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Derivatives of berberine dimer analog jja-d0 or pharmaceutically acceptable salts, preparation methods and uses thereof

A technology of JJA-D0 and berberine, which is applied in the field of medicine, can solve the problem of a single modifiable site of the parent compound, achieve the effects of inhibiting NADPH oxidase, simple preparation process, and low cost

Active Publication Date: 2021-06-11
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the previous work, the berberine dimer has been synthesized in the prior art and is ready to be structurally modified, but the modified site of this parent compound is relatively single

Method used

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  • Derivatives of berberine dimer analog jja-d0 or pharmaceutically acceptable salts, preparation methods and uses thereof
  • Derivatives of berberine dimer analog jja-d0 or pharmaceutically acceptable salts, preparation methods and uses thereof
  • Derivatives of berberine dimer analog jja-d0 or pharmaceutically acceptable salts, preparation methods and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1: Compound Apo-NO 2 Synthesis

[0086] Take berberine (1.66g, 10mmol), add 10ml of glacial acetic acid to dissolve, slowly add 1.5ml of 67wt% concentrated nitric acid under ice bath stirring, react for 30min, remove ice water, react at room temperature for 3h, add to the system after the reaction Ice-water, suction-filtered to obtain a yellow solid, washed with ice-water, and recrystallized in 95% (v / v) ethanol to obtain yellow needle-like crystals (1.65 g, yield 78%). This compound is a known compound, which is consistent with the spectra recorded in the literature through mass spectrometry and nuclear magnetic spectrum.

Embodiment 2

[0087] Embodiment 2: Compound Apo-NH 2 Synthesis

[0088] Apo-NO 2 (2.11g, 10mmol) was dissolved in 30ml ethanol, and the mass ratio was added to be 10% Pd / C (950mg), and the reaction mixture was passed into H 2 Reacted overnight, washed with water after the reaction, took the organic layer and concentrated it under reduced pressure, and separated it on a silica gel column (ethyl acetate:petroleum ether=1:2) to obtain a light white solid Apo-NH 2 (1.32 g, 73% yield). This compound is a known compound, which is consistent with the spectra recorded in the literature through mass spectrometry and nuclear magnetic spectrum.

Embodiment 3

[0089] Embodiment 3: the synthesis of compound Apo-CHO

[0090] Put berberine (1.66g, 10mmol) in a flask, add a mixed solution of 3ml of triethylamine and 20ml of absolute ethanol, then drop 30ml of 50wt% sodium hydroxide aqueous solution into the system, stir and mix. Chloroform (5.95g, 50mmol) was added dropwise to the reaction solution, and reacted at 70-80°C for 2h. The reaction solution was cooled to room temperature and acidified to pH=1 with hydrochloric acid. The organic layer was collected, the aqueous layer was extracted with dichloromethane, the organic layers were combined and washed with water, dried over anhydrous sodium sulfate, concentrated, and separated on a silica gel column (ethyl acetate:petroleum ether=2:3) to obtain a light yellow powder Apo-CHO (0.69 g, 36% yield). This compound is a known compound, which is consistent with the spectra recorded in the literature through mass spectrometry and nuclear magnetic spectrum.

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Abstract

The present invention relates to derivatives of berberine dimer analog JJA-D0 or pharmaceutically acceptable salts, preparation methods and uses thereof. The compound has the structure of general formula (I). The present invention introduces hydrocarbon groups, aryl groups, heteroaryl groups, alkoxycarbonyl groups, acyl groups, sulfonate groups, antioxidant groups such as lipoic acid groups, H 2 S donor groups such as cysteinyl, NO donor groups such as nitrate groups, etc., synthesized and disclosed a series of compounds with new structures. These compounds can inhibit NADPH oxidase, and have a better anti-oxidation and anti-inflammatory dual pharmacological mechanism than berberine. Some of these compounds can also provide NO, H 2 The donor group of S can further enhance the pharmacological activity, and it is a new class of multifunctional compound. The disclosed JJA-D0 derivatives can be used to prevent or treat diseases related to NADPH oxidase, diseases related to free radicals, diseases related to inflammation, diseases related to NO, diseases related to H 2 Preparation of health products or medicines for S-related diseases.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to derivatives of berberine dimer analog JJA-D0 or pharmaceutically acceptable salts thereof, preparation methods and applications. Background technique [0002] Berberine is the main active ingredient in Hu Huanglian, a commonly used traditional Chinese medicine. It was originally isolated from Apocynum Cannabinum L., and its structure is shown below. Huhuanglian is the rhizome of Tibet Huhuanglian and Huhuanglian, which are plants of the family Scrophulariaceae. Huhuanglian is mainly distributed in the Himalayas, and Tibetan Huhuanglian is mainly distributed in Sichuan, Yunnan, and Tibet. [0003] [0004] Molecular structure of berberine [0005] Huhuanglian is used in Indian folk for the treatment of gallbladder, antimalarial, spleen, urinary tract infection and hepatitis. With the in-depth study of its chemical components and pharmacological effects, it was found that ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/22C07C221/00C07D339/04C07C321/14C07C319/20C07C233/33C07C231/12C07C309/66C07C303/28C07C303/30C07C309/65A61P9/12A61P9/10A61P9/00A61P9/06A61P11/00A61P11/06A61P25/28A61P13/12A61P19/02A61P3/10A61P35/00A61P37/08A61P37/02A61P17/00A61P27/12A61P27/06A61P27/00A61P1/00A61P17/06A61P1/16A61P13/08A61P3/04A61P25/08A61P25/06A61P25/14A61P1/02
CPCC07C225/22C07C233/33C07C309/65C07C309/66C07C321/14C07D339/04
Inventor 蒋杰李沙藕洋高瑞涛张志坚王高芳祁健斌
Owner JINAN UNIVERSITY
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