Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1H-Pyrazoles derivatives

Zhang, Jin; Tan, Da‐Jin; Wang, Tao; Jing, Sisi; Kang, Yang; Zhang, Zunting

doi:10.1016/j.molstruc.2017.07.106

Cited by 20 publications

(5 citation statements)

References 26 publications

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“…Pyrazole derivatives exhibit a wide range of pharmacological activity (Karrouchi et al, 2018), including analgesic (Vijesh et al, 2013), anticancer (Dawood et al, 2013Koca et al, 2013), antidepressant (Mathew et al, 2014), antifungal (Zhang et al, 2017), anti-inflammatory (Badawey & El-Ashmawey, 1998) and antimicrobial (Vijesh et al, 2013) activities. In addition, a range of thiophene-based heterocyclic compounds have been shown to exhibit antimicrobial activity (Mabkhot et al, 2016).…”

Section: Chemical Contextmentioning

confidence: 99%

Two isostructural 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-ones: disorder and supramolecular assembly

et al. 2020

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Two new chalcones containing both pyrazole and thiophene substituents have been prepared and structurally characterized. 3-(3-Methyl-5-phenoxy-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-one, C23H18N2O2S (I), and 3-[3-methyl-5-(2-methylphenoxy)-1-phenyl-1H-pyrazol-4-yl]-1-(thiophen-2-yl)prop-2-en-1-one, C24H20N2O2S (II), are isomorphous as well as isostructural, and in each the thiophene substituent is disordered over two sets of atomic sites having occupancies 0.844 (3) and 0.156 (3) in (I), and 0.883 (2) and 0.117 (2) in (II). In each structure, the molecules are linked into sheets by a combination of C—H...N and C—H...O hydrogen bonds. Comparisons are made with some related compounds.

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Section: Chemical Contextmentioning

confidence: 99%

Two isostructural 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-ones: disorder and supramolecular assembly

et al. 2020

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“…The pyrazole derivatives are an important class of nitrogen-containing five-membered heterocyclic compounds that have attracted much attention from the synthetic community recently [9,10] due to their unique performance in the field of drug and agrochemical research. They exhibit a wide variety of biological activities, including antibacterial, antifungal [11][12][13], anti-inflammatory, anticancer, anti-tubercular, antiviral, and anti-leishmanial activities [14][15][16][17]. To date, many commercial fungicides with a pyrazole moiety have been approved for plant protection (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

“…Molecules 2023, 28, 6279 2 of 12 Oxathiapiprolin and fluoxapiprolin exhibited great control efficacies against pathogenic oomycetes and acted at the oxysterol binding protein, which is a novel binding site [20]. The fungicides with a pyrazole moiety have been applied to manage a variety of diseases in crops, fruits, and vegetables.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group

Zhao,

Sun,

Meng

et al. 2023

Molecules

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On the basis of the three-component synthetic methodology developed by us, a total of twenty-six pyrazole compounds bearing aryl OCF3 were designed and synthesized. Their chemical structures were characterized by 1H and 13C nuclear magnetic resonance and high-resolution mass spectrometry. These compounds were evaluated systematically for antifungal activities in vitro against six plant pathogenic fungi by the mycelium growth rate method. Most of the compounds showed some activity against each of the fungi at 100 μg/mL. Compounds 1t and 1v exhibited higher activity against all the tested fungi, and 1v displayed the highest activity against F. graminearum with an EC50 value of 0.0530 μM, which was comparable with commercial pyraclostrobin. Structure–activity relationship analysis showed that, with respect to the R1 substituent, the straight chain or cycloalkyl ring moiety was a key structural moiety for the activity, and the R2 substituent on the pyrazole ring could have significant effects on the activity. Simple and readily available pyrazoles with potent antifungal activity were obtained, which are ready for further elaboration to serve as a pharmacophore in new potential antifungal agents.

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“…Rh(I)-catalyzed oxidative-coupling of salicylaldehyde with phenylacetylene [34] and Cu(I)catalyzed cyclization of 3-(2-bromophenyl)-3-oxopropanals [35] gave isoflavones. Transition-metalcatalyzed C C bond cross-coupling, such as Negishi coupling by Pd [36] or Ni [37,38] and Suzuki-Miyaura reactions, [39][40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55] were widely applied for the synthesis of isoflavones in recent years. In addition, triarylbismuths were also employed as a coupling partner of 3-iodo or 3-trifloxychromones for Pd-catalyzed cross-coupling.…”

Section: Introductionmentioning

confidence: 99%

Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

Chang

Liu

Peng

et al. 2021

J Chinese Chemical Soc

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Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl 2 (NH 3) 2 /2,2 0-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80 C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO 3 and a higher reaction temperature (120 C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.

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Synthesis, crystal structure, characterization and antifungal activity of 3,4-diaryl-1H-Pyrazoles derivatives

Cited by 20 publications

References 26 publications

Two isostructural 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-ones: disorder and supramolecular assembly

Two isostructural 3-(5-aryloxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1-(thiophen-2-yl)prop-2-en-1-ones: disorder and supramolecular assembly

Design, Synthesis and Antifungal Activities of Novel Pyrazole Analogues Containing the Aryl Trifluoromethoxy Group

Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

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