Sulfonamide compound and medicinal compositions thereof, and preparation methods and applications thereof

A compound, benzenesulfonamide-based technology, applied in the direction of drug combination, sulfonamide preparation, organic chemistry, etc., can solve problems such as the limitation of tumor therapeutic effect

Active Publication Date: 2013-07-10
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

[0004] However, due to various side effects, such as neurotoxicity and myelosuppression, the therapeutic effect of microtubule-targeted drugs on tumors is limited.

Method used

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  • Sulfonamide compound and medicinal compositions thereof, and preparation methods and applications thereof
  • Sulfonamide compound and medicinal compositions thereof, and preparation methods and applications thereof
  • Sulfonamide compound and medicinal compositions thereof, and preparation methods and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0152] Compound preparation

[0153] The compounds represented by general formula V and general formula X of the present invention can be prepared according to the following scheme and referring to synthetic methods known in the art. In general, in the preparation schemes described below, each reaction is carried out at -10°C to reflux temperature, usually at room temperature (about 25°C) to reflux temperature. Preferably, the reaction temperature is 5-100°C, more preferably 20-80°C. The reaction time is usually not particularly limited, and generally ranges from 1 minute to 24 hours, preferably from 1 to 20 hours. Wherein, the solvent used is usually a polar solvent, such as water, DMF, alcohol (such as methanol, ethanol, isopropanol, etc.). Synthesized compounds can be used physical and chemical methods, such as hydrogen spectrum ( 1 H-NMR), mass spectrometry (MS) and elemental analysis for structural identification.

[0154] A preparation method of a compound of formula...

Embodiment 1

[0194] Compound 4e: N-(4-aminophenyl)-2-(4-methyl-N-(3-(trifluoromethyl)phenyl)benzenesulfonamido)acetamide

[0195]

[0196] Step 1: 4-Methyl-N-(3-(trifluoromethyl)phenyl)benzenesulfonamide

[0197] Dissolve m-trifluoromethylaniline (1.61g, 10mmol), TsCl (1.91g, 10mmol), DMAP (1.34g, 11mmol) in dichloromethane (30ml), stir at room temperature for 30 minutes, then wash with saturated NaHCO 3 Wash (10ml*3), saturated NaCl wash (10ml*3), anhydrous NaCl 2 SO 4 Drying and column chromatography gave product a as a white solid (2.9 g, 92%). Mp = 80-82°C, 1 HNMR (CDCl 3 , 300MHz) δ: 2.39(s, 3H), 6.97(s, 1H), 7.24-7.37(m, 6H), 7.68(d, J=8.1Hz, 2H).

[0198] Step 2: tert-butyl 2-(4-methyl-N-(3-(trifluoromethyl)phenyl)benzenesulfonamido)acetate

[0199] Compound a (540mg, 1.7mmol) was dissolved in DMF (10ml), potassium carbonate (480mg, 3.4mmol) and tert-butyl bromoacetate (380μl, 2.6mmol) were added successively, stirred at room temperature for 2h, and then diluted with 50ml of ...

Embodiment 2

[0205] Compound 1a: 4-Methyl-N-(3-(trifluoromethyl)phenyl)benzenesulfonamide

[0206]

[0207] It was synthesized by the method shown in step 1 in Example 1.

[0208] white solid. 1 H NMR (300MHz, CDCl 3 )δ7.74(d, 2H), 7.38-7.21(m, 4H), 6.91(d, 2H), 3.83(s, 3H).

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Abstract

The invention discloses a sulfonamide compound and medicinal compositions thereof, and preparation methods and applications thereof. The sulfonamide compound can be used as a micro-molecular tubulin inhibitor, has an anti-microtubule effect in vitro, can induce the apoptosis of tumor cells in vitro, has an obvious inhibition effect on multidrug resistance cells in vitro, and has a substantial in-vivo oral antitumor activity. Additionally, the compound has the advantages of small molecular weight, simple synthesis, and small toxic side effects. The invention also provides medicinal compositions containing the sulfonamide compound and pharmaceutically acceptable salts thereof as an active component.

Description

technical field [0001] The invention belongs to the field of medicines, and in particular relates to a new sulfonamide compound, a pharmaceutical composition, a preparation method and an application thereof. Background technique [0002] Tumor is a kind of disease characterized by uncontrolled cell growth and proliferation. Abnormalities in cell proliferation, differentiation and apoptosis are all involved in the occurrence and development of tumors. Chemotherapy is one of the main treatment methods for malignant tumors. According to the different sensitivity of chemotherapy drugs to tumor cells at different stages, chemotherapy drugs can be divided into two categories: the first category is cell cycle non-specific drugs (CCNSA): these drugs It can kill tumor cells in all phases of the cell cycle, including G0 phase (quiescent cell population) cells. Such drugs include alkylating agents, anticancer antibiotics, and hormones. The second category is cell cycle-specific drugs...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/21C07C311/08C07D249/14C07D213/75C07D209/08C07C311/29C07D239/88C07C311/48C07C303/40C07C303/38A61K31/216A61K31/198A61K31/18A61K31/4196A61K31/4406A61K31/404A61K31/517A61P35/00A61P35/02
Inventor 俞强龙亚秋刘祖龙薛丁周足宇
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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