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PTP1B (Protein Tyrosine Phosphatase 1B) inhibitor as well as chemical synthesis method and application thereof

A chemical synthesis and inhibitor technology, applied in the field of biomedicine, can solve the problems of poor selection specificity, not much, poor chemical and biological stability, etc., and achieve the effects of low-cost synthesis, simple process operation, and good industrial production prospects.

Inactive Publication Date: 2011-04-20
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are not many studies on PTP1B inhibitors in the world, mainly in the following categories: (1) Peptides: peptide substrates containing phosphorylated tyrosine residues (pTyr) have a higher affinity with PTP1B, But its chemical and biological stability are poor; (2), naphthoquinones Naphthnoquinone: inhibit the activity of enzyme by modifying the active site of PTPase; (3), thiazolidinediones Azolidinediones: increase the insulin sensitivity of target organ Improve blood sugar control, mainly including ciglitazone, troglitazone and rosiglitazone, but due to severe liver toxicity, ciglitazone has been withdrawn from the market; (4), Benzo[b]naphthol[2,3-d]furans and thiophenes: benzbromarone (PTP1B inhibitor, IC 50 =26μM) as the lead compound designed and synthesized as a series of Benzo[b]naphthol[2,3-d]furans and thiophenes compounds, which showed good hypoglycemic activity in mice, but it still needs to be used as a drug for treating diabetes. Overcoming many obstacles, such as high electronegativity, poor cell membrane permeability, and poor selective specificity, all of which make these inhibitors less druggable

Method used

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  • PTP1B (Protein Tyrosine Phosphatase 1B) inhibitor as well as chemical synthesis method and application thereof
  • PTP1B (Protein Tyrosine Phosphatase 1B) inhibitor as well as chemical synthesis method and application thereof
  • PTP1B (Protein Tyrosine Phosphatase 1B) inhibitor as well as chemical synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 "(2', 3'-dibromo-4', 5'-dimethoxy-phenyl)-(2,3,6-tribromo-4,5-dimethoxy-phenyl )-Methanone"Chemical Total Synthesis and Structure Identification

[0031] (1) Chemical synthesis and structure identification of Bis-(3,4-dimethoxy-phenyl)-methanone 3

[0032] Add 22.08g (120mmol) veratrol (compound 1), 16.92g (120mmol) veratrol (compound 2) and 100g polyphosphoric acid into a 250ml three-necked reaction flask according to the molar ratio of 1:1, and stir at 80°C for reaction 1h; cool to 60°C and add 250ml of ice water dropwise to the reactant within 30min, at this time, a large amount of water-insoluble pink solid precipitates out of the reactant; after removing water by filtration, dissolve the obtained solid in 100ml of dichloromethane , washed three times with an equal volume of 3% sodium hydroxide solution and distilled water successively; after drying the dichloromethane phase with anhydrous sodium sulfate, concentrate under reduced pressure to obtain a pin...

Embodiment 2

[0040] Example 2 Determination of protein tyrosine phospholipase 1B inhibitory activity

[0041] Compounds 3, 4, 5 and 6 to be tested were prepared into different concentrations of the test solution with DMSO, and 2 μL of the test solution was added to the standard bioassay system (50mM Tris-HCl, pH 6.5, 2mM pNPP , 2% DMSO, 30nM hGST-PTP1B), negative control: DMSO, positive control: sodium orthovanadate, the reaction temperature is 30°C, the dynamic measurement wavelength is the light absorption at 405nm, the time is 3min, and the compound PTP1B enzyme is calculated according to the following formula Vitality inhibition rate. Inhibition rate=(experimental group A value-negative control group A value) / (control group A value-negative control group A)×100%, the results are shown in Table 1.

[0042] Table 1 Inhibition rate of protein tyrosine phospholipase 1B (%)

[0043] Table 1 Inhibitory Ratio(%) of PTP1B

[0044]

[0045] When the compound concentration is 20 μg...

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Abstract

The invention relates to a PTP1B (Protein Tyrosine Phosphatase 1B) inhibitor as well as a chemical synthesis method and application thereof. The chemical structural formula of the PTP1B inhibitor is shown as the description, wherein the group connected with 2,2',3,3',6-position carbon of benzene ring is a bromine atom; 4,4',5,5'-position carbon is connected with methoxy; and the chemical name of the PTP1B inhibitor is (2',3'-dibromo-4',5'-dimethoxy-phenyl)-(2,3,6-tribromo-4,5-dimethoxy-phenyl)-ketone. Through inhibiting the PTP1B activity and increasing the susceptibility of an insulin receptor, the compound has favorable therapeutical effect on insulin resistance type 2 diabete.

Description

technical field [0001] The present invention relates to biomedicine, specifically a brominated compound "(2', 3'-dibromo-4', 5'-dimethoxy-phenyl)-(2,3,6-tribromo -4,5-dimethoxy-phenyl)-methanone" and its chemical total synthesis method, pharmacological activity and pharmaceutical use. As an insulin sensitizer, the compound and its derivatives can be used for treating insulin-resistant type 2 diabetes. Background technique [0002] Diabetes (Diabetes Mellitus, DM) is a chronic endocrine and metabolic disease. Currently, the drugs used to treat type 2 diabetes (Type 2 Diabetes Mellitus, T2DM) mainly include biguanides, sulfonylureas, α-glucosidase inhibitors and thiazolidine diuretics. Ketones, etc., have various disadvantages because they are mostly designed for symptoms rather than molecular target drugs for etiology. Therefore, the market is in urgent need of safe, effective, reasonably priced and long-term safe hypoglycemic drugs. [0003] Insulin resistance is a key fac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/63A61K31/12A61P3/10
Inventor 史大永范晓李敬郭书举
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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