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2,3-dihydro-1h-quinolin-4-one thiosemicarbazone derivatives and its preparation method and application

A technology of thiosemicarbazone and derivatives, which is applied in the field of medicine and achieves the effects of mild conditions, high efficiency and inhibition of tumor cell proliferation

Active Publication Date: 2020-04-24
LINGNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the research of 2,3-dihydro-1H-quinolin-4-ketone thiosemicarbazones has very great potential in anti-tumor, but there is no relevant 2,3-dihydro-4-ketone in the prior art. Report on 1H-quinolin-4-one thiosemicarbazone derivatives as active ingredients of antineoplastic drugs

Method used

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  • 2,3-dihydro-1h-quinolin-4-one thiosemicarbazone derivatives and its preparation method and application
  • 2,3-dihydro-1h-quinolin-4-one thiosemicarbazone derivatives and its preparation method and application
  • 2,3-dihydro-1h-quinolin-4-one thiosemicarbazone derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Example 1 Synthesis of 8-fluoro-2,3-dihydro-1H-quinolin-4-one thiosemicarbazone

[0077] (1) Synthesis of 3-(o-fluoroanilino)propionic acid

[0078] Add 13.74mmol of 2-fluoroaniline, 16.48mmol of methyl acrylate, and 3.435mmol of glacial acetic acid to a 250mL round-bottomed flask, and heat to reflux at 80°C for 8h; then add 58mmol of sodium hydroxide, 25mL of water, and 25mL of methanol in sequence, Under the condition of 94°C, the hydrolysis reaction occurred in the round bottom flask for 20 hours; the reaction was tracked and monitored by TLC, after the reaction was completed, cooled to room temperature (20-25°C), adjusted the pH value to 4-5 with concentrated hydrochloric acid, and then used 25mL acetic acid Ethyl is extracted until the organic layer is colorless; then, the rotary evaporator removes the solvent to obtain a white solid product, which is 3-(o-fluoroanilino)propionic acid, and its productive rate is 64%. Its structural formula is:

[0079] NMR 1 H-...

Embodiment 2

[0088] Example 2 Synthesis of 6,7-difluoro-2,3-dihydro-1H-quinolin-4-one thiosemicarbazone

[0089] (1) Synthesis of 3-(3,4-difluoroanilino)propionic acid

[0090] According to the preparation method of step (1) in Example 1, other conditions remain unchanged, and an equivalent amount of 3,4-difluoroaniline is used instead of 2-fluoroaniline to obtain a brown oily liquid product, which is 3-(3,4- Difluoroanilino) propionic acid, its productive rate is 40%, and its structural formula is:

[0091] NMR 1 H-NMR (CDCl 3 ,400MHz): δ6.95(1H,ArH,m), 6.43(2H,ArH,m), 6.29(1H,ArH,d), 3.41(2H,CH 2 ,t), 2.65(2H,CH 2 ,t).

[0092] (2) Synthesis of 6,7-difluoro-2,3-dihydro-1H-quinolin-4-one

[0093]According to the preparation method of step (2) in Example 1, with other conditions unchanged, an equivalent amount of 3-(3,4-difluorophenylamino)propionic acid was used instead of 3-(o-fluorophenylamino)propionic acid to obtain the product It is a yellow powder product, namely 6,7-difluo...

Embodiment 3

[0100] Example 3 Synthesis of 5,6,7-trifluoro-2,3-dihydro-1H-quinolin-4-one thiosemicarbazone

[0101] (1) Synthesis of 3-(3,4,5-trifluoroanilino)propionic acid

[0102] According to the preparation method of step (1) in Example 1, other conditions remain unchanged, and an equivalent amount of 3,4,5-trifluoroaniline is used instead of 2-fluoroaniline to obtain a reddish-brown oily product, which is 3-(3, 4,5-trifluoroanilino) propionic acid, its productive rate is 72.7%, and its structural formula is:

[0103] NMR 1 H-NMR (CDCl 3 ,400MHz): δ6.19(2H,ArH,dd), 3.39(2H,CH 2 , dd), 2.66 (2H, CH 2 ,t).

[0104] (2) Synthesis of 5,6,7-trifluoro-2,3-dihydro-1H-quinolin-4-one

[0105] According to the preparation method of step (2) in Example 1, other conditions remain unchanged, replace 3-(o-fluoroanilino) propionic acid with an equivalent amount of 3-(3,4,5-trifluoroanilino) propanoic acid, A brown powder product was obtained, which was 5,6,7-trifluoro-2,3-dihydro-quinolin-4...

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Abstract

The invention discloses 2,3-dihydro-1H-quinoline-4-ketone thiosemicarbazone derivatives as well as a preparation method and application thereof. The structural formula of the derivatives is as shown in a formula (I): (the formula is as shown in the description), wherein R1 is halogen, alkyl or alkoxy; R2 is hydrogen, halogen or alkoxy; R3 is hydrogen or halogen; R4 is hydrogen or halogen; X is hydrogen, acetyl or nitryl; and Y is hydrogen or phenyl. The derivatives can obviously inhibit proliferation of tumor cells, and has significant inhibition effect on multiple cancer cell strains such asbreast cancer cells, melanoma cells and prostatic cancer cells; and the anti-tumor activity is obviously better than that of a broad-spectrum anti-cancer medicine cis-platinum. In addition, the preparation process of the derivatives is simple, the conditions are mild, the sources of the raw materials are rich, the production cost is low, and potential medicinal value and good application prospectin the aspect of preparing a novel anti-tumor medicine are achieved.

Description

technical field [0001] The invention belongs to the field of medicine, and more specifically relates to a 2,3-dihydro-1H-quinolin-4-one thiosemicarbazone derivative and its preparation method and application. Background technique [0002] Malignant tumor is one of the diseases that seriously threaten human health and life. In 2010, cancer surpassed cardiovascular and cerebrovascular diseases to become the number one killer of human beings. According to statistics, in chemotherapy or combination chemotherapy for malignant tumors, cisplatin drugs are used in the treatment of various solid tumors, such as ovarian cancer, prostate cancer, bladder cancer, rectal cancer, lung cancer, head and neck cancer, etc. However, the structural similarity of cisplatin drugs also makes these drugs have serious drug resistance or cross-resistance in clinical use, which limits the research and development and clinical application of this class of drugs. Therefore, the development of new antit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/42A61P35/00
CPCA61P35/00C07D215/42
Inventor 宋江莉黄通张怡静陈金华莫梓颖宋薇郭俊和
Owner LINGNAN NORMAL UNIV
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