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Senecio scandens derivative and application thereof in drugs

A derivative, sensible technology, applied in the direction of organic chemistry, organic chemical methods, antiviral agents, etc., can solve problems such as easy to cause asthma and chronic obstructive pneumonia, use restrictions, etc.

Active Publication Date: 2018-05-29
湖南天济草堂制药股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because of the way it is taken, its use is limited and it can easily cause asthma and chronic obstructive pneumonia
The second commercially developed drug of this type is oseltamivir phosphate, which is taken orally. It is produced and developed by Roche, and its Chinese name is "Tamiflu". Finally, influenza virus is prone to develop drug resistance to Tamiflu. At present, seeking new anti-influenza drugs with less side effects and high bioavailability has become an urgent problem to be solved.

Method used

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  • Senecio scandens derivative and application thereof in drugs
  • Senecio scandens derivative and application thereof in drugs
  • Senecio scandens derivative and application thereof in drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1S, 3S, 4R, 5R)-3-amino-1,4-dihydroxy-5-(((E)-3-(3-hydroxy-4-propoxyphenyl)acryloyl)oxy) The synthesis of cyclohexanecarboxylic acid comprises the following steps:

[0034] Synthesis of S1, 3-methoxy-4-n-propoxybenzaldehyde: 4-hydroxyl-3-methoxybenzaldehyde (15.2g, 100mmol) was dissolved in 300mL of DMF, bromopropane (13.4 g, 110mmol) and K 2 CO 3 (15.2 g, 110 mmol). After the reaction solution was reacted at 100° C. for 6 hours, TLC (PE:EA=2:1) ​​monitored that the reaction was complete. The reaction solution was poured into water (500 mL), and extracted with ethyl acetate (500 mL×3). The combined reactions were sequentially washed with saturated NH 4 Cl aqueous solution (500mL×3), water (300mL) and saturated brine (300mL) were washed, dried over anhydrous sodium sulfate, filtered, and concentrated to give a yellow oily product (15.3g, 79%);

[0035] S2. Synthesis of (E)-3-(3-methoxy-4-propoxyphenyl)ethyl acrylate: NaH (0.26g, 11mmol) was dissolved in 20mL of TH...

Embodiment 2

[0053] (1S, 3S, 4R, 5R)-3-amino-1,4-dihydroxy-5-(((E)-3-(3,4-di-hydroxyphenyl)acryloyl)oxy)cyclohexyl For the synthesis of alkanoic acid, referring to Example 1, TJB-002 was obtained by using 3,4-dihydroxybenzaldehyde as the starting material.

[0054] MS(ESI,pos.ion)m / z:380(M+1);

[0055] 1 H NMR (400MHz, DMSO-d 6 )δ(ppm): 10.5(s,1H), 7.48(s,1H), 6.89-7.25(m,3H), 6.31(s,1H), 5.33(s,1H), 5.12(dd,J=11.2 ,2H), 43(t,J=7.2Hz,2H),4.05(m,4H),3.58(S,1H),3.55(s,1H),1.93-2.65(m,5H);

[0056] 13 C NMR (101MHz, DMSO-d 6 )δ (ppm): 177.44, 167.04, 149.60, 146.23, 143.2, 128.6, 123.6, 116.8, 114.6, 112.5, 81.5, 79.4, 68.9, 64.4, 64.4, 47.5, 38.3, 35.6.

Embodiment 3

[0058] (1S, 4R, 5S)-3-amino-5-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4-dihydroxycyclohexanecarboxylic acid Synthesis Referring to Example 1, TJB-003 was prepared by using 3,4-dimethoxybenzaldehyde as the starting material.

[0059] MS(ESI,pos.ion)m / z:354(M+1);

[0060] 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 10.5 (s, 1H), 7.48 (s, 1H), 6.82-7.28 (m, 3H), 6.36 (s, 1H), 5.38 (s, 1H), 5.15 (dd, J = 11.2 ,2H), 4.01(m,2H), 3.58(S,1H), 3.66(s,1H), 1.73-2.68(m,5H);

[0061] 13 C NMR (101MHz, DMSO-d 6 )δ (ppm): 176.54, 166.14, 149.20, 147.26, 144.3, 127.7, 122.7, 116.7, 114.6, 112.3, 81.6, 79.1, 68.4, 47.5, 38.3, 35.6.

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Abstract

The invention discloses a senecio scandens derivative and application thereof in drugs. The enecio scandens derivative is the derivative of the effective component chlorogenic acid of senecio scandens. The derivative of the chlorogenic acid is a compound as shown in chemical generation formula I, II, III or IV or one or the combination of the stereisomer, geometrical isomer, tautomer, solvate, polymorphic substance, metabolite, ester, pharmaceutically acceptable salt, prodrug, pharmaceutically acceptable prodrug salt, pharmaceutically acceptable carrier, excipient, diluent, adjuvant and intermedium of the compound. The senecio scandens derivative is used for preparing antiviral drugs. The senecio scandens derivative is good in solubility, high in purity, good in antipyretic performance andespecially suitable for being used as the effective component to prepare antipyretic, anti-inflammation and antibacterial drugs.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and in particular relates to a senecio derivative and its application in medicine. Background technique [0002] The sudden new viral infectious disease is a kind of highly contagious and harmful disease caused by the evolution or mutation of the virus itself. Because the pathogen is a new biological structure, there is often no effective prevention and control means when it breaks out, resulting in hazards are extremely serious. Due to its high variability and susceptibility to the human body, influenza virus has become an important source of sudden new viral diseases. Every once in a while, new influenza will become a pandemic in humans, and there have been at least four outbreaks in the past 100 years. The 1918 influenza pandemic claimed the lives of nearly 20 million people worldwide. Especially the SARS that broke out in South my country in 2003 and the global swine flu virus disease cause...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/48C07C233/52C07D319/20C07C69/732C07C69/736A61P31/16
CPCC07B2200/07C07C69/732C07C69/736C07C229/48C07C233/52C07D319/20
Inventor 关启明李林梅
Owner 湖南天济草堂制药股份有限公司
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