Alepterolic acid derivative and preparation method and application thereof

A technology for fenback fern acid and derivatives, which is applied in the field of fenback fern acid derivatives and their preparation, can solve the problems of short course of treatment and significant curative effect in advanced glaucoma, and achieves simple and convenient synthesis process, high synthesis efficiency and high purity. Effect

Active Publication Date: 2019-05-28
SHANGHAI NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In modern clinical research, there are few clinical reports on Tongjingcao. Dai Mingshan et al. once observed the therapeutic effect of Mongolian medicine Mingmu Qiwei Pills and Mingmu Xiaoji on 70 patients with postope

Method used

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  • Alepterolic acid derivative and preparation method and application thereof
  • Alepterolic acid derivative and preparation method and application thereof
  • Alepterolic acid derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0056] Example 1

[0057] (E)-N,N-Diethyl-5-([1R,4aS,6R,8aS]-6-hydroxy-5,5,8a-trimethyl-2-methylenedecalin-1- Preparation of 3-methylpent-2-enamide (Compound FB1):

[0058] Dissolve 32mg Pteris acid with 5mL dichloromethane, add 19mL diisopropylethylamine, 47mg condensing agent HATU, and finally add 22mL diethylamine, mix well and stir at room temperature for 2h. After the reaction is complete, add water to terminate the reaction Then it was extracted with dichloromethane, the dichloromethane phase was evaporated to dryness by rotating, and the target compound was obtained by separation and purification.

[0059] The NMR data are as follows: 1 H NMR(500MHz, CDCl 3 )δ5.78-5.74(m,1H,14-H), 4.88-4.84(m,1H,17-H), 4.53(s,1H,17-H),3.46-3.36(m,2H,a-C H2 ), 3.32(q,J=7.1Hz,2H,a-C H2 ), 3.24 (dt, J = 10.1, 3.9 Hz, 1H, 3-H), 2.41 (ddd, J = 12.8, 4.1, 2.4 Hz, 1H, 7-H), 2.23 (ddd, J = 14.0, 9.9, 4.2Hz,1H,12-H),1.95(td,J=14.9,13.6,6.0Hz,2H,7-H,12-H),1.90-1.88(d,J=0.9Hz,3H,16-C H3 ),1.81-1.48(m,7...

Example Embodiment

[0061] Example 2

[0062] (E)-5-([1R,4aS,6R,8aS]-6-hydroxy-5,5,8a-trimethyl-2-methylenedecalin-1-yl)-3-methyl- Preparation of 1-(4-methylpiperazin-1-yl)pent-2-en-1-one (compound FB2):

[0063] Dissolve 32mg Pteris acid with 5mL of dichloromethane, add 19mL of diisopropylethylamine, 47mg of condensation agent HATU, and finally add 12mg of 4-methylpiperidine, mix well and stir at room temperature for 2h, after the reaction is complete The reaction was terminated by adding water and then extracted with dichloromethane. The dichloromethane phase was rotated and evaporated to dryness, and the target compound was obtained by separation and purification.

[0064] The NMR data are as follows: 1 H NMR(500MHz, CDCl 3 )δ5.70(s,1H,14-H), 4.85(d,J=1.6Hz,1H,17-H),4.57(d,J=13.3Hz,1H,aH),4.52(d,J= 1.6Hz, 1H, 17-H), 3.88 (d, J = 13.2Hz, 1H, aH), 3.23 (dd, J = 12.0, 4.3 Hz, 1H, 3-H), 2.95 (t, J = 12.5 Hz ,1H,aH),2.58(t,J=12.8Hz,1H,aH), 2.40(dd,J=9.3,2.6Hz,1H,7-H),2.22(ddd,J=13.9,9.7,3.8Hz ,1H,12-H...

Example Embodiment

[0066] Example 3

[0067] (E)-1-([1,4'-piperidine]-1'-yl)-5-([1R,4aS,6R,8aS]-6-hydroxy-5,5,8a-trimethyl- Preparation of 2-methylene decalin-1-yl)-3-methylpent-2-en-1-one (compound FB4):

[0068] Dissolve 32mg Pteris acid with 5mL of dichloromethane, add 19mL of diisopropylethylamine, 47mg of condensing agent HATU, and finally add 25.3mg of 4-piperidinylpiperidine, mix well and stir at room temperature for 2h, wait for reaction After completion, water was added to terminate the reaction, and then extracted with dichloromethane. The dichloromethane phase was rotated and evaporated to dryness, separated and purified to obtain the target compound.

[0069] The NMR data are as follows: 1 H NMR(500MHz, CDCl 3 )δ5.71(s,1H,14-H), 4.85(s,1H,17-H), 4.67(d,J=12.8Hz,1H,aH), 4.52(s,1H,17-H), 3.96(d,J=13.5Hz,1H,aH), 3.23(dd,J=11.7,4.4Hz,1H,3-H), 2.95(t,J=12.8Hz,1H,aH), 2.59-2.37( m,7H,aH,7-H,cH,2×dC H2 ), 2.22(ddd,J=14.1,9.6,4.1Hz,1H,12-H),1.99-1.33(m,23H,7-H,12-H,1-H,16-CH 3 ,6-CH 2 ,9-H,11-CH...

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Abstract

The invention relates to an alepterolic acid derivative and a preparation method and application thereof. Alepterolic acid serves as a substrate and reacts with various primary amine or secondary amine under the effect of a condensing agent, and the alepterolic acid derivative is obtained through separation; and the synthesized derivative is subjected to antibacterial and anti-tumor cell activitytesting, the antibacterial result shows that most compounds all show bacteriostatic activity and have the more obvious bacteriostatic activity on staphylococcus aureus, and the anti-tumor result showsthat the most compounds show obvious anti-tumor activity, and the IC50 of four types of different human cancer cell lines is all about 10 [mu]M. Compared with the prior art, the synthesizing processis simple and convenient, the synthesizing efficiency is high, the separated compounds are high in purity, the preparation method is an effective way for modifying an alepterolic acid structure to synthesize the new compounds, and the synthesized and prepared alepterolic acid derivative is expected to be applied to the field of preparation of antibacterial and anti-tumor drugs.

Description

technical field [0001] The invention relates to the preparation and application of a compound, in particular to a fernic acid derivative as well as its preparation method and application. Background technique [0002] Silver back fern (Aleuritopteris argentea (Gmél.) Fée), also known as Tongjing grass, copper grass, golden grass, golden bull grass, etc., is a plant of the genus Aleuritopteris argentea in my country, and it is distributed in most parts of China. It is widely used in ethnic minority areas such as Tibetans, Mongolians, and Koreans in my country. For example, Mongolian medicine uses it to treat sores, fractures, pulse and tendon injuries, and irregular menstruation; Tibetan medicine uses it to treat colds, fever, and detoxification; She medicine uses it to treat Irregular menstruation, amenorrhea, tuberculosis hemoptysis, etc. However, its clinical application in traditional Chinese medicine is not much, and it is generally not available in traditional Chinese m...

Claims

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Application Information

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IPC IPC(8): C07C235/30C07C231/24C07D211/16C07D211/58C07D295/185A61P31/04A61P35/00
Inventor 曹建国冯妮平张晟王明龙王全喜黄国正
Owner SHANGHAI NORMAL UNIVERSITY
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