Design and synthesis of novel cylopentapyrazoles bearing 1,2,3-thiadiazole moiety as potent antifungal agents

Giray, Betul; Karadağ, Ayşe Esra; İpek, Özgecan Şavluğ; Pekel, Hanife; Güzel, Mustafa; Küçük, Hatice Başpınar

doi:10.1016/j.bioorg.2019.103509

Cited by 13 publications

(8 citation statements)

References 40 publications

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“…To our ongoing efforts in the preparation of various heterocyclic pharmacological active motifs, [27][28][29] we herein synthesized new 2,5-disubstituted 1,3,4-oxadiazoles from their precursors N-acyl hydrazones with molecular iodine. However, to the best of our knowledge, molecular iodine-mediated oxidative cyclization for the synthesis of 2,5-disubstituted 1,3,4oxadiazole compounds from 2-arenoxybenzaldehydes and various substituted hydrazides has not yet been reported.…”

Section: Chemistryselectmentioning

confidence: 99%

An efficient approach to access 2,5‐disubstituted 1,3,4‐oxadiazoles by oxidation of 2‐arenoxybenzaldehyde N‐acyl hydrazones with molecular iodine

et al. 2022

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An oxidative cyclization of 2‐arenoxybenzaldehyde N‐acyl hydrazones 3 a–o was employed to synthesize new 2,5‐disubstituted 1,3,4‐oxadiazole compounds 4 a–d, 4 f–i, 4 k–n. This method involves oxidative cyclization of 2‐arenoxybenzaldehyde N‐acyl hydrazones 3 a–o with molecular iodine mediated catalysis in which potassium carbonate served as a base. Characterization of all the synthesized novel compounds involved, proton and carbon NMR, mass spectrometry, and CHN elemental analysis. The synthesis of novel 2,5‐disubstituted 1,3,4‐oxadiazoles may display potential to provide pharmacologically important heterocyclic compounds.

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Section: Chemistryselectmentioning

confidence: 99%

An efficient approach to access 2,5‐disubstituted 1,3,4‐oxadiazoles by oxidation of 2‐arenoxybenzaldehyde N‐acyl hydrazones with molecular iodine

et al. 2022

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“…Over the past few years, compounds containing thiazole and/or thiadiazole scaffold are attractive to medicinal chemistry due to their unique chemical properties and diversity of the biological activities [20–25] . Therefore, they have therapeutic effects against several diseases such as antimalarial, antimicrobial, antiproliferative agents and anti‐inflammatory [26–30] besides their significant with various fungicidal activities [31,32] . In addition, many scientific reported have also demonstrated that the sulfonamide moiety itself possess interesting pharmacological activities and therapeutic functions [33,34]…”

Section: Introductionmentioning

confidence: 99%

“…[20][21][22][23][24][25] Therefore, they have therapeutic effects against several diseases such as antimalarial, antimicrobial, antiproliferative agents and anti-inflammatory [26][27][28][29][30] besides their significant with various fungicidal activities . [31,32] In addition, many scientific reported have also demonstrated that the sulfonamide moiety itself possess interesting pharmacological activities and therapeutic functions. [33,34] Recently, numerous studies indicated the importance of a molecular hybridization strategy based on incorporating two or more bioactive moieties into a single molecule has displayed a simple, potent effective, and promising approach to find out…”

Section: Introductionmentioning

confidence: 99%

Investigation of Novel Mucorales Fungal Inhibitors: Synthesis, In‐Silico Study and Anti‐Fungal Potency of Novel Class of Coumarin‐6‐Sulfonamides‐Thiazole and Thiadiazole Hybrids

et al. 2022

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A series of coumarin‐6‐sulfonamides derivatives bearing a thiazole and thiadiazole scaffold were synthesized, their chemical structures were inferred from correct spectral and microanalytical data. All the newly synthesized compounds have been screened for their ability to prevent the proliferation of Mucor racemosus, Syncephalastrum racemosum in vitro. The most potent compounds were chosen to determine the MIC value in compared to the standard antifungal agent (Posaconazole). Remarkably, an excellent anti‐mucormycosis was obtained by compounds known as 8 d, and 8 d with MIC value close to that observed by the standard Posaconazole. Amolecular. Docking study was performed where compounds 3, 5 a, 5 d, 8 d, 8 e, 10 c and 10 e were docked against the fungal enzyme sterol 14‐alpha demethylase (CYP51) “PDB id: 5FSA”. In silico, compounds 8 d & 8 e showed the best docking by forming 3H bonds and free binding energy (12.2 & 12 K cal/mol) close to the binding energy (12.2 K cal/mol) of the co‐crystalized inhibitor (posconazol. From wet lab and dry lab results, one can recommend compounds 8 d & 8 e for further antifungal drug development.

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“…Currently, the prevention and treatment of phytopathogenic fungi rely mainly on synthetic fungicides . However, long-term uncontrolled application of fungicides has caused negative consequences including environmental pollution, pesticide residues, and increased fungal resistance. − Therefore, it is urgent to discover novel fungicide agents with less toxicity and that are effective to face the challenge …”

Section: Introductionmentioning

confidence: 99%

Novel Pyrazolo[3,4-d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation

Cheng

Wang

et al. 2021

J. Agric. Food Chem.

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Plant pathogenic fungi seriously threaten agricultural production. There is an urgent need to develop novel fungicides with low toxicity and high efficiency. In this study, we designed and synthesized 44 pyrazolo[3,4-d]pyrimidin-4-one derivatives and evaluated them for their fungicidal activities. The bioassay data revealed that most of the target compounds possessed moderate to high in vitro antifungal activities. Especially compound g22 exhibited remarkable antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.25 mg/L, close to that of commercial fungicide boscalid (EC50 = 0.96 mg/L) and fluopyram (EC50 = 1.91 mg/L). Moreover, compound g22 possessed prominent protective activity against S. sclerotiorum in vivo for 24 h (95.23%) and 48 h (93.78%), comparable to positive control boscalid (24 h (96.63%); 48 h (93.23%)). Subsequent studies indicated that compound g22 may impede the growth and reproduction of S. sclerotiorum by affecting the morphology of mycelium, destroying cell membrane integrity, and increasing cell membrane permeability. In addition, the application of compound g22 did not injure the growth or reproduction of Italian bees. This study revealed that compound g22 is expected to be developed for efficient and safe agricultural fungicides.

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Design and synthesis of novel cylopentapyrazoles bearing 1,2,3-thiadiazole moiety as potent antifungal agents

Cited by 13 publications

References 40 publications

An efficient approach to access 2,5‐disubstituted 1,3,4‐oxadiazoles by oxidation of 2‐arenoxybenzaldehyde N‐acyl hydrazones with molecular iodine

An efficient approach to access 2,5‐disubstituted 1,3,4‐oxadiazoles by oxidation of 2‐arenoxybenzaldehyde N‐acyl hydrazones with molecular iodine

Investigation of Novel Mucorales Fungal Inhibitors: Synthesis, In‐Silico Study and Anti‐Fungal Potency of Novel Class of Coumarin‐6‐Sulfonamides‐Thiazole and Thiadiazole Hybrids

Novel Pyrazolo[3,4-d]pyrimidin-4-one Derivatives as Potential Antifungal Agents: Design, Synthesis, and Biological Evaluation

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