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Synthesis method of dihydro-pyrazole sulfonamide derivatives of salicylaldehydes and application of dihydro-pyrazole sulfonamide derivatives to preparation of anticancer drugs

A technology of dihydropyrazole sulfonamide and salicylaldehyde, which is applied in the fields of drug combination, antineoplastic drugs, organic chemistry, etc., and can solve the problems of easy drug resistance, limited application range, adverse reactions, etc.

Inactive Publication Date: 2014-03-26
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since this type of drug is a bacteriostatic agent without a bactericidal effect, it is prone to drug resistance and many adverse reactions will occur when it is used frequently, so its application range is greatly limited.
Especially because of its susceptibility to drug resistance, the scope of use has been gradually reduced

Method used

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  • Synthesis method of dihydro-pyrazole sulfonamide derivatives of salicylaldehydes and application of dihydro-pyrazole sulfonamide derivatives to preparation of anticancer drugs
  • Synthesis method of dihydro-pyrazole sulfonamide derivatives of salicylaldehydes and application of dihydro-pyrazole sulfonamide derivatives to preparation of anticancer drugs
  • Synthesis method of dihydro-pyrazole sulfonamide derivatives of salicylaldehydes and application of dihydro-pyrazole sulfonamide derivatives to preparation of anticancer drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1: Preparation of 4-(5-(2-hydroxyphenyl)-3-phenyl-4,5-dihydropyrazole)benzenesulfonamide (Compound 27)

[0014]

[0015] Under stirring, chalcone (1.0g, 4.46mmol), ethanol (25mL), p-hydrazinobenzenesulfonamide (0.97g, 5.03mmol), and acetic acid (1.0mL) were added to a 50mL round bottom flask. Some solids are insoluble; transfer the flask to an oil bath, reflux the reaction for 6 hours, and follow the reaction by TLC (developer V AcOEt : V Masami alkyl =1:2). After the reaction is completed, filter, wash the solid with distilled water, and finally vacuum dry. The obtained solid is dissolved in absolute ethanol and recrystallized and purified to obtain the crystalline target compound.

[0016] Yellow crystals, the yield is 41.15%.m.p.266~268℃; 1 H NMR (DMSO-d6, 400MHz) δ: 9.95 (s, 1H, OH), 7.79~6.68 (m, 15H, ArH and NH) 2 ), 5.72(dd,J 1 =5.1, J 2 =5.1Hz, 1H, 5-H), 3.95(dd, J 1 =12.2, J 2 =12.1Hz, 1H, 4-H b ), 3.13(dd,J 1 =5.2, J 2 =5.1Hz, 1H, 4-H a ).

Embodiment 2

[0017] Example 2: Preparation of 4-(3-(2-chlorophenyl)-5-(2-hydroxyphenyl)-4,5-dihydropyrazole)benzenesulfonamide (Compound 28)

[0018]

[0019] The preparation method is the same as in Example 1.

[0020] Yellow crystals, the yield is 63.5%.m.p.220~222℃; 1 H NMR (DMSO-d6, 400MHz) δ: 9.93 (s, 1H, OH), 7.80~6.71 (m, 14H, ArH and NH2), 5.73 (dd, J 1 =5.1, J 2 =5.1Hz, 1H, 5-H), 4.09 (dd, J 1 =12.2, J 2 =12.1Hz, 1H, 4-H b ), 3.22(dd,J 1 =5.2, J 2 =5.1Hz, 1H, 4-H a ).

Embodiment 3

[0021] Example 3: Preparation of 4-(3-(4-ethoxyphenyl)-5-(2-hydroxyphenyl)-4,5-dihydropyrazole)benzenesulfonamide (Compound 29)

[0022]

[0023] The preparation method is the same as in Example 1.

[0024] White crystals, the yield is 39.5%.m.p.243~245℃; 1 H NMR (DMSO-d6, 400MHz) δ: 9.94 (s, 1H, OH), 7.72~6.68 (m, 14H, ArH and NH) 2 ), 5.67(dd, J 1 =4.9, J 2 =6.1Hz, 1H, 5-H), 4.06 (m, 2H, OCH 2 ), 3.92(dd,J 1 =12.1, J 2 =12.0Hz, 1H, 4-H b ), 3.08(dd, J 1 =6.9, J 2 =5.0Hz, 1H, 4-H a ), 1.34(t, J=6.9Hz, 3H, CH 3 ).

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Abstract

The invention discloses a synthesis and preparation method of dihydro-pyrazole sulfonamide derivatives of salicylaldehydes. The dihydro-pyrazole sulfonamide derivatives of salicylaldehydes have a remarkable inhibiting effect on human breast cancer cells (MCF-7) and lung cancer cells (A549), so that the dihydro-pyrazole sulfonamide derivatives can be applied to the preparation of anticancer drugs. The invention discloses a synthesis method and anticancer biological activity of the dihydro-pyrazole sulfonamide derivatives.

Description

Technical field [0001] The purpose of the present invention is to provide the synthesis of a class of salicylaldehyde dihydropyrazole sulfonamide derivatives and its application in anticancer drugs Background technique [0002] Sulfonamides have a variety of biological activities and have always been a hot spot in the field of medicinal chemistry. They have been widely used in antibacterial, blood pressure, and diuretic applications. However, because these drugs are bacteriostatic agents and have no bactericidal effect, they are prone to drug resistance and often cause many adverse reactions, which greatly limits their application scope. Especially because of its easy development of drug resistance, its use range has gradually decreased. However, in recent years, the literature has repeatedly reported that its derivatives have other activities in addition to antibacterial activities, the most significant of which is anti-tumor activity. [0003] Pyrazole is an important class of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/06A61P35/00
CPCC07D231/06
Inventor 朱海亮邱寒月王鹏飞严晓强王忠长段勇涛
Owner NANJING UNIV