Flavonoid imidazole compounds and preparation method thereof

A technology of flavonoid imidazoles and compounds, applied in the field of organic drug synthesis, to achieve the effects of easy-to-obtain raw materials, simple preparation methods, and short synthetic routes

Inactive Publication Date: 2020-03-17
YANCHENG TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the development of flavonoid imidazole derivatives is still in the research stage

Method used

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  • Flavonoid imidazole compounds and preparation method thereof
  • Flavonoid imidazole compounds and preparation method thereof
  • Flavonoid imidazole compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1, the preparation of compound IV-1

[0035]

[0036] According to literature method steps, weigh resorcinol (4.37g, 39.7mmol), ZnCl 2 (0.54g, 39.7mmol), chloroacetonitrile (2.5mL, 39.7mmol) were placed in a three-necked flask, dissolved with ether solution, in an ice-water bath, fed with HCl gas for 4 hours and left to stand overnight, the next day HCl gas was bubbled again for 1 hour, and the white precipitated solid was filtered off. The obtained white solid was then refluxed in 1 mol / L hydrochloric acid solution for 1 hour, cooled in an ice-water bath to condense a large amount of white cotton flocculent solid, filtered by suction and dried to obtain 6.83 g of compound IV-1. Light pink powdery solid with a melting point of 130-132°C and a yield of 92.5%.

Embodiment 2

[0037] Embodiment 2, the preparation of compound I-1

[0038]

[0039] Add 10% NaOH (7mL) dropwise to a 100mL round bottom flask containing compound IV-1 (0.93g, 5.0mmol), 2-imidazolaldehyde (0.48g, 5.0mmol) and an appropriate amount of ethanol (15mL), and stir at room temperature After 24 hours of reaction, TLC traced until the reaction was completed, neutralized it to pH = 7 with 1 mol / L dilute hydrochloric acid, recrystallized and dried to obtain 0.98 g of compound I-1 with a yield of 86.9%.

[0040] Compound I-1: yellow powder; melting point 157-158°C; 1 H NMR (400MHz, DMSO-d 6 ) δ:12.39(s,1H,OH),7.61(d,J=8.4Hz,1H,flavone-5-H),7.33(m,2H,imidazole-4,5-2H),6.79(s,1H , flavone-3-H), 6.71 (d, J=8.4Hz, 1H, flavone-6-H), 6.60 (s, 1H, flavone-8-H) ppm.

Embodiment 3

[0041] Embodiment 3, the preparation of compound 1-2

[0042]

[0043] Add 10% NaOH dropwise to a 100mL round bottom flask containing compound IV-1 (0.93g, 5.0mmol), N-n-propyl-2-imidazolaldehyde (0.69g, 5.0mmol) and an appropriate amount of ethanol (15mL). (7 mL), stirred and reacted at room temperature for 24 hours, followed by thin-layer chromatography until the end of the reaction, neutralized to pH=7 with 1mol / L dilute hydrochloric acid, and then obtained 1.11g of compound I-2 after recrystallization and drying. was 82.7%.

[0044] Compound I-2: yellow powder; melting point 161-162°C; 1 H NMR (400MHz, DMSO-d 6 ) δ: 7.61(d, J=8.5Hz, 1H, flavone-5-H), 7.43(d, J=0.9Hz, 1H, imidazole-4-H), 7.22(d, J=0.7Hz, 1H, imidazole-5-H),6.78–6.63(m,3H,flavone-3-H, flavone-6-H,flavone-8-H),4.15(t,J=7.1Hz,2H,imidazole-CH 2 ), 1.72 (dd, J = 14.4, 7.3Hz, 2H, CH 2 ), 0.85(t, J=7.4Hz, 3H, CH 3 ) ppm.

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Abstract

The invention provides a flavone imidazole compound or pharmacologically acceptable salt thereof. General formula of the flavone imidazole compound is a general formula I, a general formula II or a general formula III, wherein R1 is selected from hydrogen, alkyl or hydroxy; R2 is selected from hydrogen, alkyl or hydroxyl; R3 is selected from hydrogen, alkyl or hydroxyl; R4 is selected from hydrogen, alkyl and substituted aryl; R5 is selected from hydrogen or normal-butyl; R6 is selected from hydrogen or chlorine. The invention also provides a preparation method of the flavone imidazole compound. After indicating by active detection results of in-vitro PTP1B (protein-tyrosine-phosphatase 1B), the synthesized flavone imidazole compound has certain inhibiting action on PTP1B; the basic theoretical basis is provided for developing of Type 2 diabetic mellitus drugs using the PTP1B as a target. The flavone imidazole compound has the advantages that the synthesizing route is short, the preparation method is simple, the obtaining of raw materials is easy, and the cost is low; the flavone imidazole compound is expected to provide more efficient and safe candidate drugs for treating the Type 2 diabetic mellitus, and is favorable for solving the problem of clinical treatment.

Description

technical field [0001] The invention relates to the field of organic drug synthesis, in particular to a class of flavonoid imidazole compounds, or pharmaceutically acceptable salts of such compounds, and a preparation method thereof. Background technique [0002] Flavonoids (also known as flavonoids) are important natural organic compounds with broad-spectrum physiological and pharmacological activities, low toxicity and strong biological activity. plant. However, natural flavonoids have a complex structure, poor solubility, and low utilization rate of physiological activity, which limits their wide clinical application. Therefore, scientific researchers focus on structural modification of flavonoids, on the one hand, to enhance their solubility and bioavailability; on the other hand. On the one hand, strive to develop new flavonoid compounds with stronger activity and less toxic side effects. [0003] Protein tyrosine phosphatase 1B (PTP1B) is an important intracellular r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04A61P3/10
CPCC07D405/04
Inventor 张玲宋浩明张欢吴晓昱查晶健
Owner YANCHENG TEACHERS UNIV
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