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Indene-1-subunit sulfonyl benzoyl hydrazine derivative as well as preparation method and application thereof

A technology of sulfenyl benzoyl hydrazide and derivatives is applied in the field of indene-1-sulfenyl benzoyl hydrazide derivatives and their preparation, and can solve the problems of low selectivity, high toxicity and the like

Inactive Publication Date: 2016-10-05
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional chemotherapy drugs mainly act on DNA, RNA and tubulin, which are common components related to the life and death of all cells, resulting in low selectivity and high toxicity

Method used

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  • Indene-1-subunit sulfonyl benzoyl hydrazine derivative as well as preparation method and application thereof
  • Indene-1-subunit sulfonyl benzoyl hydrazine derivative as well as preparation method and application thereof
  • Indene-1-subunit sulfonyl benzoyl hydrazine derivative as well as preparation method and application thereof

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preparation example Construction

[0058] The preparation method of the indene-1-ylidene sulfonyl benzoyl hydrazide derivative shown in above-mentioned formula I, its synthetic steps are:

[0059] 1) at In THF (tetrahydrofuran), m-chlorosulfonylbenzoic acid was added dropwise at 0°C, and then reacted at room temperature for 8-12h to obtain intermediate 2;

[0060] 2) dissolving the carboxylic acid in methanol, adding a catalytic amount of concentrated sulfuric acid dropwise, and reacting with intermediate 2 to obtain intermediate 3;

[0061] 3) Dissolving intermediate 3 in methanol, adding 2 to 5 eq of hydrazine hydrate, and reacting at 65 to 70°C for 12 hours to obtain intermediate 4;

[0062] 4) Intermediate 4 is then combined with reaction to obtain the compound of formula I.

[0063] Wherein, in the preparation method of the above-mentioned indene-1-ylidenesulfonylbenzohydrazide derivatives, the m-chlorosulfonylbenzoic acid described in step 1) and The molar ratio is 1:3.

[0064] Wherein, in the ab...

Embodiment 1

[0069] Example 1 Preparation of 3-(morpholinesulfonyl)benzoic acid (intermediate 2-1)

[0070]

[0071] Dissolve morpholine (300mg) in 5mL tetrahydrofuran, add a solution of m-chlorosulfonylbenzoic acid (250mg) in tetrahydrofuran (3mL) dropwise at 0°C, after the addition, react at room temperature for 12h, and purify by column chromatography to obtain 160mg of a white solid , yield 52%.

[0072] 1 H NMR (400MHz, CDCl 3 ): δ11.46(s, 1H), δ8.15(s, 1H), δ7.96(d, J=7.6Hz, 1H), δ7.84(t, J=7.7Hz, 1H), δ7. 35 (d, J=7.6Hz, 1H), δ3.64 (brs, 4H), δ3.11 (brs, 4H) ppm.

Embodiment 2

[0073] Example 2 Preparation of 3-(N-methylpiperazinesulfonyl)benzoic acid (intermediate 2-2)

[0074]

[0075] Dissolve N-methylpiperazine (340mg) in 5mL tetrahydrofuran, add m-chlorosulfonylbenzoic acid (250mg) in tetrahydrofuran (3mL) dropwise at 0°C, after the addition, react at room temperature for 12h, and purify by column chromatography 166mg of white solid was obtained, the yield was 53%.

[0076] 1 H NMR (400MHz, CDCl 3 ): δ11.46(s, 1H), δ8.15(s, 1H), δ7.96(d, J=7.6Hz, 1H), δ7.84(t, J=7.7Hz, 1H), δ7. 35 (d, J=7.6Hz, 1H), δ3.64 (brs, 4H), δ3.11 (brs, 4H), δ2.26 (s, 3H) ppm.

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Abstract

The invention belongs to the field of chemistry and medicines and particularly relates to an indene-1-subunit sulfonyl benzoyl hydrazine derivative as well as a preparation method and application thereof. The invention provides an indene-1-subunit sulfonyl benzoyl hydrazine derivative, wherein the structure is shown by formula I. The invention also provides a preparation method and application of the indene-1-subunit sulfonyl benzoyl hydrazine derivative shown by the formula I. The indene-1-subunit sulfonyl benzoyl hydrazine derivative provided by the invention has a relatively good inhibitory effect on the proliferation of tumor cells and provides a new option for the field of anti-tumor drug preparation.

Description

technical field [0001] The invention belongs to the field of chemistry and medicine, and specifically relates to indene-1-ylidenesulfonylbenzohydrazide derivatives and their preparation methods and applications. Background technique [0002] Malignant tumors are one of the most serious diseases that threaten human life and health, and have become the second leading cause of death in humans next to cardiovascular diseases. Moreover, the latest statistics show that worldwide, especially in developing countries, the incidence and mortality of malignant tumors have been increasing year by year. Chemotherapy is the most important treatment for malignant tumors besides surgery and radiotherapy. Traditional chemotherapeutic drugs mainly act on common components related to the life and death of all cells, such as DNA, RNA, and tubulin, resulting in low selectivity and high toxicity. Targeted therapy drugs, which act on key molecules and signal transduction pathways that regulate c...

Claims

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Application Information

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IPC IPC(8): C07C311/16C07C311/20C07C311/21C07C303/40C07D295/26C07D265/30A61K31/18A61K31/5375A61K31/496A61K31/54A61K31/551A61P35/00
CPCC07C303/40C07C311/16C07C311/20C07C311/21C07D265/30C07D295/26
Inventor 赵灜兰杨胜勇魏于全
Owner SICHUAN UNIV
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