5-phenyl isoxazole-containing stilbenoid compound and preparation method thereof

A technology for phenylisoxazole and compounds, which is applied in the field of compound preparation and can solve problems such as poor drug-like properties

Active Publication Date: 2016-11-16
东营睿港招商服务有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of compound has strong structural rigidity, poor drug-like properties, and the risk of hormone-like drugs

Method used

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  • 5-phenyl isoxazole-containing stilbenoid compound and preparation method thereof
  • 5-phenyl isoxazole-containing stilbenoid compound and preparation method thereof
  • 5-phenyl isoxazole-containing stilbenoid compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the synthesis of compound Ia (R=H)

[0015]

[0016] Compound II (1mmol), IIIa (R=H, 1mmol) and cesium carbonate (2mmol) were heated to 85°C in DMSO (5mL) solvent and kept at this temperature for 8 hours, and 20% hydrogen was added after reducing the reaction temperature to 60°C Potassium oxide solution (2 mL), reacted and stirred at 60° C. for 4 hours. Cool the reaction night to room temperature, acidify with hydrochloric acid and dilute with water to obtain a large amount of precipitate, filter and recrystallize with methanol to obtain compound Ia (R=H); Yellow solid; Yield: 42%; 1 H NMR (DMSO-d 6 ,400MHz)δ:13.15(brs,1H),8.12(s,1H),7.90(dd,J 1 =8.0Hz,J 2 =1.8Hz, 2H), 7.80(t, J=7.5Hz, 2H), 7.62(d, J=8.8Hz, 2H), 7.52~7.58(m, 3H), 7.47(t, J=7.7Hz, 1H ),7.29(d,J=16.4Hz,1H),7.22(d,J=16.4Hz,1H),7.20(s,1H),7.10(d,J=8.8Hz,2H),5.29(s,2H ); 13 CNMR (DMSO-d 6 ,100MHz)δ:170.0,168.2,161.8,158.1,138.0,131.1,130.8,130.3,129.8(2C),129.3,129.2,128.5(2C),128.4,1...

Embodiment 2

[0017] Embodiment 2: the synthesis of compound Ib (R=2-Cl)

[0018] Substitute IIIb (R=2-Cl) for IIIa (R=H), and obtain it by referring to the synthesis method of Ia in Example 1. Yellowsolid; Yield: 51%; 1 H NMR (DMSO-d 6 ,400MHz)δ:12.98(brs,1H),8.13(s,1H),7.82~7.88(m,2H),7.79(d,J=8.1Hz,1H),7.62(d,J=8.6Hz,2H ),7.49~7.54(m,1H),7.35(d,J=8.1Hz,2H),7.47(t,J=7.7Hz,1H),7.28(d,J=16.5Hz,1H),7.23(d ,J=16.5Hz,1H),7.10(d,J=8.6Hz,2H),7.09(s,1H),5.27(s,2H),2.37(s,3H);170.2,166.7,161.7,158.2, HRMS(ESI) calcd for C 25 h 17 ClNO 4 [M-H] - 430.0846, found 430.0831.

Embodiment 3

[0019] Embodiment 3: the synthesis of compound Ic (R=2-OMe)

[0020] Substitute IIIc (R=2-OMe) for IIIa (R=H), and obtain it by referring to the synthesis method of Ia in Example 1. Yellowsolid; Yield: 47%; 1 H NMR (DMSO-d 6 ,400MHz)δ:13.05(brs,1H),8.13(s,1H),7.79~7.83(m,2H),7.62(d,J=8.8Hz,2H),7.46~7.52(m,3H),7.26 (d, J=16.4Hz, 1H), 7.20(d, J=16.4Hz, 1H), 7.10~7.14(m, 2H), 6.99(s, 1H), 6.79(d, J=8.8Hz, 2H) ,5.29(s,2H),3.96(s,3H); 13 C NMR (DMSO-d 6 ,100MHz)δ:167.8,166.2,161.5,158.2,138.4,138.2,131.7,130.7,130.5,130.0,129.4,129.4,128.6(2C),128.2,127.4,127.2,126.1,124.6,121.6(2C) , 103.6, 61.8, 56.3; HRMS (ESI) calcd for C 26 h 20 NO 5 [M-H] - 426.1341, found 426.1376.

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Abstract

The invention relates to a 5-phenyl isoxazole-containing stilbenoid compound (I) and a preparation method thereof. The preparation method comprises the following steps: condensing methyl 4'-hydroxy stilbene-3-formate (II) and 5-phenyl-3-chloromethyl isoxazole (III), and further performing hydrolysis and acidification to obtain the 5-phenyl isoxazole-containing stilbenoid compound. The 5-phenyl isoxazole-containing stilbenoid compound I has inhibitory activity on protein tyrosine phosphatase-1B (PTP1B), and can be used for preparing hypoglycemic drugs.

Description

technical field [0001] The invention belongs to the field of compound preparation, and in particular relates to a 5-phenylisoxazole-containing scorpion compound and its preparation method and application. Background technique [0002] Diabetes is a serious threat to human health, and the number of patients is increasing year by year. So far there is no specific drug for the treatment of diabetes. Studies have shown that protein tyrosine phosphatase 1B (PTP1B) can down-regulate the expression of insulin, so inhibiting the activity of PTP1B is an effective means of treating diabetes by promoting insulin levels. [0003] Studies have shown that a variety of natural products including the steroid compound lithocholic acid (LCA) have good PTP1B inhibitory activity (IC 50 =12.7μM), the activity of the heterocyclic derivatives obtained by modifying the structure on PTP1B was significantly improved. However, this type of compound has strong structural rigidity, poor drug-like pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/08A61K31/42A61P3/10
CPCC07D261/08
Inventor 何海兵石玉军戴红李钰施磊李建华崔嵩
Owner 东营睿港招商服务有限责任公司
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