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A kind of 3-azacyclic thiochromone compound and its synthesis method and application in antifungal drugs

A synthesis method and compound technology, applied in antifungal agents, botanical equipment and methods, medical preparations containing active ingredients, etc., can solve the problems of narrow antibacterial spectrum and increased difficulty in the treatment of fungal infections

Active Publication Date: 2020-07-10
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, problems such as drug resistance and narrow antibacterial spectrum in clinical treatment also increase the difficulty of treatment of fungal infection diseases

Method used

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  • A kind of 3-azacyclic thiochromone compound and its synthesis method and application in antifungal drugs
  • A kind of 3-azacyclic thiochromone compound and its synthesis method and application in antifungal drugs
  • A kind of 3-azacyclic thiochromone compound and its synthesis method and application in antifungal drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1, the synthetic preparation reaction formula of formula (I) 3-oxazole thiochromone is as follows:

[0035]

[0036] The preparation steps are as follows:

[0037] Add 1-(2,4-difluorophenyl)-2-(1,2,4-triazol-1-yl)ethanone 18.4mmol, DMSO 30mL, NaOAc 43mmol, MnO 2 92mmol, stirred at 20°C, added CS dropwise at this temperature 2 22.8 mmol in 5 mL DMSO. After dropping, the temperature was controlled at 20°C and the reaction was stirred. After the reaction was completed, the reaction was filtered with suction, and the filtrate was extracted with ethyl acetate (50 mL×3) and water (50 mL). The organic phases were combined and evaporated under reduced pressure to obtain an off-white solid, which was recrystallized from anhydrous methanol to obtain the product of formula (I1) 3-(1,2,4-triazol-1-yl)-7fluorothiochromone--16.2 mmol, yield 88%.

[0038] 1 H NMR (300MHz, DMSO) δ9.16(s, 1H), 9.00(s, 1H), 8.62-8.44(m, 1H), 8.23(s, 1H), 8.03(d, J=8.9Hz, 1H) , 7.56...

Embodiment 2

[0039] Embodiment 2, the synthetic preparation reaction formula of formula (I) 3-oxazole thiochromone is as follows

[0040]

[0041] The preparation steps are as follows:

[0042] Add 1-(2,4-dichloro-5-fluorophenyl)-2-(imidazol-1-yl)ethanone 18.4mmol, DMSO 30mL, KOH 43mmol into a single-necked flask, stir at 40°C, drop Add CS 2 22.8 mmol in 5 mL DMSO. After the dropwise addition, the temperature was controlled at 40°C and the reaction was stirred for 3 h, and 100 mmol H 2 o 2 , continue to keep warm for 10h. After the reaction was completed, the reaction solution was extracted with ethyl acetate (50 mL×3) and water (50 mL). The organic phases were combined and rotary evaporated under reduced pressure to obtain an off-white solid, which was recrystallized from anhydrous methanol to obtain the product of formula (I2) 3-(imidazol-1-yl)-6-fluoro-7-chlorothiochromone--17.1mmol. The rate is 93%.

[0043] 1H NMR (300MHz, DMSO) δ8.77(s, 1H), 8.51(d, J=6.7Hz, 1H), 8.25(d, ...

Embodiment 3～ Embodiment 9

[0044] Embodiment 3~Example 9: Preparation of formula (I) 3-oxazole thiochromones

[0045] With (III) compound as raw material, prepare product formula (I) compound (target product is each compound of formula (I3)~(I9) in table 1), preparation step is the same as embodiment 1, and reaction formula is as follows

[0046]

[0047] In Examples 3 to 9, the selection of each group of the product formula (I) 3-azole thiochromones, the preparation reagents and the detection data are listed in Table 1.

[0048] Table 1

[0049]

[0050]

[0051]

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Abstract

The invention relates to a 3-azacyclo thiochromone compound. The 3-azacyclo thiochromone compound has a structure shown in the right side, wherein R3 is a hydrogen, methyl, nitro or cyano-substituted quinary azaaromatic ring; R4, R5, and R7 are respectively and independently selected from hydrogen, fluorine, chloride, bromide or iodine; R6 is selected from hydrogen, fluorine, chloride, bromide, iodine, C1-C6 oxyl, C1-C6 hydroamino groups, phenoxyl groups, and phenoxyl groups substituted by one or more of C1-C6 hydrocarbyl groups or C1-C6 hydroxy groups. The compound has the advantages that the compound can be used for preparing anti-fungi medicines, the stronger bacteria inhibiting activity on common pathogenic fungi or deep fungi infection is realized, the toxicity is low, the stability is good, and the anti-fungi spectrum is broad.

Description

technical field [0001] The invention relates to an antifungal 3-azacyclic thiochromone compound, its synthesis method and its application in the preparation of antifungal drugs. Background technique [0002] In recent years, due to the widespread use of broad-spectrum antibiotics, immunosuppressants and various hormonal drugs, as well as radiotherapy and chemotherapy, organ transplantation and HIV infection, the function of the human immune system has declined, resulting in an increase in the probability of fungal infections in the body, resulting in Morbidity and mortality from fungal diseases are on the rise. In addition, problems such as drug resistance and narrow antibacterial spectrum in clinical treatment also increase the difficulty of treatment of fungal infection diseases. Therefore, it is an urgent scientific problem to develop new antifungal drugs with broad spectrum, high efficiency and low toxicity. [0003] Activity studies have shown that thiochromones have ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/04A61K31/4196A61K31/4178A61K31/4155A01N43/653A01N43/50A01N43/56A61P31/10A01P3/00
CPCA01N43/50A01N43/56A01N43/653C07D409/04
Inventor 肖涛胡彪陈国策
Owner NANJING TECH UNIV
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