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Bisabolane sesquiterpene analogue, and preparation method and application thereof

A drug and reaction technology, used in pharmaceutical formulations, drug combinations, anti-tumor drugs, etc., can solve problems such as toxicity and achieve the effect of inhibiting proliferation

Active Publication Date: 2017-07-28
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main defect of existing anticancer drugs is that they have different degrees of toxicity to normal cells, which are closely related to various side effects of anticancer drugs such as bone marrow suppression, gastrointestinal toxicity, anemia and alopecia

Method used

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  • Bisabolane sesquiterpene analogue, and preparation method and application thereof
  • Bisabolane sesquiterpene analogue, and preparation method and application thereof
  • Bisabolane sesquiterpene analogue, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1, the preparation of formula I compound

[0049] in N 2Under protection, add 4-bromo-2-thiophenecarbaldehyde (382.1mg, 2.0mmol), p-cyanophenylboronic acid (353mg, 2.4mmol) and 1,4-dioxane (20mL) into a 50mL three-necked reaction flask After stirring and dissolving, cesium carbonate (1629.1mg, 5.0mmol) and water (10mL) were added, and stirring was continued for 5min at room temperature, and tetrakistriphenylphosphine palladium (115.6mg, 0.1mmol) was added to the reaction system. 2 Under protection, the reaction was continued under reflux for 6h. After the reaction solution was cooled to room temperature, dichloromethane (20 mL) was added and the layers were separated. The aqueous layer was extracted with dichloromethane (2×10 mL). The organic phases were combined and dried overnight over anhydrous sodium sulfate. After filtration, the solvent was evaporated to dryness under reduced pressure to obtain a crude product, which was separated by silica gel column...

Embodiment 2

[0054] Embodiment 2, the effect of the compound shown in formula I on the proliferation and growth of tumor cells

[0055] Construction of cell screening models: breast cancer cells (MCF-7), cervical cancer cells (HeLa), ovarian cancer cells (HO8910), lung cancer cells (A549), bladder cancer cells (T24), gastric cancer cells (BGC-823) and small Mouse embryonic fibroblasts (NIH 3T3) were purchased from the Basic Medical Cell Center, Institute of Basic Medical Sciences, Chinese Academy of Medical Sciences.

[0056] MTT method (MTT colorimetric method) was used to test the effect of the compound shown in formula I prepared in Example 1 on the proliferation and growth of the above six tumor cells and NIH 3T3 cells. In order to verify the dose-response of several tumor cells to the compound, the compound shown in formula I prepared in Example 1 and the positive control drug cisplatin all use DMSO (dimethyl sulfoxide, Dimethyl sulfoxide, DMSO) as a solvent to prepare a concentration...

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Abstract

The invention discloses a bisabolane sesquiterpene analogue, and a preparation method and application thereof. The bisabolane sesquiterpene analogue provided by the invention has a structural formula as shown in a formula I. The preparation method for the bisabolane sesquiterpene analogue as shown in the formula I comprises the following steps: 1) subjecting 4-bromo-2-thiophenecarboxaldehyde and p-cyanophenylboric acid to the Suzuki coupling reaction so as to obtain a compound as shown in a formula II; (2) subjecting the compound as shown in the formula II and methylmalonic acid to the Knoevenagel condensation reaction so as to obtain a compound as shown in a formula III; and (3) subjecting ammonia water and a reaction product of the compound as shown in the formula III with thionyl chloride to a reaction an ice bath so as to obtain the compound as shown in the formula I. The compound as shown in the formula I or a pharmaceutically acceptable salt thereof provided by the invention is applicable to preparation of anti-tumor drugs. The anti-tumor drugs can inhibit propagation of tumor cells like breast cancer cells, cervical cancer cells and / or ovarian carcinoma cells; and specifically, the breast cancer cells may be MCF-7 cells, the cervical cancer cells may be HeLa cells, and the ovarian carcinoma cells may be HO8910 cells.

Description

technical field [0001] The invention relates to a myrrh alkyl sesquiterpene structural analogue and a preparation method and application thereof, belonging to the field of medicine. Background technique [0002] Malignant tumors are the main killers that threaten human health, and there is still a lack of efficient and safe drugs. The main defect of existing antineoplastic drugs is that they have varying degrees of toxicity to normal cells, which are closely related to various side effects of antineoplastic drugs such as bone marrow suppression, gastrointestinal toxicity, anemia and alopecia. Therefore, the research and development of selective anti-tumor compounds that are effective on tumor cells and do not affect normal cells have important application value. [0003] Researchers have discovered a series of new structures of bisabolane and bergamotane sesquiterpenes from the fermentation product of the endophytic fungus Paraconiothyrium brasiliense [see, European Journal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24A61K31/381A61P35/00
CPCC07D333/24
Inventor 车永胜张杨王勃张着伟
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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