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用于口腔环境的5-羟基-3-苯基-1H-吡唑-1-碳硫酰胺的合成及其抗真菌活性评估

Synthesis and evaluation of the antifungal activity of 5-hydroxy-3-phenyl-1H-pyrazole-1-carbothioamide for use in the oral environment.

作者信息

Amin Zadeh Hossein, Zomorodkia Ali Asghar, Hadi Saeid, Mohammad Zadeh Iman, Sabetghadam Seyed Abd Alreza, Hadi Vahid

机构信息

Department of Chemistry, Shahid Bahonar University of Kerman, 76169, Iran.

Department of Chemical Engineering, South Tehran Branch, Islamic Azad University, Tehran, Iran.

出版信息

J Oral Biol Craniofac Res. 2024 Mar-Apr;14(2):211-215. doi: 10.1016/j.jobcr.2024.01.008. Epub 2024 Mar 1.

Abstract

BACKGROUND AND AIM

Candida albicans and Candida tropicalis, can cause superficial infections of the oral mucosa as well as disseminated bloodstream and deep-tissue infections. The most frequently employed class of antifungals used for Candida infection treatment are the azole antifungals. Their low price, low toxic qualities, and availability for oral use make fluconazole and similar azole antifungals the preferred treatment for various infections caused by Candida. Nevertheless, developed and intrinsic resistance to antifungals of the azole family has been widely documented in association with various species of Candida. Candida infection management requires synthesizing new compounds to improve azole class antifungals, as Candida isolates resistant to azole are increasingly encountered in the clinical setting. This study aimed to synthesize a new azole compound and investigate its antifungal activity.

METHODS

In this experimental study, 5-hydroxy-3-phenyl-1H-pyrazole-1-carbothioamide was synthesized by the reaction between thiosemecarbazide and ethylbezoylacetate. The structure of the synthesized compound was characterized by different techniques such as Fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR) spectra and its antifungal activity against Candida albicans and Candida tropicalis was investigated by the Spread Plat method to determine its minimum fungicidal concentration (MFC) and minimum inhibitory concentration (MIC).

RESULTS AND DISCUSSION

The Spread Plat test demonstrated that with the increase in 5-hydroxy-3-phenyl-1H-pyrazole-1-carbothioamide concentration, colonies of fungi were increasingly eliminated at a significant level(p < 0.001). At a concentration of 1000 ppm, all Candida albicans and Candida tropicalis colonies were destroyed.

CONCLUSIONS

The results indicate that the synthesized compound showed a promising antifungal effect. On the other hand, it had a suitable spectrum of effect, because it showed antifungal effects on both Candida albicans and Candida tropicalis strains.

摘要

背景与目的

白色念珠菌和热带念珠菌可引起口腔黏膜的浅表感染以及播散性血流感染和深部组织感染。用于念珠菌感染治疗的最常用抗真菌药物类别是唑类抗真菌药。氟康唑和类似的唑类抗真菌药价格低廉、毒性低且可供口服,使其成为治疗由念珠菌引起的各种感染的首选药物。然而,唑类家族抗真菌药的获得性耐药和固有耐药已在多种念珠菌中广泛报道。由于在临床环境中越来越多地遇到对唑类耐药的念珠菌分离株,念珠菌感染的管理需要合成新的化合物以改进唑类抗真菌药。本研究旨在合成一种新的唑类化合物并研究其抗真菌活性。

方法

在本实验研究中,通过硫代氨基脲与乙基苯甲酰乙酸酯反应合成了5-羟基-3-苯基-1H-吡唑-1-碳硫酰胺。通过傅里叶变换红外光谱(FT-IR)和核磁共振(NMR)光谱等不同技术对合成化合物的结构进行了表征,并通过涂布平板法研究了其对白色念珠菌和热带念珠菌的抗真菌活性,以确定其最低杀菌浓度(MFC)和最低抑菌浓度(MIC)。

结果与讨论

涂布平板试验表明,随着5-羟基-3-苯基-1H-吡唑-1-碳硫酰胺浓度的增加,真菌菌落被显著消除的程度越来越高(p < 0.001)。在1000 ppm的浓度下,所有白色念珠菌和热带念珠菌菌落均被破坏。

结论

结果表明合成的化合物显示出有前景的抗真菌作用。另一方面,它具有合适的效应谱,因为它对白色念珠菌和热带念珠菌菌株均显示出抗真菌作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5294/10912861/8745dedac890/ga1.jpg

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