanol as a solvent, taking glacial acetic acid as a catalyst, and reacting at 60-80 ℃ to obtain a cis-dihydropyrrole compound.
Description
Technical Field
The invention belongs to the field of preparation methods and pharmaceutical applications of new compounds, and relates to a preparation method and applications of 2, 3-pyrroline compounds, including applications in antidiabetic drugs.
Technical Field
Dihydropyrroles are structural groups in many naturally occurring alkaloids and biologically active substances with a wide range of biological activities, such as, for example, gulconine, nicotine, tropine and cocaine. 2, 3-dihydropyrroles are reported to be important precursors for the synthesis of various natural products and other complex molecules. For example serotonin reuptake inhibitors from rituximab, Vildagliptin from Norwalk, Saxagliptin from BMS, Pirprofen, etc. Therefore, it is very important to develop an efficient method for constructing a dihydropyrrole skeleton.
The structures of dihydropyrrole and its derivatives are also difficult to find in many of the drug molecules already on the market. For example, atorvastatin calcium, a hypolipidemic drug manufactured by the company pfeiri, has a basic skeleton of pyrrole and is sold under the trade name lipitor for many years and is a top-grade worldwide drug. There is also the photodynamic therapy (PDT) second generation photosensitizer temoporfin, developed by Biolitec Pharma, uk, whose basic skeleton is dihydropyrrole, and is used clinically in advanced squamous carcinoma of the head and neck where radiotherapy, surgery and systemic chemotherapy are not appropriate.
Although many new synthetic methods for 2, 3-dihydropyrrole have been developed in the past decade, most of the known synthetic methods need to be carried out under the catalysis of transition metals or heavy metals, and easily cause environmental pollution, for example, the Hanbing Liang project group, which realizes the metal-alkene/Suzuki coupling reaction of acrylamide catalyzed by palladium, and constructs a multi-functional 2, 3-dihydropyrrole derivative, the Masahiro Yoshida project group reports the formation of 2-vinyl-2, 3-dihydropyrrole by the catalytic action of metal addition, cyclization elimination and the like by using β -enaminocarbonyl compound and 1, 4-diacetoxybut-2-ene under the catalytic action of metal palladium.
Disclosure of Invention
The invention aims to provide a method for synthesizing penta-substituted 2, 3-dihydropyrrole, which takes amine, aldehyde and α -ketoamide as raw materials, ethanol as a solvent and glacial acetic acid as a catalyst to react at 60-80 ℃ to generate 2, 3-dihydropyrrole compounds.
The purpose of the invention is realized by the following technical scheme:
the structure of the penta-substituted 2, 3-pyrroline compound has the following general formula:
wherein R is1Is substituted hydrogen, aryl or alkyl, R2Is a substituted aryl radical, R3Is a substituted aryl group.
The dihydropyrrole compound is obtained by the following synthetic route:
the solvent used for the reaction is ethanol. The reaction temperature is 60-80 ℃, and the reaction time is 6-12 hours.
The nomenclature and structure of the synthesized 2, 3-pyrrolines are shown in the following table:
TABLE 1 class of 2, 3-dihydropyrrole compounds
The invention has the advantages and positive effects that:
1. the invention adopts cheap and easily available amine, aldehyde and α -ketoamide as raw materials, and the reaction method has the obvious advantages of high stereoselectivity, wide substrate applicability, good atom economy and the like.
2. The reaction of the invention does not need anhydrous and anaerobic operation, has simple and convenient operation and is suitable for large-scale production and development.
3. The reaction of the invention does not need metal catalyst, adopts ethanol as solvent, has no environmental pollution, and accords with the concept of green chemistry.
4. The pyrroline compound has better inhibition activity on α -glucosidase.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of compound 4a in deuterated trichloromethane;
FIG. 2 is a nuclear magnetic carbon spectrum of compound 4a in deuterated trichloromethane;
FIG. 3 is a nuclear magnetic hydrogen spectrum of compound 4b in deuterated trichloromethane;
fig. 4 is a nuclear magnetic carbon spectrum of compound 4b in deuterated trichloromethane.
Detailed Description
For understanding the invention, the invention is further illustrated below with reference to examples of implementation: the following examples are illustrative and not limiting, and the scope of the invention is not to be limited by the following examples.
The following is a detailed description by way of example.
Example 1
Synthesis of Compound 4 a.
