A kind of lycorine β-aryl acrylate derivative and its preparation method and application

A technology of aryl acrylate and lycorine, applied in the field of biomedicine, can solve the problems of large cell damage and exacerbation of the disease, and achieve good anti-tumor application prospects

Active Publication Date: 2022-03-01
SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional tumor treatment uses a combination of radiotherapy and chemotherapy, which causes great damage to normal cells, and patients will experience many adverse reactions in the middle and later stages, which will further aggravate the disease. Therefore, it is urgent to find new tumor treatment targets and develop new tumor treatment drugs. especially important

Method used

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  • A kind of lycorine β-aryl acrylate derivative and its preparation method and application
  • A kind of lycorine β-aryl acrylate derivative and its preparation method and application
  • A kind of lycorine β-aryl acrylate derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1 : 2-tert-butyl dimethyl silicide-stone garlic (INB)

[0098] INB structure:

[0099] Standard (100.0 mmol) and IM (150.0 mmol) were dissolved in 300 ml of DMF in a 2000 ml round bottom reaction flask, and TBSCl (150.0 mmol) was slowly added with vigorous stirring. The temperature rise to 40 ° C for complete dissolved reaction system, after stirring for 4 h, HPLC tracking detects that the starting material stone residual remaining amount is less than 5%. To the reaction system, 500 ml of ethyl acetate and 800 ml of purified water were sequentially added, and the mixture was stirred at room temperature for 10 minutes. Concentrated, column chromatography isolated purified white solid INB. 1 HNMR (500MHz, CDCL 3 Δ6.80 (S, 1H), 6.56 (S, 1H), 5.89 (D, J = 1.1 Hz, 2H), 5.39 (S, 1H), 4.25 (S, 1H), 4.25 (S, 1H), 4.10 (D, J = 14.0 Hz, 1H), 3.45 (D, J = 14.0 Hz, 1H), 3.38-3.25 (M, 1H), 2.78 (D, J = 10.6Hz, 1H), 2.69 (D, J = 10.6Hz, 1H), 2.59 (DD, J = 15.9, 7.9 Hz, 2H), 2.3...

Embodiment 2

[0100] Example 2 : 1- (2-fluoriniacinyl) - stone garine (S1)

[0101] S1 structure:

[0102] A: 250ml round bottom reaction flask INB (10.0 mmol) and 2-fluorinic acid (12.0 mmol) in 50 ml of dichloromethane (12.0 mmol) were dissolved in 50 mL of dichloromethane in room temperature nitrogen. EDCI.HCl (18.0 mmol), DMAP (1.0 mmol) was added sequentially. After completing the reaction at 35 ° C, the HPLC tracking detection INB remaining is less than 8%. The reaction solution was washed once with 100 ml of purified water, 10% sodium chloride solution 100 ml each, and then concentrated under reduced pressure.

[0103] B: 250 ml of round bottom reaction flask was dissolved in 50 ml of anhydrous ethanol, and 5.0 ml of concentrated hydrochloric acid was slowly added dropwise. The reaction was stirred at 80 ° C for 1.0 h, and the heating was closed naturally 50 ° C, 5.0 ml of ammonia water was slowly added dropwise. 80 ml of ethyl acetate and 80 ml of purified water were sequentially adde...

Embodiment 3

[0104] Example 3 : 1- (3-fluoriniacinyl) - stone garine (S2)

[0105] S2 structure:

[0106] A: 250ml round bottom reaction flask INB (10.0 mmol) and 3-fluorinic acid (12.0 mmol) in 50 ml of dichloromethane (12.0 mmol) were dissolved in 50 mm of dichloromethane in room temperature nitrogen. EDCI.HCl (18.0 mmol), DMAP (1.0 mmol) was added sequentially. After completing the reaction at 35 ° C, the HPLC tracking detection INB remaining is less than 8%. The reaction solution was washed once with 100 ml of purified water, 10% sodium chloride solution 100 ml each, and then concentrated under reduced pressure.

[0107] B: 250 ml of round bottom reaction flask was dissolved in 50 ml of anhydrous ethanol, and 5.0 ml of concentrated hydrochloric acid was slowly added dropwise. The reaction was stirred at 80 ° C for 1.0 h, and the heating was closed naturally 50 ° C, 5.0 ml of ammonia water was slowly added dropwise. 80 ml of ethyl acetate and 80 ml of purified water were sequentially adde...

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PUM

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Abstract

The present application provides a derivative of lycorine β-aryl acrylate and its preparation method and application. The lycorine β-aryl acrylate derivative has a structure shown in formula I: wherein, Ar is C 6‑12 Aromatics or C 3‑10 Aromatic heterocycle, the heteroatoms in the aromatic heterocycle are selected from N, O, S; R is a substituent on Ar, which is monosubstituted or multisubstituted, and R is independently selected from hydrogen, halogen, halogenated C 1‑6 Alkyl, halogenated C 1‑6 Alkoxy, nitro, hydroxyl, C 1‑6 Alkyl, C 1‑6 Alkoxy, C 2‑6 Alkenyloxy, C 2‑6 Alkenyl, C 3‑6 Cycloalkyl, phenyl. The lycorine β-aryl acrylate derivative has good anti-tumor activity and has good medicinal prospect.

Description

Technical field [0001] The present application relates to the field of biomedicine, and more particularly to a stone-free beta-aryl methacrylate derivative and a preparation method thereof. Background technique [0002] The information disclosed in the context of the present invention is intended to increase the understanding of the foregoing context of the present application, and the disclosure should not be considered as acknowledgment or in any form that this information has become known to those of ordinary skill in the art. [0003] In recent years, the incidence and mortality of tumors have been rising, and malignant tumors are seriously threatening human health and life safety. According to statistics, more than 1,400,000 people have tumors every year. At present, the current tumor is second in global death. Conventional tumor treatment uses a combination of chemotherapy, which has a large damage to normal cells, and patients will have many adverse reactions in the middle...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/16A61K31/437A61K31/444A61P35/00
CPCC07D491/16A61P35/00Y02P20/55
Inventor 颜世强王鹏曹焕英杨杰何淑旺王文笙景亚军
Owner SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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