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Antifungal agent-sulfur chromanone thiosemicarbazone compounds

A kind of technology of thiosemicarbazone and thiochromanone, applied in the field of medicine

Active Publication Date: 2009-05-20
SHENYANG PHARMA UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The thiochromanone amino(thio)urea derivatives have no relevant reports at present

Method used

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  • Antifungal agent-sulfur chromanone thiosemicarbazone compounds
  • Antifungal agent-sulfur chromanone thiosemicarbazone compounds
  • Antifungal agent-sulfur chromanone thiosemicarbazone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] 1-(6,8-dichloro-4-thiochromanone) semicarbazone

[0082] 23.3g (0.1mol) of 6,8-dichloro-4-thiochromanone, 75g (0.1mol) of semicarbazide, and 40.5g (0.05mol) of sodium acetate were dissolved in 100ml of ethanol, and the pH of the reaction solution was adjusted with hydrochloric acid= 3. Heat to reflux for 2 hours, cool to room temperature, precipitate solid, filter with suction, rinse with a small amount of ethanol, and dry to obtain a crude product. The product obtained by recrystallization with n-butanol as a solvent is a white solid, the yield is 24g, the yield is 83%, mp: 197~199°C, LC-MS (m / z): 290[M+H] + , 1 H-NMR (DMSO): 2.85-2.89(t, 2H), 3.05-3.09(t, 2H), 6.68(s, 2H), 7.56(s, 1H), 8.37(s, 1H), 9.50(s, 1H)

Embodiment 2

[0084] 1-(6,8-Dichloro-4-thiochromanone)thiosemicarbazone

[0085] Dissolve 23.3g (0.1mol) of 6,8-dichloro-4-thiochromanone and 91g (0.1mol) of thiosemicarbazide in 100ml of ethanol, add dropwise 0.5ml of glacial acetic acid, heat to reflux for 5 hours, and cool After reaching room temperature, a solid precipitated out, was suction filtered, rinsed with a small amount of ethanol, and dried to obtain a crude product. The product obtained by recrystallization with n-butanol as a solvent is a white solid, the yield is 27.8g, the yield is 91%, mp: 174~176°C, LC-MS (m / z): 307[M+H] + , 1 H-NMR (DMSO): 2.92-2.94 (t, 2H), 2.97-2.99 (t, 2H), 7.52-7.53 (d, 1H), 8.28 (s, 1H), 8.36 (s, 1H), 8.43- 8.44(d, 1H), 10.25(s, 1H)

Embodiment 3

[0087] 1-[6,8-Dichloro-3-(N,N-dimethylamino)methyl-4-thiochromanone]semicarbazone hydrochloride

[0088] Method A:

[0089] 32.7g (0.1mol) of 6,8-dichloro-3-(N,N-dimethylamino)methyl-4-thiochromanone hydrochloride, 75g (0.1mol) of semicarbazide, 40.5g of sodium acetate (0.05mol) was dissolved in 100ml of ethanol, the pH of the reaction solution was adjusted to 3 with hydrochloric acid, heated to reflux for 6 hours, cooled to room temperature, a solid precipitated, filtered with suction, rinsed with a small amount of ethanol, and dried to obtain a crude product. The product obtained by recrystallization with n-butanol as a solvent is a white solid, the yield is 28.7g, the yield is 75%, mp: 207~209°C, LC-MS (m / z): 383[M+H] + , 1 H-NMR (DMSO): 2.22-2.27 (m, 6H), 2.50 (s, 2H), 2.61-2.65 (t, 2H), 2.75-2.80 (t, 2H), 6.78 (s, 2H), 7.59 ( s, 1H), 8.49(s, 1H), 10.10(s, 1H)

[0090] Method B:

[0091]29.1 g (0.1 mol) of 1-(6,8-dichloro-4-thiochromanone) semicarbazone prepared by me...

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PUM

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Abstract

The invention pertains to the technical field of medicaments, more particularly relates to a (sulfur) urea derivative with substituted semicarbazone thiochromanones and provides a novel and efficient antifungal agent. The structural formula of the derivative is shown as the Formula I. The invention also relates to a chemically acceptable compound of the derivative and a medicament combination taking the compound as an active ingredient. As a novel antifungal agent, the compound has relatively strong effect of killing pathomycete commonly seen clinically and is expected to overcome the defects that azoles antifungal medicaments widely used in clinical treatment has serious toxic side effect and is easy to generate medicament resistance, and the like. The compound is prepared by the condensation of substitutable thiochromanones and substitutable semicarbazone (sulfur) in an organic solvent.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to thiochromanone semisemicarbazide (thio) urea series with antifungal activity and pharmaceutically acceptable salts thereof. Background technique [0002] Mycosis is a multiple, refractory disease. In recent years, due to the extensive use of drugs such as antibiotics, hormones, and immunosuppressants; the widespread use of large-scale operations such as catheters, intubations, and organ transplants, fungal infections, especially deep fungal infections, have become increasingly serious. Drugs for the treatment of fungal diseases are scarce. Azole antifungal drugs are still the first choice. Although these antifungal drugs have certain curative effects, their clinical application is limited due to their obvious toxic and side effects and poor curative effect on deep fungal infections. Therefore, it is still a very meaningful work to develop antifungal drugs with high efficiency,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/06A61K31/382A61P31/10
Inventor 郭春方林刘扬苏昕李翠丽孙历骆伟梁隆黄耀宗
Owner SHENYANG PHARMA UNIVERSITY
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