1,2,3‐Triazole derivatives of 3‐ferrocenylidene‐2‐oxindole: Synthesis, characterization, electrochemical and antimicrobial evaluation

Yagnam, Swetha; Reddy, Eda Rami; Trivedi, Rajiv; Krishna, Narra Vamshi; Giribabu, Lingamallu; Rathod, Balaji; Prakasham, R. S.; Sridhar, Balasubramanian

doi:10.1002/aoc.4817

Cited by 15 publications

(9 citation statements)

References 63 publications

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“…The antifungal activity of metal compounds has been investigated even less than their antibacterial properties. ,,− Figure presents an overview of selected metal compounds with measured antifungal activity. Gasser and coworkers recently published an expansive review of the metal-based antifungals research field .…”

Section: Introductionmentioning

confidence: 99%

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Metal Complexes as Antifungals? From a Crowd-Sourced Compound Library to the First In Vivo Experiments

Frei

Elliott

Kan

et al. 2022

JACS Au

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There are currently fewer than 10 antifungal drugs in clinical development, but new fungal strains that are resistant to most current antifungals are spreading rapidly across the world. To prevent a second resistance crisis, new classes of antifungal drugs are urgently needed. Metal complexes have proven to be promising candidates for novel antibiotics, but so far, few compounds have been explored for their potential application as antifungal agents. In this work, we report the evaluation of 1039 metal-containing compounds that were screened by the Community for Open Antimicrobial Drug Discovery (CO-ADD). We show that 20.9% of all metal compounds tested have antimicrobial activity against two representative Candida and Cryptococcus strains compared with only 1.1% of the >300,000 purely organic molecules tested through CO-ADD. We identified 90 metal compounds (8.7%) that show antifungal activity while not displaying any cytotoxicity against mammalian cell lines or hemolytic properties at similar concentrations. The structures of 21 metal complexes that display high antifungal activity (MIC ≤1.25 μM) are discussed and evaluated further against a broad panel of yeasts. Most of these have not been previously tested for antifungal activity. Eleven of these metal complexes were tested for toxicity in the Galleria mellonella moth larva model, revealing that only one compound showed signs of toxicity at the highest injected concentration. Lastly, we demonstrated that the organo-Pt(II) cyclooctadiene complex Pt1 significantly reduces fungal load in an in vivo G. mellonella infection model. These findings showcase that the structural and chemical diversity of metal-based compounds can be an invaluable tool in the development of new drugs against infectious diseases.

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Section: Introductionmentioning

confidence: 99%

“…Selected structures of metal complexes with reported antifungal activity containing iron ( 1, , 2, 3, 4 ), cobalt ( 5, 6 ), palladium ( 7 ), gold ( 8 ), manganese ( 9 ), nickel ( 10, 11 ), ruthenium ( 12 ), rhenium ( 13 ), and iridium ( 14 ).…”

Section: Introductionmentioning

confidence: 99%

Metal Complexes as Antifungals? From a Crowd-Sourced Compound Library to the First In Vivo Experiments

Frei

Elliott

Kan

et al. 2022

JACS Au

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“…32 Figure 1. Selected structures of metal complexes with reported antifungal activity containing iron (1 [34][35] , 2 35 , 3 36 , 4 37 ) , cobalt (5 28 , 6 38 ), palladium (7 39 ), gold (8 40 ), manganese (9 41 ), nickel (10 42 , 11 43 ), ruthenium (12 44 ), rhenium (13 30 ), and iridium (14 45 )…”

Section: Introductionmentioning

confidence: 99%

“…Over the last years a small number of reports have been published on several different antifungal metal complexes. 28,30,[34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51] Figure 1 presents an overview of selected metal compounds with measured antifungal activity. Gasser and coworkers recently published an expansive review of the metalbased antifungals research field.…”

Section: Introductionmentioning

confidence: 99%

Metal Complexes as Antifungals? – From a Crowd-Sourced Compound Library to First In Vivo Experiments

