Synthesis and antifungal activities of novel trifluoroethane derivatives with coumarin, indole and thiophene

Zhou, Bingyi; Yuan, Xinxin; Fan, Liangxin; Pan, Zhizhong; Chang, Xiaodan; Jiang, Shengfei; Wu, Lulu; Wang, Caixia; Yang, Gangyi; Ji, Xiaoming; Shi, Lijun; Chen, Xu

doi:10.1016/j.jscs.2022.101572

Cited by 10 publications

(4 citation statements)

References 44 publications

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“…Initially 3-substituted 4,6-dimethoxyindoles 552 (a-b) were reacted with 1 eq. POCl Bingyi Zhou et al [115] developed a protocol for synthesis of series of coumarin-indole derivatives 562 (a1-a45). Initially 3-(trifluoroacetyl)coumarins 558 (a-h) were reacted with substituted indoles 559 (a-f) in the presence of Sc(OTf) 3 catalyst and CH 2 Cl 2 and refluxed for 60 min to synthesize tertiary trifluoroethanols having indole and coumarin moieties (560) which were further reacted with 2-methylthiophene 561 (a-b, R 3 = Me, OMe) to synthesize final compounds 562 (a1-a45).…”

Section: (A4)mentioning

confidence: 99%

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Insight into Indole‐Based Heterocyclic Scaffolds: A Medicinal Chemistry Perspective

Bendi,

Versha,

Rajni

et al. 2023

ChemistrySelect

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The importance of indole‐based heterocycle scaffolds in medicinal chemistry has increased as a result of their significant pharmacological and biological characteristics. These compounds′ importance in the discovery and creation of cutting‐edge medications to treat a variety of diseases is an instance of their worth. The current study highlights the numerous methods available to create different indole‐based heterocycle scaffolds and their favourable medical uses with the literature that has been published up to 2023.

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Section: (A4)mentioning

confidence: 99%

“…Bingyi Zhou et al [115] . developed a protocol for synthesis of series of coumarin‐indole derivatives 562 (a1–a45) .…”

Section: Chemistry Of Indole Based Heterocycle Scaffoldsmentioning

confidence: 99%

Insight into Indole‐Based Heterocyclic Scaffolds: A Medicinal Chemistry Perspective

Bendi,

Versha,

Rajni

et al. 2023

ChemistrySelect

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“…Trifluoromethylated compounds are of utmost interest due to their unique properties, including their in vitro antifungal activity [53]. However, a few previous works reported that the complicated structured trifluoro derivatives of indole displayed minimal antifungal activity against Fusaruim, with an inhibition rate of about 73% at an as high concentration as 500 mcg/mL [54]. In our work, it was compound 7c containing a 3-trifluoromethylbenzyl substituent at the one position of a 2-oxoindolin moiety that showed the best-in-experiment bactericidal activity.…”

Section: Evaluation Of Antiphytopathogenic Activity Of Water-soluble ...mentioning

confidence: 99%

Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives

Bogdanov,

Neganova,

Voloshina

et al. 2023

IJMS

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A series of new fluorinated 1-benzylisatins was synthesized in high yields via a simple one-pot procedure in order to explore the possible effect of ortho-fluoro (3a), chloro (3b), or bis-fluoro (3d) substitution on the biological activity of this pharmacophore. Furthermore, the new isatins could be converted into water-soluble isatin-3-hydrazones using their acid-catalyzed reaction with Girard’s reagent P and its dimethyl analog. The cytotoxic action of these substances is associated with the induction of apoptosis caused by mitochondrial membrane dissipation and stimulated reactive oxygen species production in tumor cells. In addition, compounds 3a and 3b exhibit platelet antiaggregation activity at the level of acetylsalicylic acid, and the whole series of fluorine-containing isatins does not adversely affect the hemostasis system as a whole. Among the new water-soluble pyridinium isatin-3-acylhydrazones, compounds 7c and 5c,e exhibit the highest antagonistic effect against phytopathogens of bacterial and fungal origin and can be considered useful leads for combating plant diseases.

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“…However, ongoing challenges in antifungal activities, including the emergence of resistant strains and limitations in current therapies, underscore the urgent need for innovative solutions. [14,16,17] The exploration of indolebased compounds not only addresses these challenges but also holds the potential to overcome existing limitations, providing a crucial step forward in the quest for more effective and versatile antifungal drugs with improved clinical outcomes. Based on recent research findings and previously collected data from sources, [18][19][20][21][22][23][24][25] we propose structures evaluated by the amalgamation of molecular fragments possessing diverse antimicrobial activity as depicted in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

Indole clubbed 2,4‐thiazolidinedione linked 1,2,3‐triazole as a potent antimalarial and antibacterial agent against drug‐resistant strain and molecular modeling studies

Upadhyay,

Mokariya,

Patel

et al. 2024

Archiv der Pharmazie

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In the face of escalating challenges of microbial resistance strains, this study describes the design and synthesis of 5‐({1‐[(1H‐1,2,3‐triazol‐4‐yl)methyl]‐1H‐indol‐3‐yl}methylene)thiazolidine‐2,4‐dione derivatives, which have demonstrated significant antimicrobial properties. Compared with the minimum inhibitory concentrations (MIC) values of ciprofloxacin on the respective strains, compounds 5a, 5d, 5g, 5l, and 5m exhibited potent antibacterial activity with MIC values ranging from 16 to 25 µM. Almost all the synthesized compounds showed lower MIC compared to standards against vancomycin‐resistant enterococcus and methicillin‐resistant Staphylococcus aureus strains. Additionally, the majority of the synthesized compounds demonstrated remarkable antifungal activity, against Candida albicans and Aspergillus niger, as compared to nystatin, griseofulvin, and fluconazole. Furthermore, the majority of compounds exhibited notable inhibitory effects against the Plasmodium falciparum strain, having IC50 values ranging from 1.31 to 2.79 μM as compared to standard quinine (2.71 μM). Cytotoxicity evaluation of compounds 5a–q on SHSY‐5Y cells at up to 100 μg/mL showed no adverse effects. Comparison with control groups highlights their noncytotoxic characteristics. Molecular docking confirmed compound binding to target active sites, with stable protein–ligand complexes displaying drug‐like molecules. Molecular dynamics simulations revealed dynamic stability and interactions. Rigorous tests and molecular modeling unveil the effectiveness of the compounds against drug‐resistant microbes, providing hope for new antimicrobial compounds with potential safety.

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Synthesis and antifungal activities of novel trifluoroethane derivatives with coumarin, indole and thiophene

Cited by 10 publications

References 44 publications

Insight into Indole‐Based Heterocyclic Scaffolds: A Medicinal Chemistry Perspective

Insight into Indole‐Based Heterocyclic Scaffolds: A Medicinal Chemistry Perspective

Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives

Indole clubbed 2,4‐thiazolidinedione linked 1,2,3‐triazole as a potent antimalarial and antibacterial agent against drug‐resistant strain and molecular modeling studies

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