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Synthesis for sulfaphenazole acylhydrazone derivatives and application of sulfaphenazole acylhydrazone derivatives in anti-cancer drugs

A technology of sulfaphenylpyrazole acylhydrazone and sulfaphenizone acylhydrazone, which is applied in the synthesis of a class of sulfaphenizone pyrazole acylhydrazone derivatives and the application field in anticancer drugs, and can solve the limitation of application range and the use of Reduced range, no bactericidal effect, etc.

Inactive Publication Date: 2015-11-11
NANJING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Sulfonamides have a variety of biological activities and have always been a research hotspot in the field of medicinal chemistry. They are widely used in antibacterial, hypotensive, diuretic, etc. However, these drugs are bacteriostatic agents without bactericidal effect, and are prone to drug resistance Sexuality and frequent use will produce many adverse reactions, so its application range is greatly limited
However, due to its tendency to produce drug resistance, the scope of use has been gradually reduced

Method used

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  • Synthesis for sulfaphenazole acylhydrazone derivatives and application of sulfaphenazole acylhydrazone derivatives in anti-cancer drugs
  • Synthesis for sulfaphenazole acylhydrazone derivatives and application of sulfaphenazole acylhydrazone derivatives in anti-cancer drugs
  • Synthesis for sulfaphenazole acylhydrazone derivatives and application of sulfaphenazole acylhydrazone derivatives in anti-cancer drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: Preparation of 4-(3-(benzoylhydrazone)-5-(4-methoxyphenyl)-1H-pyrazole)benzenesulfonamide

[0016]

[0017] Under stirring, 5-(4-methoxyphenyl)pyrazole hydrazide benzenesulfonamide (0.1g, 0.25mmol), ethanol (10mL), benzaldehyde (0.039g, 0.375mmol), acetic acid (0.5mL) Add to a 50mL round-bottom flask, react at room temperature for 12h, TLC follows the reaction (developer V AcOEt : V PE =1:2), after the reaction, filter, wash the solid with cold ethanol and distilled water in turn, and finally vacuum dry. The obtained solid is dissolved in absolute ethanol and recrystallized and purified to obtain the powdery target compound.

[0018] A white solid was obtained with a yield of 60%.m.p.251~253℃; 1 HNMR(DMSO-d 6 , 300MHz) δ: 11.81 (s, 1H, CONH), 8.55 (s, 1H, CHN), 7.90 (d, J = 6.3 Hz, 2H, ArH), 7.72 (d, J = 5.1 Hz, 2H, ArH) , 7.60(d, J=6.3Hz, 2H, ArH), 7.48(t, J=6.3Hz, 5H, ArHandSO 2 NH 2 ), 7.27(d, J=6.5Hz, 2H, ArH), 7.12(s, 1H, CH), 6.98(d, J=6.4Hz, 2H, ArH), 3.7...

Embodiment 2

[0019] Example 2: Preparation of 4-(3-(4-methoxybenzoylhydrazone)-5-(4-methoxyphenyl)-1H-pyrazole)benzenesulfonamide

[0020]

[0021] The preparation method is the same as in Example 1. White solid, yield 41%, m.p.169~171℃; 1 HNMR(DMSO-d 6 , 300MHz) δ: 11.66 (s, 1H, CONH), 8.48 (s, 1H, CHN), 7.89 (t, J=6.4Hz, 2H, ArH), 7.66 (d, J=6.5Hz, 2H, ArH) , 7.59(d, J=6.4Hz, 2H, ArH), 7.49(s, 2H, SO 2 NH 2 ), 7.26 (d, J = 6.5 Hz, 2H, ArH), 7.10 (s, 1H, CH), 7.03 (d, J = 6.5 Hz, 2H, ArH), 6.98 (d, J = 6.5 Hz, 2H, ArH), 3.82(s, 3H, OCH 3 ), 3.78(s, 3H, OCH 3 ).ESI-MS: 506.1[M+H] + .Anal.CalcdforC 25 H 23 N 5 O 5 S: C, H, N.

Embodiment 3

[0022] Example 3: Preparation of 4-(3-(2-methoxybenzoylhydrazone)-5-(4-methoxyphenyl)-1H-pyrazole)benzenesulfonamide

[0023]

[0024] The preparation method is the same as in Example 1. A white solid was obtained with a yield of 58.6%. m.p. 157~160℃; 1 HNMR(DMSO-d 6 , 300MHz) δ: 11.86 (s, 1H, CONH), 8.89 (s, 1H, CHN), 7.89 (t, J=6.4Hz, 3H, ArH), 7.60 (d, J=6.4Hz, 2H, ArH) , 7.50(s, 2H, SO 2 NH 2 ), 7.43 (t, J = 6.4 Hz, 1H, ArH), 7.27 (d, J = 6.5 Hz, 2H, ArH), 7.12 (d, 2H, CHandArH), 7.04 (t, J = 5.6 Hz, 1H, ArH), 6.99(d, J=6.5Hz, 2H, ArH), 3.87(s, 3H, OCH 3 ), 3.79(s, 3H, OCH 3 ).ESI-MS: 506.1[M+H] + .Anal.CalcdforC 25 H 23 N 5 O 5 S: C, H, N.

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Abstract

The invention discloses synthesis for sulfaphenazole acylhydrazone derivatives which are characterized by having the following general formula: FORMULA as shown in the specification. The sulfaphenazole acylhydrazone derivatives have obvious inhibiting effect on lung cancer cells (A549), especially have certain inhibiting effect on liver cancer cells (HepG2) by virtue of part of compounds 46 and 48, and show cell toxicity, which is equivalent to or superior to that of a positive control drug, on human kidney epithelial cells (293T). And therefore, the sulfaphenazole acylhydrazone derivatives disclosed by the invention can be applied in preparing anti-tumor drugs. The invention further discloses a preparation method and anti-tumor biological activity of the sulfaphenazole acylhydrazone derivatives.

Description

Summary of the invention [0001] The purpose of the present invention is to provide the synthesis of a class of sulfaphenazole hydrazone derivatives and their application in anticancer drugs Background technique [0002] Sulfonamides have a variety of biological activities and have always been a hot research topic in the field of medicinal chemistry. They are widely used in antibacterial, blood pressure, and diuretic applications. However, these drugs are antibacterial agents and have no bactericidal effect and are prone to drug resistance. Sex and regular use will produce many adverse reactions, which greatly limits the scope of its application. However, due to its susceptibility to 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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IPC IPC(8): C07D231/14A61K31/415A61P35/00
CPCC07D231/14
Inventor 朱海亮卢小院王忠长晏天龙
Owner NANJING UNIV
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