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Fernic acid derivative and its preparation method and application

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: 2021-10-22
SHANGHAI NORMAL UNIVERSITY
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  • Summary
  • 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 postoperative late glaucoma, and believed that Mongolian medicine Mingmu Qiwei Pills combined with Mingmu Xiaoji The treatment of postoperative advanced glaucoma with a short course of treatment and significant curative effect

Method used

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  • Fernic acid derivative and its preparation method and application
  • Fernic acid derivative and its preparation method and application
  • Fernic acid derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] (E)-N,N-Diethyl-5-([1R,4aS,6R,8aS]-6-Hydroxy-5,5,8a-trimethyl-2-methylenedecalin-1- base)-3-methylpent-2-enamide (compound FB1):

[0058] Add 5mL of dichloromethane to dissolve 32mg of fernic acid, add 19mL of diisopropylethylamine, 47mg of condensing agent HATU, and finally add 22mL of diethylamine, mix well and stir at room temperature for 2 hours. After the reaction is complete, add water to terminate the reaction Then it was extracted with dichloromethane, and the dichloromethane phase was rotary evaporated to dryness, separated and purified to obtain the target compound.

[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 H 2 ),3.32(q,J=7.1Hz,2H,a-C H 2 ),3.24(dt,J=10.1,3.9Hz,1H,3-H),2.41(ddd,J=12.8,4.1,2.4Hz,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 H 3 ),1.81-1.48(m,7H,1-H,6-H,2-C H 2 ...

Embodiment 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 of fernic acid in 5mL of dichloromethane, add 19mL of diisopropylethylamine, 47mg of condensing agent HATU, and finally add 12mg of 4-methylpiperidine, mix well and stir at room temperature for 2 hours, after the reaction is complete Water was added to terminate the reaction, and then extracted with dichloromethane. The dichloromethane phase was 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, a-H), 4.52(d, J= 1.6Hz, 1H, 17-H), 3.88(d, J=13.2Hz, 1H, a-H), 3.23(dd, J=12.0, 4.3Hz, 1H, 3-H), 2.95(t, J=12.5Hz ,1H,a-H),2.58(t,J=12.8Hz,1H,a-H),2.40(dd,J=9.3,2.6Hz,1H,7-H),2.22(ddd,J=13.9,9.7,3.8Hz ,1H,12-H),1.98-1.87(m,2H...

Embodiment 3

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

[0068] Dissolve 32mg of fernic acid in 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. After completion, add water to terminate the reaction, then extract with dichloromethane, and rotate the dichloromethane phase to dryness, separate and purify 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,a-H),4.52(s,1H,17-H), 3.96(d, J=13.5Hz, 1H, a-H), 3.23(dd, J=11.7, 4.4Hz, 1H, 3-H), 2.95(t, J=12.8Hz, 1H, a-H), 2.59-2.37( m,7H,a-H,7-H,c-H,2×d-C H 2 ), 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 2,2×b-C H 2 ,c-H,2×e-C H 2...

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Abstract

The present invention relates to fernic acid derivatives and their preparation methods and applications. Fernic acid is used as a substrate to react with various primary or secondary amines under the action of a condensing agent to obtain fernic acid through separation. Derivatives, antibacterial and antitumor cell activity tests were carried out on the synthetic derivatives. The antibacterial results showed that most of the compounds showed antibacterial activity, and the antibacterial activity against Staphylococcus aureus was more obvious; the antitumor results showed that, Most of the compounds showed significant anti-tumor activity, IC for 4 different human cancer cell lines 50 Both are around 10 μM. Compared with the prior art, the synthesis process of the present invention is simple and convenient, and the synthesis efficiency is high, and the compound after separation is high in purity. Fernic acid derivatives are expected to be used in the preparation of antibacterial and antitumor 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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Patent Type & Authority Patents(China)
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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