Design, synthesis, and biological activity of novel 2‐(pyridin‐3‐yl)ethan‐1‐one oxime ethers bearing adamantane moiety

Liu, Si; Qian, Ping; Wan, Fuxian; Shi, Yanhua; Jiang, Lin

doi:10.1002/jccs.201800259

Cited by 11 publications

(5 citation statements)

References 17 publications

(11 reference statements)

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“…A 2-aminoadamantylcontaining derivative of pyrrolopyridine known as Peficitinib is used for rheumatoid arthritis treatment [90], and Cu(II) complexes of certain adamantane-substituted pyridines possess anticancer activity [91]. Derivatives of 2-aminopyridine with adamantane fragments were shown to inhibit 11β-hydrosteroid dehydrogenase 11β-HSD1 [92][93][94], and adamantane derivatives of three-substituted pyridine act as antifungal [95] and antinicotinic [96] agents. A great variety of methods exists to introduce heteroaromatic moieties in the adamantanecontaining compounds.…”

Section: Cui-catalyzed Heteroarylation Of Adamantane-containing Aminesmentioning

confidence: 99%

Recent Achievements in the Copper-Catalyzed Arylation of Adamantane-Containing Amines, Di- and Polyamines

et al. 2023

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Rapid development of the copper-catalyzed amination of aryl halides in the beginning of the 21st century, known as the Renaissance of the Ullmann chemistry, laid foundations for the use of this method as a powerful tool for the construction of the C(sp2)-N bond and became a rival of the Buchwald–Hartwig amination reaction. Various applications of this approach are well-documented in a number of comprehensive and more specialized reviews, and this overview in the form of a personal account of the Cu-catalyzed arylation and heteroarylation of the adamantane-containing amines, and di- and polyamines, covers a more specific area, showing the possibilities of the method and outlining general regularities, considering reagents structure, copper source and ligands, scope, and limitations. The material of the last decade is mainly considered, and recent data on the application of the unsupported copper nanoparticles and possibilities of the Chan-Lam reaction as an alternative to the use of aryl halides are also discussed.

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Section: Cui-catalyzed Heteroarylation Of Adamantane-containing Aminesmentioning

confidence: 99%

Recent Achievements in the Copper-Catalyzed Arylation of Adamantane-Containing Amines, Di- and Polyamines

et al. 2023

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“…Adamantane derivatives of oxime ethers with a 3-pyridyl substituent 24a-c , developed by Liu et al [ 27 ], are compounds with the high antifungal activity. Compounds 24a and 24b ( Figure 4 ) show high activity against S. sclerotiorum .…”

Section: Oxime Ethers With An Antifungal Activitymentioning

confidence: 99%

A Review of Biologically Active Oxime Ethers

et al. 2023

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Oxime ethers are a class of compounds containing the >C=N-O-R moiety. The presence of this moiety affects the biological activity of the compounds. In this review, the structures of oxime ethers with specific biological activity have been collected and presented, and bactericidal, fungicidal, antidepressant, anticancer and herbicidal activities, among others, are described. The review includes both those substances that are currently used as drugs (e.g., fluvoxamine, mayzent, ridogrel, oxiconazole), as well as non-drug structures for which various biological activity studies have been conducted. To the best of our knowledge, this is the first review of the biological activity of compounds containing such a moiety. The authors hope that this review will inspire scientists to take a greater interest in this group of compounds, as it constitutes an interesting research area.

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“…Oxime ether has been extensively used as an active group in the structural optimization of agrochemical-related compounds. − The commercial pesticides trifloxystrobin, cymoxanil, and enestroburin, also pictured in Figure , are successful oxime ether fungicides widely used in a variety of field crops . In this study, we designed the 3-position of coumarin containing an oxime ether group, evaluated the antifungal activity, and studied the relationship between the molecular structure and biological activity of oxime ether coumarin derivatives via three-dimensional quantitative structure–activity relationship (3D-QSAR) modeling.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Antifungal Activity, and 3D-QASR of Novel Oxime Ether-Containing Coumarin Derivatives as Potential Fungicides

Dai,

Wang,

Teng

et al. 2024

J. Agric. Food Chem.

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Structural modification of natural products is an effective approach for improving antifungal activity and has, therefore, been used extensively in the development of new agrochemical products. In this work, a series of novel coumarin derivatives containing oxime ether structures were designed, synthesized, and evaluated for antifungal activity. Some of the designed compounds exhibited promising antifungal activities against tested fungi, and compounds 4a, 4c, 5a, and 6b had EC 50 values equivalent to those of commercial fungicides. Compound 6b was the most promising candidate fungicide against Rhizoctonia solani (EC 50 = 0.46 μg/mL). In vivo antifungal bioassays suggested that compounds 5a and 6b could serve as novel agricultural antifungals. Furthermore, microscopy demonstrated that compound 6b induced the sprawling growth of hyphae, distorted the outline of cell walls, and reduced mitochondrial numbers. Additionally, the effects of the substituent steric, electrostatic, hydrophobic, and hydrogen-bond fields were elucidated using an accurate and reliable three-dimensional quantitative structure−activity relationship (3D-QSAR) model. The results presented here will guide the discovery of potential novel fungicides for plant disease control in agriculture.

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Design, synthesis, and biological activity of novel 2‐(pyridin‐3‐yl)ethan‐1‐one oxime ethers bearing adamantane moiety

Cited by 11 publications

References 17 publications

Recent Achievements in the Copper-Catalyzed Arylation of Adamantane-Containing Amines, Di- and Polyamines

Recent Achievements in the Copper-Catalyzed Arylation of Adamantane-Containing Amines, Di- and Polyamines

A Review of Biologically Active Oxime Ethers

Design, Synthesis, Antifungal Activity, and 3D-QASR of Novel Oxime Ether-Containing Coumarin Derivatives as Potential Fungicides

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