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Novel 2,3,3a,4-tetrahydro thiochromeno [4,3-c] pyrazole antiinflammatory antimycotic compound

An antifungal and compound technology, applied in antifungal agents, anti-inflammatory agents, organic chemistry, etc., can solve the problems of limited application, high toxicity and side effects, etc., achieve a wide range of biological activities, simple synthesis method, good research value and application foreground effect

Inactive Publication Date: 2009-01-28
杨更亮
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Amphotericin B and triazole fluconazole drugs are also limited in application due to their severe side effects

Method used

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  • Novel 2,3,3a,4-tetrahydro thiochromeno [4,3-c] pyrazole antiinflammatory antimycotic compound
  • Novel 2,3,3a,4-tetrahydro thiochromeno [4,3-c] pyrazole antiinflammatory antimycotic compound
  • Novel 2,3,3a,4-tetrahydro thiochromeno [4,3-c] pyrazole antiinflammatory antimycotic compound

Examples

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Effect test

preparation example 1

[0032] The preparation of compound 1 thiophenol in Attached Table 2: Take 0.2mol benzenesulfonyl chloride and place it in a three-neck flask, add 27g metallic zinc powder, stir evenly, add 4M H 2 SO 4 , Stir while adding dropwise, after reacting for 6-8 hours, separate by filtration, wash, dry, and purify by recrystallization. The yield is 89.8-92.1%, and the melting point is 70.7°C. If substituted thiophenols are synthesized, substituted benzenesulfonyl chlorides can be used to synthesize them, and the method is basically the same as the above steps; for example, the yield of halobenzenesulfonyl chlorides is generally between 77% and 89%.

preparation example 2

[0034] Preparation of Compound 2 [6-Fluoro-Sekelmanone] in Attached Table 2: Dissolve 50 mmol of the above-prepared fluorothiophenol in 2M NaOH solution (an appropriate amount of ethanol may be added). Dissolve 8.2g of β-chloropropionic acid (or 10g of its methyl ester) in the calculated amount of Na 2 CO 3 solution, and then mixed with the above solution, ultrasonication, reflux for 6-8 hours, suction filtration after removing the alcohol, and the filtrate with 4M H 2 SO 4 .Acidify and stir for 1-2 hours, filter with suction, wash and dry with water to obtain β-(substituted phenylthio)-propionic acid, then condense with polyphosphoric acid (or concentrated sulfuric acid) for 24 hours, separate and purify to obtain 6-fluoro-Sekelman ketone. Yield 70-75%, melting point 92-93°C. The measured physical and chemical constants are shown in Table 2.

preparation example 3

[0036] Attached Table 2 compound 3 [3-benzyl-6-fluoro-thiochromanone] in 38mmol 10% KOH solution and 7.4ml absolute ethanol, add 30mmol 6-fluoro-thiochromanone (3) under stirring , the temperature was controlled at 22-30°C, 30mmol benzaldehyde was added, and the reaction temperature was maintained for 3.5h. The reaction solution was placed in the refrigerator for 10 h, cooled to 0°C, filtered and washed with water until neutral. Recrystallize and dry with ethanol / water to give light yellow 3-benzyl-6-fluoro-thiochromanone with a yield of 85-92%. The measured physical and chemical constants are shown in Table 2.

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Abstract

The invention discloses a novel nitrogen and sulfur-contained benzotricycloheterocycle compound having anti-inflammation and antifungal activities, namely 2, 3, 3a, 4-tetrahydrothiochromeno pyrazole compound. In the invention, aiming at the existing research and development condition of few antifungal drug and high toxicity in the prior art, the novel 2, 3, 3a, 4-tetrahydrothiochromeno pyrazole compound is designed and synthesized, fungi experiments are carried out and results from the experiments indicate that the compound has favorable antifungal activity. The novel benzotricycloheterocycle compound of the invention has the advantages of simple synthesis method and easily obtained raw materials, and the specifications show the synthesis method in detail. The products of the invention can be used for anti-inflammation and antifungal drugs.

Description

technical field [0001] The patent of the present invention relates to heterocyclic compounds containing nitrogen and sulfur, in particular to a class of 2,3,3a,4-tetrahydrothiochromenopyrazole series anti-inflammatory and anti-fungal synthetic drugs. Background technique [0002] Fungi are eukaryotic organisms that have a similar structure and physiological metabolic process to host cells. According to the different infection sites caused by fungi, they can be divided into superficial fungal infections and deep fungal infections. Superficial fungal infections are mainly caused by various tinea fungi, such as tinea pedis, tinea capitis, tinea corporis, etc. Currently, greymycin, nystatin, and ketoconazole are often used as therapeutic drugs. Deep fungal infection is harmful and even life-threatening. It is mainly caused by pathogenic fungi, including Candida albicans, Cryptococcus neoformans, Aspergillus, Mucor, etc. These fungi are members of the normal flora in the body and...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61K31/4162A61P29/00A61P31/10
CPCC07D495/04A61P29/00A61P31/10
Inventor 杨更亮马正月祝士国
Owner 杨更亮
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