62mg (0.5mmol) of p-anisidine, 120mg (1.0mmol) of p-tolualdehyde and 200mg (1.0mmol) of p-chloropyruvic acid amide were placed in a 100ml round-bottomed flask and dissolved in 20ml of EtOH, and after stirring for 5 minutes, 1.6ml of acetic acid was added. The reaction flask was placed in an oil bath at 80 ℃ and heated under reflux for 8 hours. After cooling to room temperature, the ethanol was removed by concentration under reduced pressure and the residue was diluted with ethyl acetate and water. After separation, the aqueous phase was extracted twice more with ethyl acetate. The combined organic phases were successively saturated with KHSO4Aqueous solution, saturated NaHCO3Washing with saturated brine, anhydrous MgSO4Drying and vacuum concentratingAnd (5) condensing to obtain a crude product. Purification of PE/EA by silica gel column chromatography (5:1 to 3:1) gave 178mg of product 4a in 51% yield. Structural parameters are as follows:1H NMR(400MHz,CDCl3)δ8.90(s,1H),8.03(s,1H),7.20-7.15(m,6H),7.10(d,J＝8.4Hz,4H),7.03(d,J＝8.4Hz,2H),6.97(d,J＝8.0Hz,4H),6.86(d,J＝9.2Hz,2H),6.68(d,J＝8.8Hz,2H),5.11(s,1H),3.70(s,3H),2.22(s,3H),2.19(s,3H),1.67(s,3H).13C NMR(100MHz,CDCl3)δ184.4,168.3,166.3,162.4,158.3,140.5,137.3,135.8,135.6,134.2,130.8,129.6,129.33,129.26,129.21,129.1,128.84,128.77,128.69,128.3,128.0,121.6,121.1,114.4,111.0,78.6,61.0,55.4,23.5,21.5,21.1.HRMS(ESI-TOF)m/z calcd.forC41H36N3O4Cl2[M+H]+:704.2077,found 704.2052.
example 2
Synthesis of Compound 4 b.
The synthesis method of example 2 is the same as the general synthesis method described above.
Yield: 49 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)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).13CNMR(100MHz,CDCl3)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 C41H36N3O4Cl2[M+H]+:704.2077,found 704.2076.
example 3
Synthesis of Compound 4 c.
The synthesis method of example 3 is the same as the general synthesis method described above.
Yield: 62 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)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 C41H36N3O4Cl2[M+H]+:704.2077,found704.2079.
example 4
Synthesis of Compound 4 d.
The synthesis method of example 4 is the same as the above synthesis method.
Yield: 20 percent; structural parameters are as follows:1H NMR(400MHz,MeOD)δ7.32-7.28(m,4H),7.21-7.14(m,4H),7.12-7.07(m,3H),7.05-6.99(m,5H),6.93(d,J＝8.0Hz,2H),6.86(d,J＝8.0Hz,2H),6.70(d,J＝8.4Hz,2H),4.83(s,1H),3.64(s,3H),2.22(s,3H),2.04(s,3H),1.75(s,3H).HRMS(ESI-TOF)m/z calcd.for C41H38N3O4[M+H]+:636.2857,found 636.2840.
example 5
Synthesis of Compound 4 e.
The synthesis method of example 5 is the same as the general synthesis method described above.
Yield: 30 percent; structural parameters are as follows:1H NMR(400MHz,MeOD)δ7.32-7.26(m,4H),7.05(d,J＝10.0Hz,3H),7.01(d,J＝4.0Hz,2H),6.99(s,1H),6.89(d,J＝8.0Hz,2H),6.74(s,4H),6.72-6.70(m,4H),4.83(s,1H),3.73(s,3H),3.72(s,3H),3.66(s,3H),2.26(s,3H),2.09(s,3H),1.73(s,3H).HRMS(ESI-TOF)m/z calcd.for C43H42N3O6[M+H]+:696.3068,found696.3066.
example 6
Synthesis of Compound 4 f.
The synthesis method of example 6 is the same as the general synthesis method described above.
Yield: 25 percent; structural parameters are as follows:1H NMR(400MHz,CDCl3)δ8.49(d,J＝12.0Hz,1H),7.89(d,J＝7.6Hz,1H),7.22(d,J＝8.0Hz,2H),7.16(d,J＝8.0Hz,2H),7.11-7.03(m,6H),6.98(d,J＝7.6Hz,2H),6.93-6.87(m,6H),6.68(d,J＝8.8Hz,2H),5.20(s,1H),3.71(s,3H),2.29(s,3H),2.19(s,3H),1.69(s,3H).HRMS(ESI-TOF)m/z calcd.for C41H36N3O4F2[M+H]+:672.2668,found 672.2681.
example 7
Synthesis of 4g of Compound.
The synthesis method of example 7 is the same as the general synthesis method described above.
