Fluorine-containing pyrazoles and their condensed derivatives: Synthesis and biological activity

Lipunova, G. N.; Носова, Э. В.; Charushin, Valery N.; Чупахин, О. Н.

doi:10.1016/j.jfluchem.2015.03.011

Cited by 30 publications

(10 citation statements)

References 54 publications

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“…Taking into account that fluorinated heterocycles [31][32][33][34], including pyrazoles [31,35,36], are of great significance for various medicinal and agricultural applications, the development of new methods for the construction of fluorine-containing organic molecules combined with the 1,4-quinone moiety can be considered as a challenging problem of current organic synthesis. Thus, the main goal of the present study was to check the course of [3 + 2]-cycloaddition reactions of electron-deficient CF 3 -substituted nitrile imines 7 with 1,4-naphthoquinone (1a) and 1,4-anthraquinone (1b), which were selected as model dipolarophiles.…”

Section: Introductionmentioning

confidence: 99%

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

Utecht-Jarzyńska¹,

Nagła²,

Mlostoń³

et al. 2021

Beilstein J. Org. Chem.

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In-situ-generated N-aryl nitrile imines derived from trifluoroacetonitrile efficiently react with polycyclic 1,4-quinones, yielding fused pyrazole derivatives as the exclusive products. The reactions proceed via the initially formed [3 + 2]-cycloadducts, which undergo spontaneous aerial oxidation to give aromatized heterocyclic products. Only for 2,3,5,6-tetramethyl-1,4-benzoquinone, the expected [3 + 2]-cycloadduct exhibited fair stability and could be isolated in moderate yield (53%). The presented method offers a straightforward access to hitherto little known trifluoromethylated polycyclic pyrazoles. All products were isolated as pale colored solids with medium-intensity absorption maxima in the range of 310–340 nm for naphthoquinone-derived products and low-intensity bands in the visible region (≈400 nm) for the anthraquinone series.

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Section: Introductionmentioning

confidence: 99%

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

Utecht-Jarzyńska¹,

Nagła²,

Mlostoń³

et al. 2021

Beilstein J. Org. Chem.

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“…Given that regioselective approaches for obtaining trifluoromethyl‐containing pyrazoles are continuously being sought for biological/pharmacological purposes, [ 46–51 ] synthetic methods associated with these structures have been, and still remain, of great interest. [ 52–55 ] Using a similar approach, trifluoromethyl β‐enamino diketones 9 were used in a regio‐ and chemoselective cyclocondensation reaction with phenylhydrazine (Scheme 12).…”

Section: Synthesis Of Pyrazolesmentioning

confidence: 99%

The Wonderful World of β‐Enamino Diketones Chemistry

et al. 2020

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The simple preparation and functionalization of oxa/aza heterocycles requires new and efficient starting materials to be discovered so that regioselective methodologies with a wide range of applications in organic synthesis can be developed. With this in mind, β‐enamino diketones have emerged as a suitable building block for preparing the most diverse (poly)heterocyclic systems, through cyclocondensation or cycloaddition reactions. This review compiles all the reactions that have been conducted using these starting materials, ever since they were first disclosed in 1980.

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“…Heterocyclic compounds have been the focus of research because of their high specificity, high activity, low dose, and low toxicity ( Lamberth, 2013 ). Among them, azole, such as pyrazole, imidazole, oxazole, and other important members of five-member heterocyclic system, exist in many products with physiological active structure, are widely used in biology, medicine, industry and other fields, and show unique properties ( Küçükgüzel and Şenkardeş, 2015 ; Lipunova et al, 2015 ; Guerrero-Pepinosa et al, 2021 ; Rulhania et al, 2021 ; Parikh et al, 2022 ). Many azole derivatives had become important drugs, which can be used in the treatment of antifungal ( Lipunova et al, 2015 ; Wei et al, 2018 ; Guerrero-Pepinosa et al, 2021 ; Zhang et al, 2022 ), antitumor ( Küçükgüzel and Şenkardeş, 2015 ; Silva-Ortiz et al, 2016 ; Titi et al, 2020 ; Balaraju et al, 2021 ; Oskuei et al, 2021 ), antituberculosis ( Xu et al, 2017 ; Fan et al, 2018 ; Negalurmath et al, 2019 ), hypoglycemic ( Al-Harbi et al, 2013 ), anti-inflammatory ( Selvam et al, 2014 ), and other diseases, especially in pesticides, often used as fungicides and herbicides ( Price et al, 2015 ; Shevaldina et al, 2019 ).…”

Section: Introductionmentioning

confidence: 99%

Development of 1,3,4-Oxadiazole Derived Antifungal Agents and Their Application in Maize Diseases Control

Zhang

et al. 2022

Front. Plant Sci.

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Maize is an important food crop and its fungal disease has become a limiting factor to improve the yield and quality of maize. In the control of plant pathogens, commercial fungicides have no obvious effect on corn diseases due to the emergence of drug resistance. Therefore, it is of great significance to develop new fungicides with novel structure, high efficiency, and low toxicity to control maize diseases. In this paper, a series of 1,3,4-oxadiazole derivatives were designed and synthesized from benzoyl hydrazine and aromatic aldehydes through condensation and oxidation cyclization reaction. The antifungal activity of oxadiazole derivatives against three maize disease pathogens, such as Rhizoctonia solani (R. solani), Gibberella zeae (G. zeae), and Exserohilum turcicum (E. turcicum), were evaluated by mycelium growth rate method in vitro. The results indicated that most of the synthesized derivatives exhibited positive antifungal activities. Especially against E. turcicum, several compounds demonstrated significant antifungal activities and their EC50 values were lower than positive control carbendazim. The EC50 values of compounds 4k, 5e, and 5k were 50.48, 47.56, 32.25 μg/ml, respectively, and the carbendazim was 102.83 μg/ml. The effects of active compounds on E. turcicum microstructure were observed by scanning electron microscopy (SEM). The results showed that compounds 4k, 5e, and 5k could induce the hyphae of E. turcicum to shrink and collapse obviously. In order to elucidate the preliminary mechanism of oxadiazole derivatives, the target compounds 5e and 5k were docked with the theoretical active site of succinate dehydrogenase (SDH). Compounds 5e and 5k could bind to amino acid residues through hydrophobic contact and hydrogen bonds, which explained the possible mechanism of binding between the inhibitor and target protein. In addition, the compounds with antifungal activities had almost no cytotoxicity to MCF-7. This study showed that 1,3,4-oxadiazole derivatives were worthy for further attention as potential antifungal agents for the control of maize diseases.

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Fluorine-containing pyrazoles and their condensed derivatives: Synthesis and biological activity

Cited by 30 publications

References 54 publications

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

The Wonderful World of β‐Enamino Diketones Chemistry

Development of 1,3,4-Oxadiazole Derived Antifungal Agents and Their Application in Maize Diseases Control

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