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1-aryl-3-substituted-5-substituted amino-4-pyrazolecarboxamide compounds and their applications

A pyrazole carboxamide and compound technology, applied in the field of medicine, can solve the problems of poor selectivity, toxic and side effects, etc.

Inactive Publication Date: 2014-10-29
SHAANXI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing anti-tumor drugs have problems such as poor selectivity, toxic side effects, and drug resistance.

Method used

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  • 1-aryl-3-substituted-5-substituted amino-4-pyrazolecarboxamide compounds and their applications
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  • 1-aryl-3-substituted-5-substituted amino-4-pyrazolecarboxamide compounds and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of compound (1)

[0033]

[0034] Adopt the mode of synthetic route I:

[0035] 2-Cyanoacetamide (3.36 g, 39.96 mmol) was dissolved in a 250 mL round bottom flask with 7 mL of acetic acid, and 1,1,1-triethoxyethane (7.13 g, 43.95 mmol) was added to the flask , the whole reaction system was stirred overnight at 100° C., and after the reaction was completed, it was lowered to room temperature. Add 15 mL of diethyl ether to the reaction system, and at the same time collect the resulting solid by filtration and dry to obtain 3.3 g of white solid 2-cyano-3-ethoxybutyl-2-enamine, melting point: 95-97°C, yield 54 %, (ES, m / z): 155.2 [M+H] +1 .

[0036] 2-Cyano-3-ethoxybutyl-2-enamine (1.0 g, 6.49 mmol) was dissolved in 15 mL of methanol in a 50 mL round bottom flask while phenylhydrazine (840 mg, 7.77 mmol) was added. The whole reaction system was stirred overnight at 80° C., and the reaction was completed. The reaction solution was concentr...

Embodiment 2

[0038] Embodiment 2: Using 1-pyridine-4-piperidine-4-formyl chloride as a reagent, according to the synthetic route I, compound (2) can be prepared

[0039]

[0040] Mp (melting point): 101~103℃; (ES, m / z): 421.2[M+H] +1 ; 1 H NMR (300MHz, DMSO) δ: 1.30(s, 2H), 1.64~1.68(m, 2H), 1.93~1.97(m, 2H), 2.46(s, 3H), 2.89(brs, 1H), 4.02( s, 3H), 4.15 (d, 2H), 7.10-7.12 (m, 2H), 7.45-7.52 (m, 5H), 8.10-8.13 (m, 2H). See figure 2 .

Embodiment 3

[0041] Embodiment 3: Using 1-(azetidine-3)-piperidine-4-formyl chloride as a reagent, according to the synthetic route I, the synthesis of compound (3) can be obtained

[0042]

[0043] Mp (melting point): 121~123℃; (ES, m / z): 383.2[M+H] +1 ; 1 H NMR (300MHz, DMSO) δ: 1.88~2.05(4H, m), 2.48(3H, s), 2.63~2.69(1H, m), 2.80(2H, t), 3.20~3.30(2H, m), 4.06-4.12 (1H, m), 4.26-4.45 (4H, m), 7.42-7.56 (5H, m). See image 3 .

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Abstract

The invention discloses a 1-aryl-3-substituent-5-substituted amino-4-pyrazole formamide compound and application thereof. The 1-aryl-3-substituent-5-substituted amino-4-pyrazole formamide compound has a general structural formula described in the specification, wherein R1 and R2 can be hydrogen, benzyl or alkyl independently, or can form the following groups comprising imidazolidinyl, 2-imidazolidinyl, 3-imidazolidinyl, pyrryl, 2H-pyrryl, 2-pyrrolinyl, pyrrolidyl, triazolyl, pyrazolyl, piperazinyl, pyridazinyl, pyrazinyl, triazinyl, morpholinyl and thio-morpholinyl, together with N connected with R1 and R2; R1 and R2 can be the same or different; R3 can be any one of H, CF3, Br, NO2, CH3 and OCH3; and R4 can be hydrogen, halogen, cyan, hydroxy, alkyl halide, alkoxy, alkoxy alkyl, alkyl sulphanyl or alkyl sulphanyl alkyl. The pharmacological activity result of the compound shows that the compound has an excellent restraining effect on tumor cell lines.

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a novel 1-aryl-3-substituted-5-substituted amino-4-pyrazolecarboxamide compound and its application. Background technique [0002] Tumor is a major chronic disease that plagues the health of modern people. It has high morbidity, high mortality, high recurrence rate, and difficult treatment. About 7 million people die of cancer in the world every year, accounting for about a quarter of the total number of deaths. Among them, breast cancer and ovarian cancer are the main malignant tumors that endanger women's health. About 1.2 million women in the world develop breast cancer every year. At present, the mortality rate of existing cancer patients in our country exceeds 30%, which has become the second largest factor in the death of Chinese residents. Drug therapy has become an effective and widely used treatment method for malignant tumors. In 2010, the global sales of antineopla...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/38C07D401/14C07D401/04C07D403/14A61K31/415A61K31/4155A61K31/4178A61K31/4192A61K31/4196A61K31/4545A61K31/496A61K31/497A61K31/506A61K31/53A61K31/535A61K31/541A61P35/00
Inventor 卢久富
Owner SHAANXI UNIV OF TECH