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Biphenyl methylene-2-sulpho-4-thiazolone compound as well as preparation method and application thereof

A technology of biphenylmethylene and benzylidene, which is applied in the fields of medicinal chemistry and pharmacotherapeutics, can solve the problems of impaired insulin signaling in insulin resistance and increased catalytic activity of PTP1B dephosphorylation.

Inactive Publication Date: 2012-07-11
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above research results confirm that PTP1B plays a negative regulatory role in insulin signal transduction, and its overexpression will increase the catalytic activity of PTP1B dephosphorylation, which will lead to insulin resistance and impaired insulin signal transduction, which is the cause of type II diabetes and diabetes. Major Factors of Obesity

Method used

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  • Biphenyl methylene-2-sulpho-4-thiazolone compound as well as preparation method and application thereof
  • Biphenyl methylene-2-sulpho-4-thiazolone compound as well as preparation method and application thereof
  • Biphenyl methylene-2-sulpho-4-thiazolone compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1: 5-[3-(3-benzylaminophenyl)benzylidene]-2-thio-4-thiazolone (compound 1-a)

[0067]

[0068] Referring to the preparation process of the aforementioned compound x-a, compound 1-a was prepared:

[0069] a) Dissolve 375mg (2mmol) of compound 1 (3-bromoaniline) in 10mL of 1,2-dichloroethane, add 0.897g (4.5mmol) of benzaldehyde, 0.25mL (4.5mmol) of ice Acetic acid and 1.48g (7.0mmol) sodium triacetate borohydride, the mixed solution was stirred overnight at room temperature under nitrogen protection. After TLC detected that the reaction was complete, the reaction solution was diluted with 30 mL of 1,2-dichloroethane, and then washed with water (20 mL), saturated sodium bicarbonate (15 mL) and saturated brine (15 mL) successively, and the organic phase was washed with anhydrous sodium sulfate After drying, the organic solvent was distilled off under reduced pressure. The obtained white solid was 303 mg, yield: 75.4%. It was directly used in the next reaction...

Embodiment 2

[0077] Example 2: 5-[3-(4-benzylaminophenyl)benzylidene]-2-thio-4-thiazolone (compound 3-a)

[0078] The operation was the same as in Example 1, except that 4-bromoaniline was used instead of 3-bromoaniline to obtain 34.6 mg of a yellow solid, namely compound 3-a, with a yield of 85.9%.

[0079] 1 H NMR (300MHz, DMSO-d 6 )δ7.76-7.59(m, 5H), 7.46(d, J=9.2Hz, 2H), 7.38-7.21(m.5H), 7.05(d, J=10.4Hz, 1H), 4.51(s, 2H )

[0080] ESI-MS: m / z 403.0 (M+1, 100%)

Embodiment 3

[0081] Example 3: 5-[3'-[3-(1-benzylpiperidine-4-amino)phenyl]benzylidene]-2-thio-4-thiazolone (compound 1-b)

[0082]

[0083] Referring to the preparation process of the aforementioned compound x-b, compound 1-b was prepared:

[0084] a) In a 25mL round bottom flask, under argon protection, 136mg (1.0mmoL) of compound B-1, 207mg (1.5mmoL) of potassium carbonate, 202mg (1.2mmoL) of benzyl bromide were dissolved in 15mL of acetone, Then continue to add catalytic amount of potassium iodide, and the whole reaction system was refluxed for 6 hours. After the completion of the reaction as detected by TLC, the reaction system was cooled to room temperature, potassium carbonate was removed by filtration, and the organic solvent was evaporated under reduced pressure. 163 mg of a yellow oil was obtained, that is, compound B-2, yield: 86.2%. It was directly used in the next reaction without purification.

[0085] b) 171mg (1mmol) of 3-bromoaniline was dissolved in 10mL of 1,2-dich...

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Abstract

The invention relates to a biphenyl methylene-2-sulpho-4-thiazolone compound with a structure shown in the general formula (I), and a preparation method and application of the compound, as well as a medicine composition containing the compound. A biological activity test proves that the compound can obviously inhibit the activity of protein tyrosine phosphatase (PTP)-1B. Therefore, the biphenyl methylene-2-sulpho-4-thiazolone compound disclosed by the invention can be used as an inhibitor for the PTP-1B for preventing or symptomatically treating diabetes mellitus or adiposis.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to biphenylmethylene-2-thio-4-thiazolone compounds and their preparation methods, and the use of such compounds in the preparation of medicines for treating diabetes and obesity application. Background technique [0002] Diabetes is a chronic metabolic disorder caused by environmental factors and genetic factors. It is characterized by high blood sugar. There is a certain concentration of glucose in the normal human body, which provides energy for human life activities. After the human body eats, the blood sugar concentration will rise. Under the action of insulin, the glucose in the human blood enters the cells, and through a series of biochemical reactions, it provides the energy needed for daily activities. When the human body lacks insulin or target tissue cells (such as skeletal muscle cells, adipose tissue cells, etc.) are less sensitive to insul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/36C07D417/12A61K31/454A61K31/426A61P3/10A61P3/04
Inventor 沈竞康李佳张豹子孟韬马兰萍王昕姜如炜
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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