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Novel bromophenol-thiazole compounds as well as preparation, pharmaceutical and use thereof

A technology of compounds and thiazoles, applied in the fields of bromophenol-thiazole compounds I-IV and their pharmacological activities and pharmaceutical applications, can solve the problems of no reports of bromophenol-thiazole hybrid compounds, achieve good anti-tumor activity, good Application prospect, effect of strong inhibitory activity

Inactive Publication Date: 2017-05-31
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention utilizes the principle of drug molecular hybrid design to couple bromophenol and thiazole compounds with anti-tumor active groups to design and synthesize bromophenol-thiazole compounds. There is no bromophenol-thiazole hybrid compound provided by the present invention in the prior art and its pharmaceutical composition as an active ingredient, and there are no reports of such derivatives or their pharmaceutical composition being used in the preparation or treatment of diseases such as tumors or cancers caused by various factors.

Method used

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  • Novel bromophenol-thiazole compounds as well as preparation, pharmaceutical and use thereof
  • Novel bromophenol-thiazole compounds as well as preparation, pharmaceutical and use thereof
  • Novel bromophenol-thiazole compounds as well as preparation, pharmaceutical and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: 2-(2-(3-bromo-4,5 dimethoxybenzylidene)hydrazino)-4-(3,4-difluorophenyl)thiazole (2-(2-( 3-bromo-4,5-dimethoxybenzylidene)hydrazinyl)-4-(3,4-difluorophenyl)thiazole, compound I);

[0028] (1) Weigh 50mmol of 3-bromo-4,5 dimethoxybenzaldehyde (12.2g) and 55mmol of thiosemicarbazide (5g) into a 100mL reaction flask, add 50mL of ethanol (95%) and stir evenly, drop 2.5 mL of glacial acetic acid, then reflux and stir at 65-70 ° C for about 8 hours, evaporate most of the ethanol under reduced pressure, add 20 mL of water, filter to obtain a precipitate, wash the precipitate with water (30 mL for three times), and recrystallize from ethanol to obtain the intermediate 3-bromo- 4,5 Dimethoxybenzylidene Thiosemicarbazide.

[0029] (2) Weigh 1 mmol of intermediate 3-bromo-4,5 dimethoxybenzylidene thiosemicarbazide (317 mg) and 4 mmol of anhydrous sodium acetate into a 100 mL reaction flask, add 20 mL of absolute ethanol, and then add 1mmol 3′,4′-difluoro-2-bromoacetop...

Embodiment 2

[0030] Example 2: 2-(2-(3-bromo-4,5 dimethoxybenzylidene)hydrazino)-4-(4-trifluoromethyl)phenyl)thiazole (2-(2- (3-bromo-4,5-dimethoxybenzylidene)hydrazinyl)-4-(4-(trifluoromethyl)phenyl)thiazole, compound II)

[0031] The preparation method of compound II is similar to the preparation method of compound I, and its difference from Example 1 is that the raw material 2,3',4'-difluoro-2-bromoacetophenone is replaced by 4'-trifluoromethyl -2-Bromoacetophenone, compound II was prepared, gray solid, yield 91%,

[0032] 1 H-NMR (500MHz, DMSO- d6 )δ:12.31(1H,s),8.04(2H,d,J=8.0Hz),7.95(1H,s),7.73(2H,d,J=8.0Hz),7.54(1H,s),7.44( 1H,s),7.31(1H,s),3.86(3H,s),3.74(3H,s); 13 C-NMR (125MHz, DMSO- d6 )δ: 168.8, 154.0, 149.5, 146.8, 140.1, 138.8, 132.3, 127.9, 126.5(2C), 126.0(2C), 125.9, 122.2, 117.8, 110.4, 107.0, 60.6, 56.5; ESIMS: m / z 486[ M+H] + HRESIMS: calc for C 19 h 15 N 3 o 2 f 3 SBr[M+H] + 486.0140,found 486.0079.

Embodiment 3

[0033] Example 3: 2-(2-(2,3-dibromo-4,5 dimethoxybenzylidene)hydrazino)-4-(3,4-difluorophenyl)thiazole (2-( 2-(2,3-dibromo-4,5-dimethoxybenzylidene)hydrazinyl)-4-(3,4-difluorophenyl)thiazole, compound III)

[0034] The preparation method of compound III is similar to the preparation method of compound I, the intermediate 2,3-dibromo-4,5 dimethoxybenzylidene thiosemicarbazide is prepared first, and then the raw material 3',4'-difluoro -2-Bromoacetophenone was reacted to obtain compound III, a gray solid, with a yield of 87%, 1 H-NMR (500MHz, DMSO- d6 )δ:8.32(1H,s),7.81(1H,m),7.66(1H,s),7.49(1H,s),7.39-7.45(2H,overlap),3.88(3H,s),3.76(3H ,s); 13 C-NMR (125MHz, DMSO- d6 )δ: 168.7, 152.8, 150.6, 148.8, 148.6, 148.3, 140.4, 132.7, 131.4, 122.6, 121.7, 118.1, 116.3, 114.7, 109.1, 105.6, 60.7, 56.5; ESIMS: m / z 531 [M+H] + HRESIMS: calc for C 18 h 13 N 3 o 2 f 2 SBr 2 [M+H] + 531.9136,found 531.9130.

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Abstract

The invention relates to preparation of novel bromophenol-thiazole compounds I-IV, combination of the novel bromophenol-thiazole compounds, and application of the novel bromophenol-thiazole compounds in anti-tumor and / or anti-cancer pharmaceuticals. The invention also relates to a preparation method of the compounds, wherein chemical structures of the compounds have a general formula as follows: (shown in the figure), R1, R2 and R3 in the general formula are respectively selected from one of H, F, CF3 and Br, wherein R3 in the compound I is H, R1 and R2 are F; R1 in the compound II is H, R2 is CF3 and R3 is H; R3 in the compound III is Br, R1 and R2 are F; R1 and R2 in the compound IV are H, and R3 is Br. The invention further relates to salt formed by at least one of the compounds or physiologically acceptable inorganic acid or organic acid thereof, if appropriate, a pharmaceutically acceptable excipient and / or diluent or excipient; the invention further relates to an administering dosage form containing at least one of the compounds or the salt thereof, wherein the dosage form is tablet, capsule, infusion solution, suppository, patch, powder, suspension and the like.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a class of bromophenol-thiazole compounds I-IV and their pharmacological activity and pharmaceutical use. The compound and its derivatives can be used to prevent and / or treat diseases such as tumors or cancers caused by various factors. Background technique [0002] Malignant tumors seriously affect people's health and have become the second leading cause of human death, second only to cardiovascular and cerebrovascular diseases. According to the statistics of the World Health Organization, more than 10 million cancer patients are newly diagnosed every year in the world, and the total number of cancer deaths worldwide reaches 7 million people every year. With the aggravation of environmental pollution, the incidence of cancer is increasing year by year, showing a trend of multiple occurrences. The WHO 2014 report predicts that global cancer cases will show a rapid growth trend...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/50A61K31/426A61P35/00
CPCC07D277/50
Inventor 史大永王立军郭传龙江波赵越
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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