Yield: 23 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)δ8.45(s,1H),7.91(s,1H),7.22(d,J＝7.6Hz,2H),7.18(d,J＝7.6Hz,2H),7.07-6.97(m,12H),6.88(d,J＝8.8Hz,2H),6.66(d,J＝8.8Hz,2H),5.21(s,1H),3.70(s,3H),2.28(s,6H),2.26(s,3H),2.19(s,3H),1.68(s,3H).HRMS(ESI-TOF)m/z calcd.for C43H42N3O4[M+H]+:664.3170,found 664.3168.
example 8
Synthesis of Compound 4 j.
The synthesis method of example 8 is the same as the general synthesis method described above.
The yield is 37 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)δ7.36-7.35(m,4H),7.21(d,J＝8.4Hz,3H),7.17-7.11(m,5H),7.07(d,J＝8.4Hz,3H),7.03-6.94(m,6H),6.88(d,J＝8.8Hz,2H),6.75(d,J＝8.8Hz,2H),5.19(s,1H),4.94(s,2H),2.31(s,3H),2.20(s,3H),1.71(s,3H).HRMS(ESI-TOF)m/z calcd.for C47H40Cl2N3O4[M+H]+:780.2390,found780.2401.
example 9
Synthesis of Compound 4 k.
The synthesis of example 9 was performed as described above.
The yield is 26 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)δ8.60(s,1H),7.84(s,1H),7.48(d,J＝7.2Hz,2H),7.41-7.38(m,4H),7.34-7.30(m,1H),7.27(s,1H),7.25(s,1H),7.22(s,1H),7.18-7.13(m,5H),7.11-7.07(m,3H),7.03-6.97(m,7H),5.21(s,1H),2.30(s,3H),2.21(s,3H),1.77(s,3H).HRMS(ESI-TOF)m/z calcd.for C46H38Cl2N3O3[M+H]+:750.2285,found750.2258.
example 10
Synthesis of Compound 4 n.
The synthesis method of example 10 is the same as the above synthesis method.
Yield: 51 percent; structural parameters are as follows:1H NMR(400MHz,CDCl3)δ8.72(s,1H),7.46-7.38(m,2H),7.29(s,2H),7.15(d,J＝7.6Hz,2H),7.12-7.07(m,3H),7.04-6.97(m,5H),6.90(s,1H),6.83(d,J＝8.0Hz,1H),5.04(s,1H),3.25-3.18(m,1H),3.12-3.05(m,1H),2.43(s,3H),2.18(s,3H),1.88(s,3H),1.33-1.30(m,2H),1.01(sxt,J＝7.2Hz,2H),0.66(t,J＝7.2Hz,3H).HRMS(ESI-TOF)m/z calcd.for C38H37N3O3Cl2Na+[M+Na]+:676.2104,found 676.2092.
example 11
Synthesis of Compound 4 o.
The synthesis of example 11 was performed as described above.
Yield: 28%; structural parameters are as follows:1HNMR(400MHz,CDCl3)δ8.63(s,1H),7.29(s,1H),7.24-7.18(m,7H),7.11-7.05(m,4H),7.03-6.95(m,6H),6.66-6.59(m,3H),5.10(s,1H),4.57(d,J＝16.4Hz,1H),4.34(d,J＝16.0Hz,1H),2.37(s,3H),2.17(s,3H),1.79(s,3H).HRMS(ESI-TOF)m/z calcd.for C41H36N3O3Cl2[M+H]+:688.2128,found 688.2119.
example 12
Synthesis of Compound 4 p.
The synthesis method of example 12 is the same as the general synthesis method described above.
The yield is 34%; structural parameters are as follows:1H NMR(400MHz,CDCl3)δ9.22(s,1H),8.43(s,1H),7.47(s,1H),7.35-7.34(m,2H),7.21-7.17(m,3H),7.12-7.08(m,4H),6.99(d,J＝8.0Hz,1H),6.92(d,J＝7.6Hz,2H),6.87-6.83(m,4H),6.64(d,J＝8.4Hz,2H),6.53-6.49(m,1H),5.78(s,1H),3.91(s,3H),3.69(s,3H),3.65(s,3H),1.70(s,3H).HRMS(ESI-TOF)m/z calcd.forC41H36Cl2N3O6[M+H]+:736.1976,found 736.1986.
example 13
Synthesis of Compound 4 q.
The synthesis method of example 13 is the same as the general synthesis method described above.
Yield: 38 percent; structural parameters are as follows:1HNMR(400MHz,MeOD)δ7.90(s,1H),7.25(s,1H),7.18-7.13(m,4H),7.09-6.97(m,11H),6.72(d,J＝8.0Hz,3H),6.64(d,J＝7.6Hz,1H),4.84(s,1H),3.66(s,6H),3.53(s,3H),1.76(s,3H).HRMS(ESI-TOF)m/z calcd.for C41H36Cl2N3O6[M+H]+:736.1976,found 736.1974.
example 14
Synthesis of Compound 4 r.
