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Tetrahydroberberine thiadione compound and its preparation method and application

A technology of tetrahydroberberine and thiadione, applied in organic chemistry, antibacterial drugs, resistance to vector-borne diseases, etc., can solve the problems of limited application, low bioavailability, low solubility, etc., and achieve inhibition of bacteria and fungi. The growth, preparation of raw materials is simple, and the synthesis route is short.

Active Publication Date: 2019-12-10
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the high rigidity of berberine, its solubility in water is low, resulting in its poor absorption, low bioavailability, many times of medication, poor tolerance and curative effect, etc., which directly limits its clinical application.

Method used

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  • Tetrahydroberberine thiadione compound and its preparation method and application
  • Tetrahydroberberine thiadione compound and its preparation method and application
  • Tetrahydroberberine thiadione compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0058] Preparation of Intermediate XI

[0059]

[0060] The intermediate XI can be obtained by N-amidation of morpholine and chloroacetyl chloride.

experiment example 2

[0062] Preparation of Intermediate XII

[0063]

[0064] Berberine was obtained by demethylation reaction at 190°C with berberine as the starting material, and 9-hydroxytetrahydroberberine was obtained by reducing berberine with sodium borohydride as the reagent for reduction reaction. Add 9-hydroxytetrahydroberberine (15g, 46mmol) and hexamethylenetetramine (7.71g, 55mmol) into a 150mL round bottom flask, use trifluoroacetic acid (100mL) as solvent, stir the reaction at 120°C, thin layer Chromatographic follow-up to the end of the reaction. Hydrolyze with dilute sulfuric acid with a mass fraction of 10%, then adjust the pH to neutral with saturated sodium bicarbonate solution, extract with ethyl acetate solution, and then concentrate, recrystallize, dry and other post-treatments to obtain compound XI (11.68g). Yield 77.9%. Wherein, 9-hydroxytetrahydroberberine takes berberine hydrochloride (berberine) as a starting material to obtain berbererythine through demethylation ...

experiment example 3

[0066] Preparation of Intermediate XIII: 1-16

[0067]

[0068]

[0069] References "G, W.W.; Gopala, L.; Bheemanaboina, R.R.Y.; Zhang, G.B.; Li, S.; Zhou, C.H. The method described in J.Med.Chem.2018,146,15-37. is prepared.

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Abstract

The invention relates to tetrahydroberberine thiadione compounds as well as a preparation method and an application thereof and belongs to the technical field of chemical synthesis. The tetrahydroberberine thiadione compounds are shown in a general formula I-X, have certain inhibition activity for growth of gram-positive bacteria, gram-negative bacteria and fungi, can be used for preparing drugs for resisting bacteria and / or fungi, have no obvious drug resistance, can be combined with norfloxacin and fluconazole to more efficiently inhibit growth of bacteria and fungi and can also be intercalated into DNA to be used as a DNA intercalating agent. Besides, the preparation materials are simple, cheap and easy to obtain, the synthesis route is short and the compounds have great significance inapplication in infection resistance.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to tetrahydroberberine thiadione compounds and their preparation methods and applications. Background technique [0002] Natural berberine is a kind of quaternary ammonium isoquinoline alkaloid with condensed ring aromatic hydrocarbon structure, and its unique fused ring aromatic hydrocarbon structure and positive and negative ion centers are easy to pass through static electricity, hydrogen bonds, π-π stacking, hydrophobic interactions, etc. This kind of non-covalent bond interacts with various enzymes, proteins and other active sites in organisms, thus exhibiting various biological activities. However, due to the high rigidity of berberine, its solubility in water is low, resulting in its poor absorption, low bioavailability, many times of medication, poor tolerance and curative effect, etc., which directly limits its clinical application. . Tetrahydroberb...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D455/03A61P31/04A61P31/10
CPCA61P31/04A61P31/10C07D455/03Y02A50/30
Inventor 周成合孙航
Owner SOUTHWEST UNIV
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