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Genipin derivative and application thereof in preparing drug for preventing and treating neurodegenerative disease

A kind of methyl genipin and pharmaceutical technology, applied in the field of medicine, can solve the problems of poor blood-brain barrier permeability and bioavailability, limited pharmacological effects, low fat solubility, etc., achieve significant nerve cell protection activity, enhance cell Vitality, high fat-soluble effect

Active Publication Date: 2017-06-13
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the influence of C-3, C-10 hydroxyl and hemiacetal in the parent structure of genipin, it has poor stability in physiological solution, low fat solubility, blood-brain barrier permeability and bioavailability Poor, limiting its pharmacological effects

Method used

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  • Genipin derivative and application thereof in preparing drug for preventing and treating neurodegenerative disease
  • Genipin derivative and application thereof in preparing drug for preventing and treating neurodegenerative disease
  • Genipin derivative and application thereof in preparing drug for preventing and treating neurodegenerative disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Preparation of compound G1. The genipin compound reacts with isopropanol under the catalysis of boron trifluoride ether to generate isopropoxygenipin. The obtained isopropoxygenipin (0.5mmol) was dissolved in 10ml of anhydrous dichloromethane, and the amount of benzoic acid equal to that of the substance was added, and after dissolving, 5mg of 4-dimethylaminopyridine (DMAP) was added, and 920mg of bicyclic Hexylcarbodiimide (DCC), stirred at room temperature, monitored by TLC. After the reaction was completed, it was filtered, separated by silica gel column chromatography (eluted with petroleum ether-ethyl acetate), and the solvent was removed under reduced pressure to obtain compound G1. Molecular formula(MW):C 21 h 24 o 6 (372.41g / mol); white oil; 63.0% Yield; 1 H NMR (600MHz, CDCl 3 )δ1.22(3H,d,J=6.14Hz),1.29(3H,d,J=6.21Hz),2.10(1H,m),2.66(1H,t,J=8.25Hz),2.92(1H, dd,J=16.57,8.56Hz),3.24(1H,q,J=8.36Hz),3.73(3H,s),4.06(1H,m),4.66(1H,d,J=8.35Hz),4.92( ...

Embodiment 2

[0054] Embodiment 2: Compound G2, Molecular formula (MW): C 22 h 26 o 6 (386.44g / mol); lightwhite oil; 72.0% Yield; 1 H NMR (600MHz, DMSO-d 6 )δ1.01(3H,d,J=6.09Hz),1.05(3H,d,J=6.18Hz),2.15(1H,m),2.52(3H,s),2.67(1H,dd,J=15.24 ,6.66Hz),3.02(2H,m),3.64(3H,s),3.84(1H,m),4.87(2H,q,J=7.56Hz),5.39(1H,d,J=3.06Hz), 5.93(1H,s),7.32(2H,m),7.44(1H,d,J=1.07Hz),7.49(1H,td,J=7.66,1.25Hz),7.87(1H,d,J=7.81Hz ); 13 C-NMR (150MHz, DMSO-d 6 )δ21.01,21.26,23.05,33.69,38.42,45.73,50.90,62.14,70.34,96.66,110.68,125.92,129.36,130.07,131.32,131.55,132.10,136.81,139.07,151.17,166.56,166.92;ESI-MS (m / z):387.1([M+H] + ).

Embodiment 3

[0055] Embodiment 3: Compound G3, Molecular formula (MW): C 22 h 26 o 6 (386.44g / mol); lightwhite oil; 70.0% Yield; 1 H NMR (600MHz, CDCl 3 )δ1.14(3H,d,J=6.11Hz),1.18(3H,d,J=6.19Hz),2.10(1H,m),2.39(3H,s),2.62(1H,t,J=8.18 Hz), 2.76(1H,dd,J=16.01,8.15Hz),3.08(1H,q,J=8.54Hz),3.65(3H,s),4.02(1H,m),4.80(1H,d,J =8.09Hz), 4.85(1H,d,J=12.74Hz),4.99(1H,d,J=14.25Hz),5.93(1H,s),7.34(2H,d,J=8.02Hz),7.52( 1H, d, J = 0.74Hz), 7.90 (2H, d, J = 8.17Hz); 13 C-NMR (150MHz, CDCl 3)δ21.08, 21.47, 23.23, 35.34, 38.36, 45.90, 50.94, 62.42, 71.52, 99.55, 110.06, 126.85, 129.19, 129.25, 138.36, 143.62, 152.19, 165.26, 166.86 387.1([M+H] + ).

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Abstract

The invention discloses novel medicinal use of a genipin derivative and in particular to an application thereof in preparing a drug for preventing and treating neurodegenerative disease. The genipin derivative is as shown in a structural formula (I). Verified by an H2O2 induced PC12 cell oxidative damage model and a PD animal model test, the genipin derivative has an obvious neuroprotective effect and has an important application prospect in preparing the drug related to prevention and treatment of neurodegenerative disease.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to a class of geni derivatives and their application in the preparation of drugs for preventing and treating neurodegenerative diseases. Background technique [0002] With the intensification of population aging, neurodegenerative diseases have become the diseases with the highest incidence among middle-aged and elderly people, which not only bring great pain to patients themselves, but also cause serious economic and mental burdens to families and society. Neurodegenerative diseases are disease states in which cells and neurons of the brain and spinal cord are lost. Representative diseases include Alzheimer's disease, Parkinson's syndrome, multiple sclerosis, etc., and their pathogenesis has not been elucidated so far. At present, there are many kinds of clinical drugs used in the prevention and treatment of neurodegenerative diseases, including dopamine-mimetic drugs, central cholinergic r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/94A61K31/352A61P25/16A61P25/28A61P25/14A61P25/00
CPCC07D311/94
Inventor 李青山梁泰刚苗俊秋陈景润崔东晓闫超群韩玲革
Owner SHANXI MEDICAL UNIV
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