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N'-arylmethylene-2-(4-oxothiophene[2,3-d]pyrimidin-3-yl)acetyl hydrazone compounds, and preparation method and application thereof

An aryl methylene, 3-d technology, applied in the field of medicinal chemistry and pharmacotherapeutics, can solve the problem of incomplete understanding of cell apoptosis

Inactive Publication Date: 2012-02-01
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But strictly speaking, the exact mechanism of apoptosis is still not fully understood

Method used

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  • N'-arylmethylene-2-(4-oxothiophene[2,3-d]pyrimidin-3-yl)acetyl hydrazone compounds, and preparation method and application thereof
  • N'-arylmethylene-2-(4-oxothiophene[2,3-d]pyrimidin-3-yl)acetyl hydrazone compounds, and preparation method and application thereof
  • N'-arylmethylene-2-(4-oxothiophene[2,3-d]pyrimidin-3-yl)acetyl hydrazone compounds, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester (one of compound II (II-1))

[0042]

[0043] Cyclohexanone (2.4 grams, 20mmol), ethyl cyanoacetate (3.4 grams, 30mmol), elemental sulfur (0.96 grams, 30mmol), basic alumina (1.8 grams) and morpholine (2.6 grams, 30mmol) were dropped into In a 50mL round bottom flask, place it in a household microwave oven, and react for 15 minutes under 140W microwave radiation. After cooling off, the reaction mixture was separated and purified directly by column chromatography (ethyl acetate / petroleum ether=1 / 10) to obtain 2.0 g of off-white solid (II-1), with a yield of 44%. Mp 112-115°C; 1 H NMR (CDCl 3 , 400MHz) δ1.37(t, 3H), 1.80(m, 4H), 2.53(m, 2H), 2.73(m, 2H), 4.30(q, 2H), 6.00(br, 2H).

Embodiment 2

[0045] 5,6,7,8-tetrahydro-benzo[4,5]thiophene[2,3-d]pyrimidin-4-one (one of compound III (III-1))

[0046]

[0047] 2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester (0.90 g, 4.0 mmol, II-1) was put into formamide (10 mL), stirred at reflux 1.5 hours. After cooling off, the reaction solution was poured into water, suction filtered, washed with water, and dried to obtain 0.74 g of white solid (III-1), with a yield of 90%. Mp 256-259°C; 1 HNMR (400 MHz, DMSO): δ 1.74-1.80 (m, 4H), 2.74 (m, 2H), 2.87 (m, 2H), 8.00 (s, 1H), 12.33 (s, 1H).

Embodiment 3

[0049] Ethyl 4-oxo-5,6,7,8-tetrahydro-benzo[4,5]thiophene[2,3-d]pyrimidine-3-acetate (one of compound IV (IV-1))

[0050]

[0051] 5,6,7,8-Tetrahydro-benzo[4,5]thiophene[2,3-d]pyrimidin-4-one (206 mg, 1 mmol, III-1), ethyl bromoacetate (167 mg , 1 mmol), potassium carbonate (0.2 g, 1.45 mmol) were put into acetone (5 mL), and stirred at 55° C. for 48 hours. The reaction solution was poured into water, extracted with ethyl acetate (20mL×3), the obtained organic layer was dried, filtered, and the solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography (ethyl acetate / petroleum ether=1 / 4 ) separation and purification to obtain 200 mg of white solid (IV-1), yield 68%. Mp 99-102°C; 1 H NMR (DMSO, 400MHz) δ1.23(t, 3H), 1.75-1.82(m, 4H), 2.77(m, 2H), 2.87(m, 2H), 4.19(q, 2H), 4.80(s, 2H), 8.36(s, 1H).

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Abstract

The invention discloses N'-arylmethylene-2-(4-oxothiophene[2,3-d]pyrimidin-3-yl)acetyl hydrazone compounds, and a preparation method and application thereof. The structural general formula of the compounds is shown as a formula (I). Experimental results indicate that the compounds can induce cells to which Caspase-3 in human cervical carcinoma cells, human lung carcinoma cells and human breast carcinoma cells is dependent to die so as to inhibit the propagation of the carcinoma cells, also have low toxicity on normal cells, and can be used for preparing antitumor medicines for treating cervical carcinoma, lung cancer or breast cancer.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, in particular to N'-aryl methylene-2-(4-oxothieno[2,3-d]pyrimidin-3-yl)acetylhydrazone compounds, a preparation method and use. Background technique [0002] Apoptosis is a regulated programmed death process of cells and one of the basic ways of cell death. Apoptosis is a mechanism for multicellular organisms to remove redundant cells or abnormal cells, and plays an important role in the evolution of organisms, the maintenance of internal environment stability, and the development of various systems. The disorder of apoptosis process is directly related to the occurrence of various diseases. Since the end of the 1990s, the relationship between apoptosis and tumorigenesis has gradually attracted the attention of researchers. In the past, people believed that tumors were diseases caused by the excessive proliferation of abnormal cells, so inhibiting the growth of tumo...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/519A61P35/00
Inventor 王任小李剑刘真楼江平张政希周宓郑庶
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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