Preparing method for 4-(3-(3-(4-clocoumarol)-acylhydrazone)-5-phenyl-pyrazol) benzene sulfonamide derivate and application to anti-cancer drugs

A kind of technology of chlorocoumarin and benzenesulfonamide, applied in 4-(3-(3-(4-chlorocoumarin)-acylhydrazone)-5-phenyl-pyrazole)benzenesulfonamide derivatives The preparation and application of anticancer drugs can solve the problems of adverse reactions, reduced scope of use, and easy generation of drug resistance.

Inactive Publication Date: 2015-09-30
NANJING UNIV
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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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  • Preparing method for 4-(3-(3-(4-clocoumarol)-acylhydrazone)-5-phenyl-pyrazol) benzene sulfonamide derivate and application to anti-cancer drugs
  • Preparing method for 4-(3-(3-(4-clocoumarol)-acylhydrazone)-5-phenyl-pyrazol) benzene sulfonamide derivate and application to anti-cancer drugs
  • Preparing method for 4-(3-(3-(4-clocoumarol)-acylhydrazone)-5-phenyl-pyrazol) benzene sulfonamide derivate and application to anti-cancer drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Preparation of 4-(3-(3-(4-chlorocoumarin)-acylhydrazone)-5-phenyl-pyrazole)benzenesulfonamide

[0017]

[0018] Under stirring, 5-phenylpyrazole hydrazide benzenesulfonamide (0.27g, 0.5mmol), ethanol (15mL), 4-chloro-1-benzopyran-2-one (0.12g, 0.6mmol), Acetic acid (0.5mL) was added in a 50mL round-bottomed flask; the reaction was stirred at room temperature for 12h, followed by TLC (developer V AcOEt :V 正己烷 = 1:2), after the reaction, the reaction mixture was added to ice water, filtered, the solid was washed with distilled water, and finally vacuum-dried, and the obtained solid was dissolved in absolute ethanol for recrystallization and purification to obtain the powdery target compound.

[0019] Yellow solid, yield 80.4%, m.p.243~248℃; 1 H NMR (DMSO-d 6 , 300MHz) δ: 12.25 (s, 1H, CONH), 8.74 (s, 1H, CHN), 8.04 (d, J=6.0Hz, 1H, ArH), 7.90 (d, J=6.4Hz, 2H, ArH) , 7.79~7.75(m, 1H, ArH), 7.61(d, J=6.4Hz, 2H, ArH), 7.53(t, J=7.5Hz, 4H, ArH and SO 2 NH ...

Embodiment 2

[0020] Example 2: Preparation of 4-(3-(3-(4-chlorocoumarin)-acylhydrazone)-5-(4-methylphenyl)-pyrazole)benzenesulfonamide

[0021]

[0022] The preparation method is the same as in Example 1. A brown solid was obtained with a yield of 66.8%. m.p.238~241°C; 1 H NMR (DMSO-d 6 , 300MHz) δ: 12.23 (s, 1H, CONH), 8.73 (s, 1H, CHN), 8.03 (d, J=6.0Hz, 1H, ArH), 7.89 (d, J=6.4Hz, 2H, ArH) , 7.78~7.74(m, 1H, ArH), 7.60(d, J=6.4Hz, 2H, ArH), 7.52(d, J=6.0Hz, 4H, ArH and SO 2 NH 2 ), 7.23(s, 4H, ArH), 7.17(s, 1H, CH), 2.32(s, 3H, CH 3 ).ESI-MS: 563.1[M+H] + .Anal.Calcd for C 27 h 20 ClN 5 o 5 S: C, H, N.

Embodiment 3

[0023] Example 3: Preparation of 4-(3-(3-(4-chlorocoumarin)-acylhydrazone)-5-(3-methylphenyl)-pyrazole)benzenesulfonamide

[0024]

[0025] The preparation method is the same as in Example 1. A yellow solid was obtained with a yield of 76.6%. m.p.214~217°C; 1 H NMR (DMSO-d 6 , 300MHz) δ: 12.23 (s, 1H, CONH), 8.74 (s, 1H, CHN), 8.04 (d, J=6.0Hz, 1H, ArH), 7.90 (d, J=6.4Hz, 2H, ArH) , 7.77(t, J=6.0Hz, 1H, ArH), 7.61(d, J=6.4 Hz, 2H, ArH), 7.51(d, J=6.0Hz, 4H, ArH and SO 2 NH 2 ), 7.25(t, J=6.0Hz, 3H, ArH), 7.20(s, 1H, CH), 7.03(d, J=6.0Hz, 1H, ArH), 2.30(s, 3H, CH 3 ).ESI-MS: 563.1[M+H] + .Anal.Calcd for C 27 h 20 ClN 5 o 5 S: C, H, N.

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Abstract

The invention provides synthesis for a 4-(3-(3-(4-clocoumarol)-acylhydrazone)-5-phenyl-pyrazol) benzene sulfonamide derivate. The synthesis is characterized by being implemented according to the general formula (please see the formula in specification). The 4-(3-(3-(4-clocoumarol)-acylhydrazone)-5-phenyl-pyrazol) benzene sulfonamide derivate has the obvious inhibiting effect on culture of cervical cancer cells (Hela), human melanoma cells (F10) and hepatoma carcinoma cells (HepG2) and has cytotoxicity equivalent to or better than that of positive control drugs for human kidney epithelial cells (293T). Accordingly, the 4-(3-(3-(4-clocoumarol)-acylhydrazone)-5-phenyl-pyrazol) benzene sulfonamide derivate can be used for preparing anti-tumor drugs. The invention discloses a preparing method of the benzene sulfonamide derivate and anti-tumor biological activity.

Description

Contents of the invention [0001] The object of the present invention is to provide the preparation method of 4-(3-(3-(4-chlorocoumarin)-acylhydrazone)-5-phenyl-pyrazole) benzenesulfonamide derivatives and their use in anticancer drugs Applications Background technique [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 that its application range is greatly limited. However, due to its easy drug resistance, the scope of use has been gradually reduced. However, the literature in recent years has repeatedly reported that its derivatives have activities other than antibacterial, the most notable of which is antitumor activity. [0003] Pyrazoles are an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12A61K31/4155A61P35/00
CPCC07D405/12
Inventor 朱海亮卢小院王忠长严晓强
Owner NANJING UNIV
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