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A kind of thiochromanone derivative and its preparation method and application

A technology of thiochromanone and its derivatives, which is applied in the field of thiochromanone derivatives and their preparation, can solve the problems of no discovery and achieve the effects of high specificity, expanding drug selection, and alleviating drug resistance

Active Publication Date: 2019-02-22
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the industry has not found research reports on related pharmaceutical preparations that specifically act on the target of N-myristoyltransferase in pathogenic fungi

Method used

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  • A kind of thiochromanone derivative and its preparation method and application
  • A kind of thiochromanone derivative and its preparation method and application
  • A kind of thiochromanone derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] (1) Dissolve 0.2mol of p-hydroxythiophenol and 0.24mol of β-chloropropionic acid in 30mL of alkaline aqueous solution (KOH aqueous solution with a pH value of 12), react at 80°C for 2.5h, follow the reaction until complete by TLC, Cool to room temperature, adjust the pH value of the reaction solution to 2 with concentrated hydrochloric acid (mass ratio concentration is 36%), separate out a large amount of white precipitates, let stand overnight, filter with suction, wash the filter cake with water, wash with 50mL ethanol aqueous solution (V 乙醇 :V 水 =1:1) recrystallization, vacuum drying overnight at 40°C to obtain 3-p-hydroxyphenyl-3-thiopropionic acid; the chemical reaction process is as follows:

[0044]

[0045] (2) Dissolve 10 g of 3-p-hydroxyphenyl-3-thiopropionic acid in 40 mL of concentrated sulfuric acid (mass ratio concentration is 98%), place it at room temperature for ice thawing, a large amount of solids are precipitated, and use 20 mL of ethanol after su...

Embodiment 2

[0062] Step (1)-(4) is the same as embodiment 1, Where m is 2, step (5) is: oxidizing 1mmol of 3-benzyl-6-(3-bromopropoxy)thiochroman-4-one, 1.2mmol of benzylamine, and 1.5mmol of hydrogen Potassium was dissolved in 8 mL of 1,4-dioxane solvent, reacted at 90°C for 12h, TLC followed the reaction, and stopped the reaction when the product point no longer changed; after the reactant was cooled to room temperature, the solvent was distilled off under reduced pressure, and the obtained Silica gel column for solid (V 乙酸乙酯 :V 丙酮 =4: 1) purification, promptly obtains compound 26 in table 1; Its productive rate is 50%, finds that when the reaction condition of the (5) step of embodiment 1 is 90 ℃ of reaction 9-12 hours in the course of research , Compound 26, which was originally a by-product, became the main product.

[0063] The chemical reaction formula of (5) step is:

[0064]

[0065] The compounds prepared by the methods of Example 1 and Example 2 and their physical and c...

Embodiment 3

[0076] Embodiment 3 The antifungal activity detection test of the compound prepared by the present invention

[0077] In order to explore the in vitro antifungal activity of the synthesized compounds, this experiment respectively measured Candida albicans (Canidia albicans, C.a), Cryptococcus neoformans (Cryptococcus neoformans, C.n), Aspergillus niger (Aspergillus niger, A.n) Mucorus racemosa ( Mucor racemosus, M.r), gypsum-like Microsporum (Microsporum gypseum, M.g) and flocculent Epidermophyton (Epidermophyton floccosum, E.f) and other six kinds of fungi antibacterial activity. The tested fungi were all from the Culture Collection Center of the Chinese Academy of Medical Sciences.

[0078] This experiment adopts the microdilution method to carry out antifungal activity test to 6 kinds of tested fungi, 8 mg of 46 target compounds prepared in Example 1 are first dissolved with 625 μL of dimethyl sulfoxide (DMSO), and 50 μL of this solution is incubated with 2.5 mL of 1640 so...

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Abstract

The invention discloses a thiochromanone derivative and meanwhile discloses a thiochromanone derivative and a preparation method and application thereof. Experimental results show that the compound has the advantages of being wide in antibacterial spectrum, high in selectivity and free of drug resistance, the antibacterial activity level of the derivative is higher, the thiochromanone contained in the derivative has high lipid solubility, the problem that at present, the cytomembrane penetrating power of an NMT inhibitor is insufficient can be improved, and the thiochromanone derivative is used for preparing antibacterial pharmaceutic preparations for treating fungal diseases caused by pathogenic bacteria such as candida albicans, cryptococcus neoformans, aspergillus niger, mucor, microsporum gypseum and epidermophyton floccosum and has huge potential economic benefit and social value.

Description

technical field [0001] The invention relates to antifungal drugs and a preparation method thereof, in particular to a thiochromanone derivative, a preparation method and application thereof. Background technique [0002] Fungi are eukaryotic organisms that have similar structures and physiological metabolic processes to host cells. According to the different sites of infection caused by fungi, it can be divided into superficial fungal infection and deep fungal infection. Superficial fungal infections are mainly caused by various tinea fungi, such as tinea pedis, tinea capitis, tinea corporis, etc. Currently, griseofulvin, nystatin, and ketoconazole are mainly used as therapeutic drugs. Deep fungal infection is harmful and even life-threatening. The main pathogenic fungi include Candida albicans, Cryptococcus neoformans, Aspergillus, and Mucormyces. Under normal circumstances, these fungi do not cause diseases in the body, but they may cause diseases under the condition of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D335/06C07D409/12C07D409/06C07D409/14A61K31/382A61K31/5377A61K31/4709A61P31/10
CPCC07D335/06C07D409/06C07D409/12C07D409/14
Inventor 宋亚丽乔晓强钟一凡韩晓燕李生彬齐慧
Owner HEBEI UNIVERSITY
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