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Split-ring lupinane derivatives and medicinal application thereof

A technology of lupinane and derivatives is applied in the field of split-ring lupinane derivatives and pharmaceutical compositions containing them, and can solve the problems of shortening sleep latency and the like

Inactive Publication Date: 2017-12-22
JILIN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The melatonin receptor agonist ramelteon (ramelteon), which was first listed in the United States in 2005, is used for the treatment of insomnia, which can shorten the sleep latency, improve sleep efficiency and sleep maintenance. Compared with traditional drugs, this drug does not damage the Cognitive activity on the next day, no withdrawal symptoms; but this drug has mild side effects, such as headache, fatigue, lethargy, etc. (Arendt J, Van Someren EJ, Appleton R, et a1.Clinical update: melatonin and sleep disorders. Clin Med, 2008, 8(4): 381-383)

Method used

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  • Split-ring lupinane derivatives and medicinal application thereof
  • Split-ring lupinane derivatives and medicinal application thereof
  • Split-ring lupinane derivatives and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Synthesis of split ring lupin derivatives

[0029] 1.1 Instruments and reagents

[0030] 1 HNMR nuclear magnetic resonance spectrum adopts Bruker AVII 500 superconducting nuclear magnetic resonance instrument; HRMS mass spectrometry adopts UPLC-XevoG 2 -S QTOF-MS / MS. Derivative 1 is self-made in the laboratory (purity ≥ 98%), and other reagents are domestic analytical reagents.

[0031] 1.2 Synthesis of derivatives

[0032] 1.2.1 Synthesis of Derivative 2

[0033] Dissolve derivative 1 (484.0mg, 1.0mmol) in 50mL of dichloromethane, add vanadyl acetylacetonate (26.0mg, 0.1mmol), stir well and add 70% tert-butyl hydroperoxide aqueous solution (413μL, 3mmol) , react at room temperature for 3 hours, add 30mL aqueous sodium bicarbonate solution, stir for 15 minutes, extract 3 times with ethyl acetate 30mL, combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, and recover the solvent under reduced pressure to obtain derivati...

Embodiment 2

[0065] Example 2: Test of melatonin receptor agonistic activity of split-lupin derivatives

[0066] 2.1 Method: Homogeneous Time-Resolved Fluorescence Method (Zhang Xuan. New synthesis method and structural transformation of melatonin receptor agonist ramelteon and design and synthesis of single-molecule multi-target anti-tumor drugs[D]. East China Normal University University, 2014.).

[0067] 2.2 Results: According to the results obtained by the above method, the prepared split-lupin derivatives 1-10, 1a-4a showed certain activities against MT1 and MT2, as shown in Table 1.

[0068] Table 1 EC of split ring lupin derivatives 50 Value (nM)

[0069]

[0070] 2.3 Conclusion: The prepared split ring lupine derivatives 1-10, 1a-4a have certain activities on MT1 and MT2, and have the potential to prevent, slow down or treat diseases related to central nervous system dysfunction. Potential drug development value.

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Abstract

The invention relates to split-ring lupinane derivatives, a medicinal composition containing the split-ring lupinane derivative and application of the split-ring lupinane derivatives in the preparation of medicine for prevention, treatment or slow-down of diseases of the central nervous system related to agonism of melatonin receptors. In the invention, through a semi-synthesis method, the structural limitation of natural products in the prior art is changed, a series of split-ring lupinane derivatives is designed and synthesized, and the agonist activity of the split-ring lupinane derivatives over the melatonin receptor in vitro is verified; through further experiments, the split-ring lupinane derivative compound can be applied to the research of the medicine for the treatment of the diseases related to a dysfunction of the central nervous system.

Description

technical field [0001] The invention belongs to the field of medicines, and in particular relates to a class of split ring lupine derivatives, pharmaceutical compositions containing them and their therapeutic use in diseases related to central nervous system dysfunction. More specifically, the present invention describes split-lupene derivatives that can be used as melatonin receptor agonists. Background technique [0002] Melatonin is a neuroendocrine hormone secreted by the pineal gland. Melatonin was first recognized for its ability to regulate seasonal and circadian rhythms. However, with the deepening of research, it is found that it also has various physiological functions such as sedation, hypnosis, analgesia, anti-depression, anti-convulsion, regulation of immune response, delaying aging and regulating the growth and development of the reproductive system. Melatonin has efficient free radical scavenging ability, can scavenge a variety of free radicals in the body, ...

Claims

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Application Information

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IPC IPC(8): C07J71/00C07J1/00C07J17/00A61K31/565A61K31/585A61K31/7032A61P25/00A61P25/20A61P25/22A61P25/24A61P25/18A61P25/16A61P25/14A61P25/28A61P25/06A61P25/08
CPCC07J71/0005C07J1/00C07J17/005
Inventor 赵岩郭雪边兴博陈晨王伟东付天华尹永霞
Owner JILIN AGRICULTURAL UNIV
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