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Amide compounds with antitumor activity and application of amide compounds

An amide compound, anti-tumor activity technology, applied in the field of medicine, to achieve good inhibitory effect

Inactive Publication Date: 2014-04-30
SHAANXI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the future, finding new anti-tumor drugs with no toxic side effects and high efficiency may become a major development direction. Antimetabolites, topoisomerase inhibitors and tubulin inhibitors will be further developed. Molecular targeted drugs such as angiogenesis inhibitors will be further developed. , protein tyrosine kinase inhibitors, etc. will develop rapidly, and gene therapy drugs will still develop in a tortuous way, but the research and development of new anti-tumor drugs still need a long process to achieve a real cure for tumors

Method used

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  • Amide compounds with antitumor activity and application of amide compounds
  • Amide compounds with antitumor activity and application of amide compounds
  • Amide compounds with antitumor activity and application of amide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Synthesis of Compound (1)

[0045]

[0046] Dissolve 1.6 g of 4-aminophenoxycarbonyl chloride, 7.98 mmol, 1.05 N (N represents the molar ratio) in 8 mL of dichloromethane, and then add 3,4-dichloromethane dropwise at 0°C under nitrogen protection. Methylaniline 970mg, 8.00mmol, 1.05N was dissolved in 12mL of dichloromethane mixed solution, continued stirring for 2h after the dropwise addition, and then added N-ethyl-N isopropylpropyl-2-amine 1.47g, 11.38g mmol, 1.50N and 2-nitro-5-(piperidinyl-1) phenylhydrazine 2.0g, 7.26mmol, 1.00N, 96%, stir for 3h, add dichloromethane 150mL to dilute, use 200mL saturated sodium chloride It was dissolved in water and washed 3 times, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and finally separated and purified by silica gel column chromatography. Yellow solid 4-(3,4-dimethylphenyl)-1-(2-nitro-5-(piperidinyl-1)benzoyl) semi-bisemicarbazide 2.0 g, yield 67%, ( ES,m / z):412.2[M+H] +1 .

[0...

Embodiment 2

[0050] Example 2: Synthesis of Compound (2)

[0051]

[0052] Dissolve benzoyl isothiocyanate 1.5g, 9.09mmol, 1.00N in acetone 15mL, then add 3-(trifluoromethyl)aniline 1.5g, 9.32mmol, 1.02N, the whole system was stirred at 0 °C overnight , concentrated under reduced pressure to obtain off-white solid 1-benzoyl-3-(3-(trifluoromethyl)phenyl)thiourea 2.7g, yield 92%, (ES, m / z): 325.2[M+ H] +1 , 327.2[M+H+2] +1 .

[0053] The above-mentioned off-white solid 3.2g, 9.88mmol, 1.00N was dissolved in 50mL methanol, then sodium hydroxide 565mg, 14.12mmol, 1.43N, purified water 40mL was added, and the whole system was stirred at 80°C for 2h and concentrated under reduced pressure. Extracted with 30 mL×3 of methane, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2 g of 1-(3-(trifluoromethyl)phenyl)thiourea as a light yellow solid, yield 92%, (ES, m / z) :221.2[M+H] +1 , 223.2[M+H+2] +1 .

[0054] The above-mentioned light yellow solid 1g, 4...

Embodiment 3

[0058] Example 3: Synthesis of Compound (3)

[0059] The difference from Example 1 is that 2-nitro-5-(piperidine-1)-thio-benzylmethylhydrazine is used as a raw material, and compound (3) can be obtained according to the synthetic method of Example 1. ), the specific structural formula is as follows:

[0060]

[0061] (ES,m / z):635.2[M+H] +1 , 637.2[M+H+2] +1 ;HNMR(300MHz, CDCl 3 )δ:9.05-9.02(d,J=9.3Hz,1H),8.45(s,1H),8.24-8.13(m,2H),8.10-7.87(m,2H),7.84-7.70(m,1H) ,7.51-7.45(m,3H),7.29-7.26(d,J=7.8Hz,1H),3.98-3.95(s,2H),3.72-3.64(m,4H),3.45-3.41(m,2H) ,3.26-3.19(m,5H),3.12-3.08(m,2H),2.52(s,3H),2.08-2.06(m,4H),1.86-1.85(m,2H),1.37-1.29(m, 6H). See image 3 .

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Abstract

The invention belongs to the technical field of medicines and particularly relates to amide compounds with antitumor activity and an application of the amide compounds. The amide compounds are as shown in the general formula (I), wherein R1 and R2 can be same or different and are respectively and independently selected from hydrogen, halogen, a cyan, hydroxyl, halogenated alkyl, alkoxy, alkoxylalkyl, alkylamino or alkylaminoalkyl; R3 is triazole, 1, 3, 4-oxa-diazole, carbonyl and respective corresponding electro-withdrawing or electron donating substituent groups; and X is carbon or nitrogen atoms. A pharmacological activity result of the amide compounds provided by the invention shows that the amide compounds have favorable inhibiting effect for tumor cell strains.

Description

technical field [0001] The invention belongs to the technical field of medicine, in particular to an amide compound with antitumor activity and its application. Background technique [0002] Tumor has become the second killer that threatens human life. Among the more than 5 billion people in the world, 6.9 million people die from malignant tumors every year on average, and 8.7 million new cases are diagnosed, and the number is increasing year by year. Therefore, governments, research institutions and pharmaceutical companies have long attached great importance to tumor research and anti-tumor drugs, and significant progress has been made in the research of anti-tumor drugs. In recent years, the development of molecular oncology and molecular pharmacology has gradually clarified the nature of tumors; the invention and application of advanced technologies such as large-scale rapid screening, combinatorial chemistry, and genetic engineering have accelerated the process of drug ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D401/12C07D249/14C07D241/20A61K31/4545A61K31/454A61K31/497A61P35/00A61P35/02
CPCC07D241/20C07D249/14C07D401/12C07D413/12
Inventor 卢久富
Owner SHAANXI UNIV OF TECH