Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents

Zhao, Shizhen; Zhang, Xiangqian; Peng, Wei; X, Su; Zhao, Liyu; Wu, Mengya; Hao, Chenzhou; Liu, Chunchi; Cheng, Maosheng

doi:10.1016/j.ejmech.2017.05.043

Cited by 43 publications

(23 citation statements)

References 25 publications

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“…The resulted disruption of fungal cell membrane morphology and functional integrity, with the subsequent loss of intracellular constituents and cell lysis, is responsible for their fungistatic effect [7]. However, drawbacks, such as narrow antifungal spectrum, low bioavailability, systemic toxicity, and increasing drug tolerance, require the development of novel molecules with improved pharmacokinetics and therapeutic efficiency [10].…”

Section: Of 17mentioning

confidence: 99%

Novel 2,4-Disubstituted-1,3-Thiazole Derivatives: Synthesis, Anti-Candida Activity Evaluation and Interaction with Bovine Serum Albumine

et al. 2020

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Herein we report the synthesis of two novel series of 1,3-thiazole derivatives having a lipophilic C4-substituent on account of the increasing need for novel and versatile antifungal drugs for the treatment of resistant Candida sp.-based infections. Following their structural characterization, the anti-Candida activity was evaluated in vitro while using the broth microdilution method. Three compounds exhibited lower Minimum Inhibitory Concentration (MIC) values when compared to fluconazole, being used as the reference antifungal drug. An in silico molecular docking study was subsequently carried out in order to gain more insight into the antifungal mechanism of action, while using lanosterol-C14α-demethylase as the target enzyme. Fluorescence microscopy was employed to further investigate the cellular target of the most promising molecule, with the obtained results confirming its damaging effect towards the fungal cell membrane integrity. Finally, the distribution and the pharmacological potential in vivo of the novel thiazole derivatives was investigated through the study of their binding interaction with bovine serum albumin, while using fluorescence spectroscopy.

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Section: Of 17mentioning

confidence: 99%

Novel 2,4-Disubstituted-1,3-Thiazole Derivatives: Synthesis, Anti-Candida Activity Evaluation and Interaction with Bovine Serum Albumine

et al. 2020

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“…are still the three main pathogens of fungal infections. Over the last few decades, the occurrence of systemic fungal infections has increased considerably in immunocompromised hosts, particularly patients who receive cancer chemotherapy or patients with AIDS and undergone organ transplantation [1][2][3]. Some research teams stated that Candida albicans (C. albicans) which caused severe mucosal infections with potentially fatal invasive infections was the most common fungus in these patients [4,5].…”

Section: Introductionmentioning

confidence: 99%

Antifungal Activity of Some Benzimidazole-Hydrazones

Osmaniye

Çevik

2019

Cumhuriyet Science Journal

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In the present work, 15 4-(1-(prop-2-in-1-yl)-1H-benzoimidazole-2-yl)-N'-(substitutedmethylene)benzohydrazide derivatives (4a-4o) were re-synthesized to evaluate their antifungal activity. Structure identification of synthesized compounds was elucidated by 1 H-NMR, 13 C-NMR, and HRMS spectroscopic methods. Inhibitory potential of the re-synthesized compounds was investigated against Candida supp. The compounds 4e and 4l showed significant anti fungal activity. Consistent with the activity studies, 4e was found to be potent derivative with its MIC50 value of (1.95 µg/mL) against Candida glabrata. And 4l was found to be potent derivative with its MIC50 value of (1.95 µg/mL) against Candida krusei.Özet. Mevcut çalışmada, 15 4-(1-(prop-2-in-1-il)-1H-benzimidazol-2-il)-N'-(sübstitüemetilen) benzohidrazit türevleri (4a-4o), antifungal aktivitelerini değerlendirmek üzere yeniden sentezlendi. Sentezlenen bileşiklerin yapı tanımlamaları 1 H-NMR, 13 C-NMR ve HRMS spektroskopik yöntemlerle açıklandı. Yeniden sentezlenen bileşiklerin antifungal etkinlikleri Candida türlerine karşı değerlendirildi. Bileşik 4e ve 4l önemli aktivite gösterdi. Aktivite çalışmaları ile uyumlu olarak, 4e bileşiği Candida glabrata'ya karşı 1.95 µg / mL MIC50 değeri ile güçlü bir türev olarak bulundu. Aynı zamanda 4l bileşiği Candida krusei'ye karşı 1.95 µg / mL MIC50 değeri ile güçlü bir türev olarak bulundu.

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Section: Introductionmentioning

confidence: 99%

“…The great number of heterocyclic compounds is used in medicine as drugs for miscellaneous diseases. The drugs that have the heterocyclic core in their frame have some specific activity such as antifungal activity, 46 anti-inflammation, 47 antibacterial, 48 antioxidants, 49 anticonvulsant, 50 antiallergic, 51 herbicidal activity, 52 and and anticancer. 49 Although a number of studies have been reported on bioactivity of ferrocene and xanthone individually, 1-6,44,53-55 based on our knowledge, there is still no report on anticancer polymers bearing ferrocene and xanthone in the main chain.…”

mentioning

confidence: 99%

Novel anticancer and antibacterial organometallic polymer based on ferrocene as a building block and xanthone bioactive scaffolds: Synthesis, characterization, and biological study

Lakouraj

Hasantabar

Tashakkorian

et al. 2018

Polymers for Advanced Techs

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Poly(azine ferrocene‐triazole‐xanthone amide) (PAFTXA) was successfully synthesized from azine ferrocene bisacetylene (AFcB) and 2,7‐(N‐2‐azidoacetamide) xanthone (NAzX) by using click chemistry protocol. In this paper, innovative AFcB moiety incorporated in this procedure as a monomer. This monomer was prepared in three steps from ferrocene scaffold, and the synthetic processes were discussed in details. Characterization of the synthesized novel intermediate materials, monomer, and the resulting polymer was performed by nuclear magnetic resonance, Fourier transform infrared, thermal gravimetric analysis, differential scanning calorimetry, and ultraviolet‐visible spectrophotometer. In addition, the in vitro antibacterial activity of the polymer was appraised against Gram‐positive and Gram‐negative bacteria by using minimum inhibitory concentration method. Moreover; antitumoral effects of synthesized polymer were evaluated on Hela, MCF‐7, and Saos cancer cell lines and compared with normal fibroblast cell line by means of 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. Promising antiproliferative effects were detected on both epitheloid and mesenchymal cancer cell lines depending on PAFTXA concentration and time. Survey on its characteristic features revealed the proficiencies of our prepared biomaterial such as its high thermal stability as well as valuable antitumoral and antibacterial capabilities that make it an appreciable candidate for further bioapplications.

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Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents

Cited by 43 publications

References 25 publications

Novel 2,4-Disubstituted-1,3-Thiazole Derivatives: Synthesis, Anti-Candida Activity Evaluation and Interaction with Bovine Serum Albumine

Novel 2,4-Disubstituted-1,3-Thiazole Derivatives: Synthesis, Anti-Candida Activity Evaluation and Interaction with Bovine Serum Albumine

Antifungal Activity of Some Benzimidazole-Hydrazones

Novel anticancer and antibacterial organometallic polymer based on ferrocene as a building block and xanthone bioactive scaffolds: Synthesis, characterization, and biological study

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