Bromophenol-oxazole compound and its use in drug for treatment on diabetes mellitus type 2

A technology for type 2 diabetes and oxazoles, which is applied to bromophenol-oxazole compounds and their application fields in medicines for the treatment of type 2 diabetes, and can solve the problems of low cell permeability and bioavailability, high hydrophilicity and electronegativity

Inactive Publication Date: 2017-04-26
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since most of these compounds contain phosphate or carboxylic acid groups, their high hydrophilicity and electronegativity lead to their cell permeability and bioavailability are too low

Method used

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  • Bromophenol-oxazole compound and its use in drug for treatment on diabetes mellitus type 2
  • Bromophenol-oxazole compound and its use in drug for treatment on diabetes mellitus type 2
  • Bromophenol-oxazole compound and its use in drug for treatment on diabetes mellitus type 2

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Synthesis and structural identification of 4-(5-(4-bromophenyl)oxazole-2-substituted)benzene-1,2-dihydroxy

[0021]

[0022] Add 15.2g of 4-hydroxy-3-methoxy-benzaldehyde into 50mL of dichloromethane, stir evenly, carefully add 20g of AlCl 3 . In an ice bath, slowly add 32 mL of pyridine in 10 mL of CH 2 Cl 2 solution. After dropping, reflux for 24 hours. Cool, add concentrated hydrochloric acid to adjust pH<3, separate the aqueous phase, extract with ethyl acetate, dry, and evaporate to dryness. The solid was recrystallized from water to obtain 3,4-dihydroxybenzaldehyde as a pale yellow solid with a melting point of 153-154°C.

[0023] Take 0.5mol of 1-(4-bromophenyl)ethanone and add 150mL of ethyl acetate and chloroform mixed solution, add 22.3g of CuBr under stirring 2 . Reflux for 2 hours, filter while hot, and wash with chloroform. The mixed solution was washed with water, dried, and evaporated to dryness to obtain a brown solid, which was 2-b...

Embodiment 2

[0026] Example 2: Synthesis and structure identification of 3,4-dibromo-5-(5-(4-phenoxyphenyl)oxazole-2-substituted)benzene-1,2-hydroxy

[0027]

[0028] Add 15.2g of 4-hydroxy-3-methoxy-benzaldehyde into 100mL of dichloromethane, and stir evenly. Under stirring at room temperature, a solution of 5.6 mL of bromine in 10 mL of methanol was added dropwise. React at room temperature for 2 hours, cool to 0°C, and add 50 mL of ice water dropwise. A precipitate was washed out, filtered, washed with ice water, and dried to obtain 21 g of white crystals. The resulting solid was added to 100 mL of acetic acid, and a solution of 5.6 mL of bromine in 15 mL of acetic acid was added dropwise. Add 0.1 g of reduced iron powder, and reflux for 2 hours. After cooling, filter, and recrystallize the solid from ethyl acetate to obtain 9.6 g of white needle crystals, which are 2,3-dibromo-4-hydroxy-5-methoxy-benzaldehyde. Add the resulting 2,3-dibromo-4-hydroxy-5-methoxy-benzaldehyde into 5...

Embodiment 3

[0032] Example 3: Synthesis and structural identification of 3-bromo-5-(5-(4-(4-chlorophenylthio)phenyl)oxazole-2-substituted)benzene-1,2-dihydroxy

[0033]

[0034] Add 15.2g of 4-hydroxy-3-methoxy-benzaldehyde into 100mL of dichloromethane, and stir evenly. Under stirring at room temperature, a solution of 5.6 mL of bromine in 10 mL of methanol was added dropwise. React at room temperature for 2 hours, cool to 0°C, and add 50 mL of ice water dropwise. A precipitate was washed out, filtered, washed with ice water, and dried to obtain 21 g of white crystals, which were 2-bromo-4-hydroxy-5-methoxy-benzaldehyde. Add the resulting 2-bromo-4-hydroxy-5-methoxy-benzaldehyde into 50 mL of dichloromethane, stir well, and carefully add 20 g of AlCl 3 . In an ice bath, slowly add 32 mL of pyridine in 10 mL of CH 2 Cl 2 solution. After dropping, reflux for 24 hours. Cool, add concentrated hydrochloric acid to adjust pH<3, separate the aqueous phase, extract with ethyl acetate, ...

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Abstract

The invention relates to a chemical total synthesis method of novel bromophenol-oxazole PTP1B and its use in a drug for treatment on diabetes mellitus type 2. The PTP1B inhibitor has a structural formula shown in the description. The compound improves insulin receptor sensibility through inhibiting the activity of protein tyrosine phosphatase 1B and has good treatment effects on insulin resistance-type diabetes mellitus type 2.

Description

technical field [0001] The invention relates to a new class of bromophenol-oxazole PTP1B inhibitors and its synthesis method, pharmacological activity and pharmaceutical use. The derivatives inhibit the activity of PTP1B, enhance the sensitivity of insulin receptors, make the physiological function of insulin normally play, and then regulate blood sugar, so as to achieve the therapeutic effect on insulin-resistant type 2 diabetes. Background technique [0002] Diabetes mellitus is a chronic metabolic disease caused by insufficient insulin secretion or decreased sensitivity of target tissues to insulin. According to data released by the World Health Organization (WHO) in November 2014, there are as many as 347 million diabetic patients worldwide. Diabetes is divided into insulin-dependent (type 1) and insulin-resistant (type 2), of which type 2 diabetes patients account for more than 90% of diabetes cases. Oral drugs currently on the market for the treatment of type 2 diabe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/32A61P3/10A61P5/50
CPCC07D263/32
Inventor 史大永李祥乾王立军江波
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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