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2-methyl-9-acridine(p-methoxy benzamido)thiourea, preparation method and uses thereof

A technology of acridinium thiourea and methyl, which is applied in the field of 2-methyl-9-acridine thiourea and its preparation, can solve the problem that there are no literature reports on derivatives with dual anti-tumor activities, and achieve anti-cancer effects Good, strong anti-tumor activity, simple preparation method

Active Publication Date: 2015-02-04
嘉兴芸诗娇电子商务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, the derivatives with dual anti-tumor activity combined with the above two have not been reported in the literature.

Method used

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  • 2-methyl-9-acridine(p-methoxy benzamido)thiourea, preparation method and uses thereof
  • 2-methyl-9-acridine(p-methoxy benzamido)thiourea, preparation method and uses thereof
  • 2-methyl-9-acridine(p-methoxy benzamido)thiourea, preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1 Preparation of 2-methyl-9-acridine (p-methoxybenzamido) thiourea

[0017] 1) In a 250mL three-necked flask, add 5.20g (26mmoL) of o-bromobenzoic acid, 3.64g (34mmoL) of p-methylaniline, 7.5g (36.2mmoL) of potassium carbonate and 0.3g (4.7mmoL) of copper powder, and then add 30 mL of isoamyl alcohol was used as a solvent, and stirred under reflux at 140° C. for 2 h. After the reaction, evaporate the solvent under reduced pressure, add 600 mL of water to the obtained residue, react at 80°C for 20 minutes, filter while hot, wash the filter cake, combine the water layer, acidify the water layer with concentrated hydrochloric acid to pH=2, and precipitate a large amount of light yellow Precipitate, filter with suction, and recrystallize the obtained solid with chloroform to obtain compound N-(p-methylphenyl)anthranilic acid (Formula II), with a yield of 77%;

[0018] 2) In a 100 mL round bottom flask, add the compound represented by formula II (18 moL) and 14.37 m...

Embodiment 2

[0021] Embodiment 2 Identification and analysis of compounds of the present invention

[0022] 2-methyl-9-acridine (p-methoxybenzamido) thiourea obtained by the above method 1 After H NMR nuclear magnetic resonance spectrum, FT-IR infrared spectrum, melting point and other tests, its chemical structure was confirmed by analysis.

[0023] The physical and chemical properties are as follows:

[0024] 1) Appearance: orange-yellow powder

[0025] 2) Melting point: 200~206℃

[0026] 3) Molecular weight: 416.50

[0027] 4) Molecular formula: C 23 h 20 N 4 o 2 S, the structural formula is as follows:

[0028]

[0029] 5) 1 H NMR nuclear magnetic resonance spectrum: the sample was dissolved in deuterated dimethyl sulfoxide (DMSO-d 6 ), measured at 400MHz, the obtained spectrum data are: δ: 11.26 (br, s, 1H, -NH), 10.41 (br, s, 1H, -NH), 10.22 (br, s, 1H, -NH), NH), 8.80(s, 2H, ArH), 8.05~8.15(m, 3H, ArH), 7.93(s, 2H, ArH), 7.77(t, 1H, ArH), 7.63(t, 1H, ArH), 8.15(d, 1H,...

Embodiment 3

[0031] Example 3 In Vitro Antitumor Activity Experiment

[0032] In vitro cytotoxicity assays were performed using the MTT method. The following four cell lines were used in the experiment: gastric cancer cell MGC-803, liver cancer cell BEL-7404, large cell lung cancer cell NCI-H460 and bladder cancer cell T24. 5-FU and cisplatin were used as reference substances. Data analysis Origin software was used for data processing.

[0033] experimental method:

[0034] 1) The selected cell lines were placed at 37°C, 5% CO 2 In an incubator under fully humidified conditions, inoculate and culture in PPMI1640 medium containing 10% inactivated newborn calf serum. Use an inverted microscope to observe the growth of the cells, replace the medium 2-3 times a week, passage once every 6-7 days, digest and passage with 0.25% trypsin when inoculating, usually take 3-4 passages, and use it for cells in the logarithmic growth phase in the experiment.

[0035] 2) Accurately weigh the sample ...

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Abstract

The invention belongs to the technical field of medicine, and relates to an acridine derivative, particularly to 2-methyl-9-acridine(p-methoxyphenyl cresol amine)thiourea, a preparation method and uses thereof, wherein the structure formula is represented as the follow. According to the acridine derivative, the acridine mother nucleus is connected with the active group phenol amine thiourea so as to provide the strong potential biological activity. The results of in vitro anti-tumor tests show that the acridine derivative provides the strong inhibition effects on a variety of tumor cells, and can be used as the anti-tumor drug or the lead compound so as to be further development.

Description

technical field [0001] The invention relates to the technical field of antineoplastic drugs, in particular to 2-methyl-9-acridine (p-methoxybenzamido)thiourea and its preparation method and application. Background technique [0002] Cancer is a malignant disease that seriously threatens public health. Most tumors have poor prognosis, short survival time, lack of curable means, and high unmet clinical needs. In recent years, they have gradually become the leading cause of death. Because of the refractory nature of the disease and the urgency of clinical needs, anti-tumor drugs have always been a hot spot in the research and development of innovative drugs, and in recent years it has become a "hot spot" among the hot spots. According to reports, acridine and its derivatives have a good inhibitory effect on cancer cells, and can be used as anticancer lead compounds in new drug research. And thiosemicarbazide compounds also have many important biological activities, such as an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D219/10A61P35/00
CPCC07D219/10
Inventor 霍丽妮陈睿李培源苏炜
Owner 嘉兴芸诗娇电子商务有限公司
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