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A kind of compound containing 5-phenylisoxazole group 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: 2019-12-17
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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  • A kind of compound containing 5-phenylisoxazole group and preparation method thereof
  • A kind of compound containing 5-phenylisoxazole group and preparation method thereof
  • A kind of compound containing 5-phenylisoxazole group and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Example 1: Synthesis of Compound Ia (R=H)

[0015]

[0016] Compound II (1 mmol), IIIa (R=H, 1 mmol) and cesium carbonate (2 mmol) were heated to 85 ℃ in DMSO (5 mL) solvent and kept at this temperature for 8 hours. After reducing the reaction temperature to 60 ℃, 20% hydrogen was added. Potassium oxide solution (2 mL), the reaction was stirred at 60°C for 4 hours. The reaction was cooled to room temperature overnight, acidified with hydrochloric acid and diluted with water to obtain a large amount of precipitate, which was filtered and purified by methanol recrystallization 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...

Embodiment 2

[0017] Example 2: Synthesis of Compound Ib (R=2-Cl)

[0018] Substitute IIIb (R=2-Cl) for IIIa (R=H), and obtain 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] Example 3: Synthesis of Compound Ic (R=2-OMe)

[0020] Substitute IIIc (R=2-OMe) for IIIa (R=H), and obtain by referring to the synthetic 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),128.2,127.4,127.2,126.1,124.6,121.3 , 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 compound containing a 5-phenylisoxazole group and a preparation method and application thereof. 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, thus 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 lithocholic acid (LCA), have good PTP1B inhibitory activity (IC 50 = 12.7 μM), the heterocycle-containing derivative obtained by modifying its structure significantly improved the activity of PTP1B. However, such compounds have strong structural rigidity, poor drug-like prope...

Claims

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Application Information

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Patent Type & Authority Patents(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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