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Ellipticine derivatives, drug composition, preparation method and application thereof

A technology of ellipticine and derivatives, applied in the field of medicine, can solve problems such as drug resistance and insensitivity of tumor stem cells

Active Publication Date: 2019-05-14
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional chemotherapy drugs for tumor treatment have drug resistance problems, especially cancer stem cells are less sensitive

Method used

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  • Ellipticine derivatives, drug composition, preparation method and application thereof
  • Ellipticine derivatives, drug composition, preparation method and application thereof
  • Ellipticine derivatives, drug composition, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] 9,15-Dimethyl-15b,16-dihydroquinazolino[3',2':1,2]pyrido[4,3-b]carbazol-5(10H)-one

[0085] 9,15-Dimethyl-15b,16-dihydroquinazolino[3’,2’:1,2]pyrido[4,3-b]carbazol-5(10H)-one

[0086]

[0087] Dissolve 25 mg (0.1 mmol) of ellipticine and 27 mg (0.2 mmol) of 2-aminobenzoic acid in 3 ml of anhydrous N,N-dimethylformamide, and add 38 mg (0.2 mmol) of 1-ethyl-(3- Dimethylaminopropyl) carbodiimide hydrochloride (EDCI), reacted at room temperature for 5 hours, a yellow solid precipitated, and TLC monitoring showed that the reaction was complete. After concentration, the residue was extracted with dichloromethane (20 mL×3), and the combined organic phases were sequentially washed with saturated sodium bicarbonate solution, purified water and saturated sodium chloride solution, and dried overnight over anhydrous sodium sulfate. After evaporating dichloromethane, the obtained yellow solid was treated with absolute ethanol to obtain 20 mg of a yellow solid product with a yiel...

Embodiment 2

[0089] 3,9,15-Trimethyl-15b,16-dihydroquinazolino[3',2':1,2]pyrido[4,3-b]carbazol-5(10H)-on e

[0090] 3,9,15-Trimethyl-15b,16-dihydroquinazolino[3’,2’:1,2]pyrido[4,3-b]carbazol-5(10H)-one

[0091]

[0092] Dissolve 25 mg (0.1 mmol) of ellipticine and 30 mg (0.2 mmol) of 2-amino-5-methylbenzoic acid in 3 ml of anhydrous N,N-dimethylformamide, add 38 mg (0.2 mmol) of EDCI, and After 5 hours of reaction, a yellow solid precipitated out, and TLC monitoring showed that the reaction was complete. After concentration, the residue was extracted with dichloromethane (20 mL×3), and the combined organic phases were sequentially washed with saturated sodium bicarbonate solution, purified water and saturated sodium chloride solution, and dried overnight over anhydrous sodium sulfate. After evaporating dichloromethane, the obtained yellow solid was treated with absolute ethanol to obtain 24 mg of a yellow solid product with a yield of 63.3%. 1 H NMR (500MHz, DMSO-d 6)δ11.30(s,1H,N-H)...

Embodiment 3

[0094] 4,9,15-Trimethyl-15b,16-dihydroquinazolino[3',2':1,2]pyrido[4,3-b]carbazol-5(10H)-one

[0095] 4,9,15-Trimethyl-15b,16-dihydroquinazolino[3’,2’:1,2]pyrido[4,3-b]carbazol-5(10H)-one

[0096]

[0097] Dissolve 25mg (0.1mmol) of ellipticine and 30mg (0.2mmol) of 2-amino-6-methylbenzoic acid in 3ml of anhydrous N,N-dimethylformamide, add 38mg (0.2mmol) of EDCI, and After 5 hours of reaction, a yellow solid precipitated out, and TLC monitoring showed that the reaction was complete. After concentration, the residue was extracted with dichloromethane (20 mL×3), and the combined organic phases were sequentially washed with saturated sodium bicarbonate solution, purified water and saturated sodium chloride solution, and dried overnight over anhydrous sodium sulfate. After evaporating dichloromethane, the obtained yellow solid was treated with absolute ethanol to obtain 17 mg of a yellow solid product with a yield of 44.9%. 1 H NMR (500MHz, DMSO-d 6 )δ11.27(s, 1H, N-H), 8.1...

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Abstract

The invention relates to ellipticine derivatives shown as formulas (I, II, III and IV) or pharmaceutically acceptable salt thereof. The derivatives have excellent antitumor activity, little side effect, low toxicity and / or high dissolubility in water and can serve as an antitumor agent and an antiviral agent. The invention further relates to a preparation method, a drug composition and applicationof the ellipticine derivatives.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a new class of ellipticine derivatives, a pharmaceutical composition containing them, and their application in the preparation of antitumor and antiviral drugs. Background technique [0002] In the past 30 years, although various diagnosis and treatment levels of tumors have been significantly improved, the morbidity and mortality of tumors are still increasing worldwide. According to the forecast of the World Health Organization (WHO), by 2020, the number of cancer cases worldwide will increase to 20 million, and the death toll will reach 12 million. [1] . In 2015, 8.2 million people died of cancer worldwide, including 2.8 million in China. Now 7,500 people die of cancer every day in China. China has the highest number of cancer deaths in the world. In China, the prevalence of cancer is 280 per 100,000, showing a trend of rapid growth year by year [2] . The ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/14C07D495/22A61K31/519A61P35/00A61P35/02A61P31/16A61P31/22A61P31/14A61P31/20
CPCY02A50/30
Inventor 潘显道李燕林菁菁沈珑瑛杨亚军郑稳生
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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