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1-O-alkyl genipin and preparation method and application thereof

A technology of alkyl genipin and genipin, applied in nervous system diseases, organic chemistry, drug combination, etc., can solve the problem of weak activity of genipin derivatives

Active Publication Date: 2021-12-24
SHAANXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Moreover, a large number of experimental studies have found that 1R-substituted genipin derivatives have better neuroprotective activity, and 1S-substituted genipin derivatives have weaker activity
However, the C1 substituted genipin derivatives prepared in the prior art are all racemates of R / S configuration

Method used

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  • 1-O-alkyl genipin and preparation method and application thereof
  • 1-O-alkyl genipin and preparation method and application thereof
  • 1-O-alkyl genipin and preparation method and application thereof

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preparation example Construction

[0040] The invention provides a kind of preparation method of 1-O-alkylgenipin, comprises the following steps:

[0041] Mix raw material A, lower carbon alcohol, Lewis acid catalyst and polar organic solvent (hereinafter referred to as the first polar organic solvent) to carry out alkoxylation reaction to obtain 1-O-alkyl genipin, and the raw material A includes jing Nepin and / or 10-O-Piv-1-O-NHCl 3 Genipin, the 10-O-Piv-1-O-NHCl 3 Genipin is shown in formula I:

[0042]

[0043] In the present invention, unless otherwise specified, the raw materials used are commercially available products well known to those skilled in the art.

[0044] In the present invention, the raw material A includes genipin and / or 10-O-Piv-1-O-NHCCl 3 Genipin, more preferably comprising genipin or 10-O-Piv-1-O-NHCl 3 Genipin.

[0045] In the present invention, the 10-O-Piv-1-O-NHCCl 3 The preparation method of genipin preferably comprises the following steps:

[0046] 10-O-Piv-genipin of str...

Embodiment 1

[0114] In a 50mL round bottom flask, add genipin 0.2g (0.88mmol), methanol (2.65mmol), Molecular sieves (0.05g) and 10mL DMC were slowly added dropwise (pseudo-dropping speed 0.5mL / min) boron trifluoride diethyl ether (0.15mL, 1.33mmol) into the reaction system under the protection of nitrogen, and at -30°C, After reacting for 8h hours, the reaction system was poured into 50mL ice water to quench, and extracted 3 times with dichloromethane, each time the amount of dichloromethane was 50ml), and the combined organic phase after 3 extractions was washed with 100mL saturated brine to Neutral, with anhydrous Na 2 SO 4 After drying, it was concentrated under reduced pressure, and purified by silica gel column chromatography (the eluent was a mixed solvent of ethyl acetate and petroleum ether, and the volume ratio of the two was 1:3) to obtain a light yellow oil, which was 1-O-methyl Genipin, NMR spectrum such as figure 1 shown.

Embodiment 2～14

[0116] Embodiment 1~14 implementation process is identical with embodiment 1, and the kind of reaction raw material, reaction temperature, polar organic solvent that embodiment 1~14 uses is listed in table 1, and the 1-O-alkane that embodiment 1~14 obtains The isolated yield of genipin, the molar ratio of 1S-O-alkylgenipin and 1R-O-alkylgenipin ( c1H-NMR determination) are listed in Table 1.

[0117] The reaction equation among the embodiment 1~14 is shown in formula V:

[0118]

[0119] The reaction condition parameter and the result of table 1 embodiment 1~14

[0120]

[0121]

[0122] The 1-O-methylgenipin of embodiment 1~8 preparation 1 H-NMR is:

[0123] 1-O-Methylgenipin: 1 H-NMR (CDCl 3 )δ:2.05-2.26(2H,m),2.59-2.63(2H,m),2.74-2.92(2H,m),3.04-3.23(2H,m),3.43(3H,s),3.59(3H, s),3.73(3H,s),4.19(1H,d,J=13.2Hz),4.25(2H,s),4.26(1H,d,J=13.2Hz),4.49(1H,d,J=8.0 Hz), 5.07(1H,d,J=3.2Hz), 5.80(1H,s), 5.84(1H,s), 7.46(1H,s), 7.52(1H,s).

[0124] Implementation of 1-O...

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Abstract

The invention belongs to the technical field of genipin derivative synthesis, and particularly relates to 1-O-alkyl genipin and a preparation method and application thereof. The invention provides the preparation method of 1-O-alkyl genipin, the preparation method comprises the following steps: mixing a raw material A, low-carbon alcohol, a Lewis acid catalyst and a polar organic solvent, and carrying out an alkoxylation reaction to obtain 1-O-alkyl genipin, the raw material A comprising genipin and / or 10-O-Piv-1-O-NHCCl3 genipin. In the 1-O-alkyl genipin obtained by the preparation method, the conformation of the 1R-O-alkyl genipin is dominant, and the neuroprotective activity is higher.

Description

technical field [0001] The invention belongs to the technical field of synthesis of genipin derivatives, and in particular relates to a 1-O-alkyl genipin and its preparation method and application. Background technique [0002] Genipin has anti-hypertensive, anti-inflammatory, anti-tumor, anti-thrombosis, anti-pathogen, protective nerve cells and other effects. [0003] Nerve cells have a great demand for oxygen, but the anti-oxidation mechanism is relatively weak, so reactive oxygen species and reactive nitrogen can indirectly cause nerve cell death. Genipin exhibits excellent neurogenic protective activity, based on the structure and electronic properties of genipin, Hughes (Neuroprotection by genipin against reactive oxygen and reactive nitrogen species-mediated injury in organotypic hippocampal slicecultures[J].Brain.Res.,2014 , 1543(2):308-314) et al. studied the ability of genipin to reduce the damage of reactive oxygen species and reactive nitrogen to nerve cells thr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/94A61P25/00
CPCC07D311/94A61P25/00Y02P20/55
Inventor 史永恒韩朝军王川史海龙王斌刘继平
Owner SHAANXI UNIV OF CHINESE MEDICINE
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