The synthesis method of example 14 is the same as the above synthesis method.
Yield: 40 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)δ8.81(s,1H),8.14(s,1H),7.25-7.23(m,4H),7.21-7.17(m,2H),7.15-7.11(m,1H),7.09-7.05(m,2H),7.03-6.96(m,4H),6.86(d,J＝8.8Hz,2H),6.70-6.67(m,5H),5.06(s,1H),3.71(s,3H),3.68(s,3H),3.65(s,3H),1.65(s,3H).HRMS(ESI-TOF)m/z calcd.for C41H36Cl2N3O6[M+H]+:736.1976,found736.1956.
example 15
Synthesis of Compound 4 s.
The synthesis of example 15 was performed as described above.
Yield: 30 percent; structural parameters are as follows:1H NMR(400MHz,MeOD)δ7.47(d,J＝10.4Hz,2H),7.36-7.32(m,2H),7.29(s,1H),7.22-7.18(m,2H),7.17-7.13(m,2H),7.11-7.06(m,7H),7.04-6.98(m,2H),6.74(d,J＝8.8Hz,2H),4.86(s,1H),3.66(s,3H),1.80(s,3H).HRMS(ESI-TOF)m/zcalcd.for C39H30Cl4N3O4[M+H]+:744.0985,found 744.0984.
example 16
Synthesis of Compound 4 t.
The synthesis method of example 16 is the same as the general synthesis method described above.
Yield: 30 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)δ8.66(s,1H),7.57(s,1H),7.28-7.21(m,7H),7.17-7.13(m,5H),7.09-6.99(m,3H),6.88(d,J＝8.4Hz,3H),6.70(d,J＝8.4Hz,2H),5.23(s,1H),3.72(s,3H),1.72(s,3H).HRMS(ESI-TOF)m/z calcd.for C39H30Cl4N3O4[M+H]+:744.0985,found 744.0968.
example 17
Synthesis of Compound 4 u.
The synthesis of example 17 was performed as described above.
Yield: 32 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)δ8.65(s,1H),7.86(s,1H),7.36-7.35(m,6H),7.25-7.23(m,3H),7.18(d,J＝8.4Hz,2H),7.15-7.09(m,2H),7.05-6.97(m,4H),6.86(d,J＝8.4Hz,2H),6.77-6.69(m,6H),5.11(s,1H),4.95(s,2H),3.71(s,3H),3.65(s,3H),1.68(s,3H).HRMS(ESI-TOF)m/z calcd.for C47H39Cl2N3O6Na+[M+Na]+:834.2108,found834.2102.
example 18
Synthesis of compound 4 v.
The synthesis of example 18 was performed as described above.
Yield: 19 percent; structural parameters are as follows:1HNMR(400MHz,CDCl3)δ8.72(s,1H),8.49(s,1H),7.57-7.55(m,2H),7.32(s,1H),7.28-7.26(m,2H),7.23-7.18(m,3H),7.09-7.06(m,2H),6.99(d,J＝8.8Hz,2H),6.81(d,J＝8.8Hz,2H),6.38-6.37(m,1H),6.28-6.27(m,1H),6.21(s,2H),5.16(s,1H),3.78(s,3H),1.62(s,3H).HRMS(ESI-TOF)m/z calcd.for C35H28Cl2N3O6[M+H]+:656.1350,found 656.1348.
activity assay test for α -glucosidase inhibitory Activity
α -glucosidase product (Sigma, G5003) extracted from Saccharomyces cerevisiae was used as a target protein, 4-nitrobenzene- α -D glucopyranose-shake (pNGP, Sigma, N1377) was used as a substrate, a compound and acarbose were dissolved in DMSO, the enzyme and the substrate were dissolved in a phosphate buffer solution having a concentration of 0.05mol/L and a pH of 6.8, 20. mu.L of α -glucosidase (0.06U), 30. mu.L of the substrate (1mmol/L), 10. mu.L of a test compound, 140. mu.L of potassium phosphate buffer solution were incubated at 37 ℃ for 30 minutes in an enzymatic reaction system, and the enzyme activity was measured at a wavelength of 405nm with a microplate reader.
TABLE 1 penta-substituted 2, 3-dihydropyrroles compound α -glucosidase inhibiting activity
aIC of acarbose50The value is obtained.
Claims (2)
1. A novel penta-substituted 2, 3-dihydropyrrole derivative is characterized in that: the structure is as follows:
2. the use of the novel penta-substituted 2, 3-dihydropyrrole derivative according to claim 1 for the preparation of a medicament for the treatment of diabetes.
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