Synthesis and biological evaluation of polyfluoroalkyl-containing 4-arylhydrazinylidene-isoxazoles as antifungal agents with antioxidant activity

Elkina, Natalia А.; Shchegolkov, Evgeny V.; Burgart, Yanina V.; Agafonova, N. A.; Perminova, A. N.; Герасимова, Н. А.; Махаева, Галина Ф.; Рудакова, Е. В.; Kovaleva, N. V.; Boltneva, Natalia P.; Serebryakova, Olga G.; Borisevich, Sophia S.; Евстигнеева, Н. П.; Зильберберг, Н. В.; Кунгуров, Н. В.; Салоутин, В. И.

doi:10.1016/j.jfluchem.2021.109935

Cited by 4 publications

(1 citation statement)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…have reported a regioselctive synthesis of 4‐arylhydrazinylidene‐3‐polyfluoroalkylisoxazol‐5‐ones 246 and 4‐arylhydrazinylidene‐5‐polyfluoroalkyldihydroisoxazol‐5‐oles 247 via reaction of hydroxylamine 55 with 2‐arylhydrazinylidene‐3‐polyfluoroalkyl‐3‐oxo esters or 2‐arylhydrazinylidene‐3‐polyfluoroalkyl‐1,3‐diketones 144 , respectively (Scheme 80). [166] Dihydroisoxazol‐5‐oles 247 were dehydrated under sulfuric acid to afford 4‐arylhydrazinylidene‐5‐polyfluoroalkylisoxazoles 248 . Biological testing revealed that most of the isoxazolones 246 and dihydroisoxazoles 247 exhibited good antifungal activity against strains of dermatophyte ( Trichophyton family, E. floccosum , and M. canis ; MIC 0.78‐25 μg/kg) and C. ablicans yeast (MIC 25 μg/kg).…”

Section: Trifluoromethyl‐β‐dicarbonyls Based Synthesis Of Heterocyclesmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances the bioactivity by altering pharmacological profile of molecule. Trifluoromethyl‐β‐dicarbonyls have emerged as pivotal building blocks in synthetic organic chemistry due to their facile accessibility, stability and remarkable versatility. Owing to presence of nucleophilic and electrophilic sites, they offer multifunctional sites for the reaction. This review covers a meticulous exploration of their multifaceted role, encompassing an in‐depth analysis of mechanism, extensive scope, limitations and wide‐ranging applications in diverse organic synthesis, covering the literature from the 21st century. This comprehensive review encapsulates the applications of trifluoromethyl‐β‐dicarbonyls and their synthetic equivalents as precursors of complex and diverse heterocyclic scaffolds, fused heterocycles and spirocyclic compounds having medicinal and material importance. Their potent synthetic utility in cyclocondenation reactions with binucleophiles, cycloaddition reactions, C‐C bond formations, asymmetric multicomponent reactions using classical/solvent‐free/catalytic synthesis have been presented. Influence of unsymmetrical trifluoromethyl‐β‐diketones on regioselectivity of transformation is also reviewed. This review will benefit the synthetic and pharmaceutical communities to explore trifluoromethyl‐β‐dicarbonyls as trifluoromethyl building blocks for fabrication of heterocyclic scaffolds having implementation into drug discovery programs in the imminent future.

show abstract

Section: Trifluoromethyl‐β‐dicarbonyls Based Synthesis Of Heterocyclesmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

show abstract

Urea-catalyzed multicomponent synthesis of 4-arylideneisoxazol-5(4H)-one derivatives under green conditions

Haydari

Kiyani

2022

Res Chem Intermed

View full text Add to dashboard Cite

Regioselective synthesis of 2-aryl-5-(polyfluoroalkyl)pyridazin-3-ones based on 2-arylhydrazinylidene 1,3-dicarbonyl compounds

et al. 2023

View full text Add to dashboard Cite

Synthesis and biological evaluation of polyfluoroalkyl-containing 4-arylhydrazinylidene-isoxazoles as antifungal agents with antioxidant activity

Cited by 4 publications

References 64 publications

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Urea-catalyzed multicomponent synthesis of 4-arylideneisoxazol-5(4H)-one derivatives under green conditions

Regioselective synthesis of 2-aryl-5-(polyfluoroalkyl)pyridazin-3-ones based on 2-arylhydrazinylidene 1,3-dicarbonyl compounds

Contact Info

Product

Resources

About