Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides

Du, Shaowu; Lu, Huizhe; Yang, Dongyan; Li, Hong; Gu, Xilin; Wan, Chuan; Jia, Changqing; Wang, Mian; Liu, Xiuyun; Qin, Zhaohai

doi:10.3390/molecules20034071

Cited by 24 publications

(19 citation statements)

References 18 publications

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“…Qin et al [ 88 ] described the synthesis of a novel series of aromatic carboxylic acid amides containing 1 H -indazole moiety based on a bioisosterism approach and evaluation of their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. The preliminary biological results demonstrated that all of the target molecules displayed moderate to good activity against the six kinds of fungi.…”

Section: Biological Applications Of Indazole Derivativesmentioning

confidence: 99%

Recent Advances in Indazole-Containing Derivatives: Synthesis and Biological Perspectives

2018

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Indazole-containing derivatives represent one of the most important heterocycles in drug molecules. Diversely substituted indazole derivatives bear a variety of functional groups and display versatile biological activities; hence, they have gained considerable attention in the field of medicinal chemistry. This review aims to summarize the recent advances in various methods for the synthesis of indazole derivatives. The current developments in the biological activities of indazole-based compounds are also presented.

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Section: Biological Applications Of Indazole Derivativesmentioning

confidence: 99%

Recent Advances in Indazole-Containing Derivatives: Synthesis and Biological Perspectives

2018

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“…The antifungal activity of the synthesized compounds was performed according to previously reported procedures [ 33 ]. The fungicidal activity of the target compounds against R. solani , F. oxysporum , B. cinerea Pers., sunflower sclerotinia rot and rape sclerotinia rot were evaluated using a mycelium growth rate test [ 17 ].…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Antifungal Activity of Novel Aryl-1,2,3-Triazole-β-Carboline Hybrids

et al. 2018

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The copper catalytic azide and terminal alkyne cycloaddition reaction, namely “click chemistry”, gives a new and convenient way to create l,4-disubstitutd-l,2,3-triazoles. In this work, 2-pyrrolecarbaldiminato–Cu(II) complexes were established as efficient catalysts for the three-component 1,3-dipolar cycloaddition reaction of arylboronic acid and sodium azide (NaN3) with terminal alkynes in ethanol at room temperature to 50 °C, 1,4-disubstituted 1,2,3-triazoles were synthesized. Following the optimized protocol, two series of new aryl-1,2,3-triazole-β-carboline hybrids have been designed and synthesized, and the chemical structures were characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometry (HRMS). All of the target compounds were evaluated in vitro for their antifungal activity against Rhizoctorzia solani, Fusarium oxysporum, Botrytis cinerea Pers., sunflower sclerotinia rot, and rape sclerotinia rot by mycelia growth inhibition assay at 50 μg/mL. The antifungal evaluation of the novel hybrids showed that, among the tested compounds, 5a, 5b, 5c, and 9b showed good antifungal activity against sunflower sclerotinia rot. Specifically, compound 9b also exhibited high broad-spectrum fungicidal against all the tested fungi with inhibition rates of 58.3%, 18.52%, 63.07%, 84.47%, and 81.23%. However, for F. oxysporum, all the target compounds showed no in vitro antifungal activities with an inhibition rate lower than 20%. These results provide an encouraging framework that could lead to the development of potent novel antifungal agents.

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“…Three-dimensional molecular structures were built using the SKETCH module in Sybyl 7.3, while structural energy minimization was performed with the Tripos force field until a gradient convergence of 0.05 kcal/(mol A) was achieved. Gasteiger–Hückel charges were calculated and used to construct the CoMFA models [20]. …”

Section: Methodsmentioning

confidence: 99%

Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs

et al. 2018

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For the first time, a novel series of tschimganin analogs were designed, synthesized, and evaluated for their insecticidal and fungicidal activities. Their structures were characterized by 1H-NMR, 13C-NMR and HRMS. Some of these compounds displayed excellent insecticidal and fungicidal activities, suggesting that they have potential to be used as bifunctional agrochemicals. Compound 3d and 3g with electron donating groups showed better inhibitory activity and growth inhibition activity towards Helicoverpa armigera (Hübner). The properties and positions of the substituents on the benzene ring have an important influence on the acaricidal activity of tschimganin analogs. Topomer comparative molecular field analysis (CoMFA) was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds against Tetranychus turkestani Ugarov et Nikolski. It was indicated that higher electronegativity was beneficial for acaricidal activity. Moreover, compound 3r having a 2-hydroxy-3,5- dinitrophenyl moiety displayed a fungicidal spectrum as broad as azoxystrobin against these phytopathogens.

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Synthesis, Antifungal Activity and QSAR of Some Novel Carboxylic Acid Amides

Cited by 24 publications

References 18 publications

Recent Advances in Indazole-Containing Derivatives: Synthesis and Biological Perspectives

Recent Advances in Indazole-Containing Derivatives: Synthesis and Biological Perspectives

Design, Synthesis, and Antifungal Activity of Novel Aryl-1,2,3-Triazole-β-Carboline Hybrids

Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs

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