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Novel bromophenol amino thiourea compounds and preparation, drugs, and applications thereof

A technology of bromophenol thiosemicarbazide and bromophenol amino, which is applied in the fields of bromophenol thiosemicarbazide compounds I-IV and their pharmacological activities and pharmaceutical applications, can solve the problems such as no reports of bromophenol thiosemicarbazide compounds, and achieve normal cell Low toxicity, good antitumor activity and selective effect

Active Publication Date: 2017-05-31
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] The present invention couples the anti-tumor active group bromophenol and the thiosemicarbazide active group to design and synthesize the bromophenol thiosemicarbazide compound. In the prior art, there is no bromophenol thiosemicarbazide compound provided by the present invention and its drug as an active ingredient There are no reports of such derivatives or their pharmaceutical compositions used in the preparation or treatment of diseases such as tumors caused by various factors.

Method used

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  • Novel bromophenol amino thiourea compounds and preparation, drugs, and applications thereof
  • Novel bromophenol amino thiourea compounds and preparation, drugs, and applications thereof
  • Novel bromophenol amino thiourea compounds and preparation, drugs, and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: 2-(2,3-dibromo-4,5-dimethoxybenzylidene)thiosemicarbazide (2-(2,3-dibromo-4,5-dimethoxybenzylidene)hydrazinecarbothioamide, compound I ) preparation

[0026] Weigh 10mmol 2,3-dibromo-4,5-dimethoxybenzaldehyde (3.22g) and 11mmol thiosemicarbazide (1g) into a 500mL reaction flask, add 30mL ethanol (95%) and stir evenly, Add 5mL of glacial acetic acid dropwise, then reflux and stir at 65-70°C for about 10 hours, evaporate most of the ethanol under reduced pressure, add 20ml of ice water, filter to obtain a precipitate, wash the precipitate with ice water (30mL divided into three times), and recrystallize from ethanol to obtain 2-( 2,3-Dibromo-4,5-dimethoxybenzylidene)thiosemicarbazide, white solid, yield 96%; 1 H-NMR (500MHz, DMSO- d6 )δ: 11.62(1H,s), 8.44(1H,s), 8.34(1H,s), 8.20(1H,s), 7.80(1H,s), 3.91(3H,s), 3.76(3H,s ); 13 C-NMR (125MHz, DMSO- d6 )δ: 178.5, 153.0, 148.9, 142.1, 131.2, 121.6, 117.5, 110.6, 60.7, 57.1; ESIMS: m / z 393 [M-H] — HRESIMS: calc...

Embodiment 2

[0027]Example 2: 2-(2,3,6-tribromo-4,5-dimethoxybenzylidene)thiosemicarbazide (2-(2,3,6-tribromo-4,5-dimethoxybenzylidene) hydrazinecarbothioamide, compound II)

[0028] 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-dibromo-4,5-dimethoxybenzaldehyde is replaced by 2,3,6-tri Bromo-4,5-dimethoxybenzaldehyde, compound II was prepared as a white solid with a yield of 92%, 1 H-NMR (600MHz, DMSO- d6 )δ: 11.72(1H,s), 8.32(1H,s), 8.07(1H,s), 7.56(1H,s), 3.86(3H,s), 3.83(3H,s); 13 C-NMR (150MHz, DMSO- d6 )δ: 179.0, 152.5, 151.1, 141.8, 132.5, 122.0, 121.5, 119.5, 61.6, 61.5; ESIMS: m / z 471 [M-H] — HRESIMS: calcfor C10H10N3O2S Br3[M-H] — 471.7971, found 471.7960.

Embodiment 3

[0029] Example 3: 2-(2,3-dibromo-4,5-dihydroxybenzylidene)-N-phenylthiosemicarbazide (2-(2,3-dibromo-4,5-dihydroxybenzylidene)- N-phenylhydrazinecarbothi oamide, compound III)

[0030] The preparation method of compound III is similar to the preparation method of compound I, and its difference from Example 1 is that the raw material 2,3-dibromo-4,5-dimethoxybenzaldehyde is replaced by 2,3-dibromo- 4,5-dihydroxybenzaldehyde, compound III was prepared as a white solid with a yield of 78%, 1 H-NMR (600MHz, DMSO- d6 )δ: 11.94(1H,s), 10.16(2H,s), 10.03(1H,s), 8.50(1H,s), 7.73(1H,s), 7.60(2H,d,J=7.8Hz), 7.37(2H,dd,J=7.8,6.0Hz),7.19(1H,dd,J=7.2,7.2Hz); 13 C-NMR (150MHz, DMSO- d6 )δ: 176.4, 147.7, 145.9, 143.6, 128.7 (2C), 126.0, 125.8 (3C), 117.0, 113.8, 113.4; ESIMS: m / z 441 [M-H] — HRESIMS: calcfor C14H11N3O2SBr2[M-H] — 441.8866, found 441.8848.

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Abstract

The invention relates to bromophenol amino thiourea compounds (I-IV), and compositions and applications thereof, and also relates to a preparation method of the compounds. The chemical structure formula of the compounds is represented in the description. In the chemical structural formula, R1, R2, R3, R4, R5 and R6 are one or two of H, Br, OH, and OCH3. For the compound (I), R1 and R2 are Br; R3 and R4 are OCH3; and R5 and R6 are H. For the compound (II), R1 R2, and R5 are Br; R3 and R4 are OCH3; and R6 is H. For the compound (III), R1 and R2 are Br; R3 and R4 are OH; R5 is H; and R6 is phenyl. For the compound (IV), R1 and R2 are Br; R3 and R4 are OH; and R5 and R5 are H. The invention also relates to a composition containing at least one compound mentioned above or salts formed by a physiologically acceptable inorganic acid / organic acid and the compounds. The invention further relates to a dosage form of the composition, and the dosage form can be tablet, capsule, injection 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 thiosemicarbazide 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 gro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C337/08A61K31/175A61P35/00
CPCC07C337/08
Inventor 史大永王立军郭传龙江波王帅玉赵越
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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