Frei

Elliott

Kan

et al. 2022

Preprint

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There are currently fewer than ten antifungal drugs in clinical development, but new fungal strains, which are resistant to most current antifungals are spreading rapidly across the world. To prevent a second resistance crisis, new classes of antifungal drugs are urgently needed. Metal complexes have proven to be promising candidates for novel antibiotics, but so far, few compounds have been explored for their potential application as antifungal agents. In this work we report the evaluation of 1039 metal-containing compounds that were screened by the Community for Open Antimicrobial Drug Discovery (CO-ADD). We show that 20.9% of all metal compounds tested have antimicrobial activity against two representative Candida and Cryptococcus strains, compared with only 1.1% of the >300,000 purely organic molecules tested through CO-ADD. We identified 90 metal compounds (8.7%) that show antifungal activity while not displaying any cytotoxicity against mammalian cell lines or haemolytic properties at similar concentrations. The structures of 21 metal complexes which display high antifungal activity (MIC ≤ 1.25 µM) are discussed and evaluated further against a broad panel of yeasts. Most of these have not been evaluated for antifungal activity. Eleven of these metal complexes were tested for toxicity in the Galleria mellonella moth larvae model, revealing that only one compound showed signs of toxicity at the highest injected concentration. Lastly, we demonstrated that the organo-Pt(II) cyclooctadiene complex Pt1 significantly reduces fungal load in an in vivo G. mellonella infection model. These findings showcase that the structural and chemical diversity of metal-based compounds can be an invaluable tool in the development of new drugs against infectious diseases.

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“…The former method for the synthesis of 1,2,3-triazole rings was the thermal condition at high temperatures in general through the coupling reaction between alkynes and organic azides to obtain a mixture of 1,4-and 1,5-disubstituted-1,2,3-triazoles [4]. Moreover, during recent decades CuAAC has developed as a unique alternative and received much consideration due to its exclusive regioselectivity, extensive substrate scope, mild and green reaction conditions, and simple purification which have made it the method of choice for making the most stable connections by means of 1,4-disubstituted-1,2,3-triazoles since its discovery [5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles

2021

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The synthesis and catalytic activity of three 1,2,3-triazole-based ionic organicinorganic hybrids as novel water-soluble catalysts for the efficient preparation of spirooxindole derivatives are described. At first, three different 1,2,3-triazoles were prepared by click reaction. Then, these synthesized compounds were reacted with 1,4-butane sultone to generate novel solid 1,2,3-triazolium-N-butyl sulfonate zwitterions. In the next step, the newly synthesized organic zwitterions were treated with an aqueous solution of phosphotungstic acid to give three novel 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstates as targeted organic-inorganic hybrid catalysts. The prepared catalysts were fully characterized using FTIR, 1 H and 13 C NMR, XRD, elemental analysis (CHNS), ESI-MS, DSC, and TG techniques. The introduced novel SO 3 H-functionalized ionic hybrid catalysts have a cationic organic triazolium with phosphotungstate anion and are water-soluble with appropriate thermal stability. Their catalytic activity was explored for the synthesis of spirooxindoles via the three-component reaction of 1,3-dicarbonyl compounds, barbituric acid, and isatin derivatives. The synthesis of desired spirooxindole products was performed in acceptable times with excellent yields in the presence of low loading amount of the prepared 1,2,3-triazolium-N-butyl sulfonic acid phosphotungstate catalysts (10 mmol%) in water. Some highlighted superiorities of the introduced organic-inorganic hybrids in comparison with most of the previously reported catalysts are as follows: clean and straightforward preparation, novelty of the catalysts, green conditions, ease of recovery, and reusability up to three repeated runs with no significant decrease in the catalytic stability.

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1,2,3‐Triazole derivatives of 3‐ferrocenylidene‐2‐oxindole: Synthesis, characterization, electrochemical and antimicrobial evaluation

Cited by 15 publications

References 63 publications

Metal Complexes as Antifungals? From a Crowd-Sourced Compound Library to the First In Vivo Experiments

Metal Complexes as Antifungals? From a Crowd-Sourced Compound Library to the First In Vivo Experiments

Metal Complexes as Antifungals? – From a Crowd-Sourced Compound Library to First In Vivo Experiments

Click approach to the novel 1,2,3-triazolium phosphotungstate organic–inorganic hybrids for the highly promoted synthesis of spirooxindoles

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