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Thiochromone compound, synthetic method and application thereof in preparing antifungal medicaments

A compound, thiochromone technology, applied in the field of F, can solve the problems of increasing antibacterial activity, unable to meet broad-spectrum antifungal activity, etc.

Inactive Publication Date: 2009-09-02
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0034] The above chemical modification methods mainly focus on the 1, 3, and 4 positions of thiochromone. The modified compounds can only increase the antibacterial activity against specific fungi, and cannot meet the requirements of broad-spectrum antifungal activity.

Method used

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  • Thiochromone compound, synthetic method and application thereof in preparing antifungal medicaments
  • Thiochromone compound, synthetic method and application thereof in preparing antifungal medicaments
  • Thiochromone compound, synthetic method and application thereof in preparing antifungal medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Synthesis of 1-(2,4-difluorophenyl)-2-(1H-imidazol-1-yl)-ethanone

[0092] The chemical structural formula is:

[0093]

[0094] Add imidazole (8.84g, 0.13mol), TEBA (1g), potassium carbonate (20.7g, 0.15) into a 250mL three-necked flask equipped with an electric stirrer, and then add dichloromethane (50mL) to make it suspend, and Stir for 30min. Put it in an ice bath, slowly add a solution of α-chloro-2,4-difluoroacetophenone (19.1 g, 0.01 mol) dissolved in 20 mL of DMF dropwise, and react at room temperature for 6 h after the dropping. After the reaction was completed, the solvent was recovered under reduced pressure, the residue was poured into 300 mL of ice water, the pH was adjusted to 5.0 with 1 mol / L hydrochloric acid under stirring, the layers were statically separated, and the aqueous layer was neutralized to pH = 7 with saturated sodium bicarbonate solution to obtain Pale yellow solid. The crude product was recrystallized from acetone to obtain 18.4 g of...

Embodiment 2

[0099] Synthesis of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

[0100] The chemical structural formula is:

[0101]

[0102] Add 1H-1,2,4-triazole (9.0g, 0.13mol), TEBA (1g, ), potassium carbonate (20.7g, 0.15mol) into a 250mL three-necked flask equipped with an electric stirrer, and then add dichloromethane (50 mL), make it suspended, and stir at room temperature for 30 min. Move it into an ice bath, slowly add a solution of α-chloro-2,4-difluoroacetophenone (19.1 g, 0.01 mol) dissolved in 20 mL of DMF dropwise, and react at room temperature for 6 h after the drop is complete. After the reaction was completed, the solvent was recovered under reduced pressure, the residue was poured into 200 mL of ice water, the pH was adjusted to 5.5 with 1 mol / L hydrochloric acid under stirring, the layers were statically separated, and the aqueous layer was neutralized to pH = 7.5 with saturated sodium bicarbonate solution to obtain Pale yellow solid. The crude product ...

Embodiment 3

[0107] Synthesis of 1-(2-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone

[0108] The chemical structural formula is:

[0109]

[0110] Add 1H-1,2,4-triazole (9.0g, 0.13mol), TEBA (1g, ), potassium carbonate (20.7g, 0.15mol) into a 250mL three-necked flask equipped with an electric stirrer, and then add dichloromethane (50 mL), make it suspended, and stir at room temperature for 30 min. Move it into an ice bath, slowly add a solution of α-chloro-2-fluoroacetophenone (17.3 g, 0.1 mol) dissolved in 20 mL of DMF dropwise, and react at room temperature for 6 h after the drop is complete. After the reaction was completed, the solvent was recovered under reduced pressure, the residue was poured into 200 mL of ice water, the pH was adjusted to 5.5 with 1 mol / L hydrochloric acid under stirring, the layers were statically separated, and the aqueous layer was neutralized to pH = 7.5 with saturated sodium bicarbonate solution to obtain Pale yellow solid. The crude product was recr...

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Abstract

The invention relates to a thiochromone compound, which has the structure as right: wherein R1 is five-membered nitrogen-containing aromatic heterocycle substituted by hydrogen, methyl, nitryl or cyano; R2 is aliphatic alkyl of C1 to C12 or unsubstituted five-membered or six-membered aromatic ring aliphatic alkyl or five-membered or six-membered aromatic ring aliphatic alkyl selectively substituted by amino group, methyl, trifluoromethyl, trifluoromethoxy, nitryl, halogen and cyano; R3 is alkyl, hydrogen, fluorine, chlorine, bromine or iodine of C1 to C4; R4 is hydrogen, fluorine, chlorine, bromine, iodine or five-membered or six-membered heterocycle containing nitrogen; and R5 and R6 are hydrogen, fluorine, chlorine, bromine, iodine, alkyl of C1 to C4, hydroxyl, oxyl of C1 to C4, cyano, nitryl, amino group or amino group substituted by alkyl of C1 to C4. The compound has application in preparing antifungal medicaments, strong bacteriostatic activity for common pathogenic fungus and deep fungal infection, low toxicity, good stability and broad antifungal spectrum.

Description

Background technique [0001] In the past two decades, with the application of a large number of broad-spectrum antibiotics, the development of bone marrow organ transplantation, the application of glucocorticoids and immunosuppressants, catheter interventional therapy, especially the prevalence of AIDS, candidemia and systemic aspergillosis, etc. Systemic fungal infections gradually increased. In particular, the incidence of invasive fungal infections is increasing, causing serious harm to human health. The most common pathogens causing invasive fungal infections include Candida species (70%-90% of invasive fungal infection cases) and Aspergillus (10%-20%). Among immunocompromised AIDS patients, the incidence of life-threatening systemic fungal infections is increasing rapidly. [0002] According to their structure and mechanism of action, antifungal drugs can be divided into five categories: polyene antifungal drugs, echinocandin antifungal drugs, pyrimidine antifungal drugs...

Claims

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Application Information

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IPC IPC(8): C07D409/04A61K31/4196A61K31/4178A61K31/454A61K31/496A61P31/10
Inventor 肖涛王锦堂李阳王振中肖伟朱红军关建宁李永建林园
Owner NANJING UNIV OF TECH
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