Microwave-Assisted Synthesis of Anilinocarbonyl Acetylene: A Quick Access to Terminal Alkynes

Jiang, Yu; Han, Chun Mei; Liang, Xue Qiu

doi:10.4028/www.scientific.net/amr.850-851.66

Cited by 1 publication

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References 30 publications

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“…Brown solid; yield: 60.0%; mp 86.2–86.9 °C; 13 C NMR (101 MHz, DMSO- d 6 ): δ 150.8, 133.9, 130.2, 129.1, 128.5, 128.4, 128.0, 78.4, 78.2. The 1 H NMR data were consistent with those in the literature …”

Section: Methodsmentioning

confidence: 99%

Discovery of N-Phenylpropiolamide as a Novel Succinate Dehydrogenase Inhibitor Scaffold with Broad-Spectrum Antifungal Activity on Phytopathogenic Fungi

Zhang

Yang

Zhang

et al. 2023

J. Agric. Food Chem.

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Based on the structural features of both succinate dehydrogenase inhibitors (SDHIs) and targeted covalent inhibitors, a series of N-phenylpropiolamides containing a Michael acceptor moiety were designed to find new antifungal compounds. Nineteen compounds showed potent inhibition activity in vitro on nine species of plant pathogenic fungi. Compounds 9 and 13 showed higher activity on most of the fungi than the standard drug azoxystrobin. Compound 13 could completely inhibit Physalospora piricola infection on apples at 200 μg/mL concentration over 7 days and showed high safety to seed germination and seedling growth of plants at ≤100 μg/mL concentration. The action mechanism showed that 13 is an SDH inhibitor with a median inhibitory concentration, IC 50 , value of 0.55 μg/mL, comparable with that of the positive drug boscalid. Molecular docking studies revealed that 13 can bind well to the ubiquinone-binding region of SDH by hydrogen bonds and undergoes π−alkyl interaction and π−cation interaction. At the cellular level, 1 as the parent compound could destruct the mycelial structure of P. piricola and partly dissolve the cell wall and/or membrane. Structure−activity relationship analysis showed that the acetenyl group should be a structure determinant for the activity, and the substitution pattern of the phenyl ring can significantly impact the activity. Thus, Nphenylpropiolamide emerged as a novel and promising lead scaffold for the development of new SDHIs for plant protection.

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Section: Methodsmentioning

confidence: 99%

Discovery of N-Phenylpropiolamide as a Novel Succinate Dehydrogenase Inhibitor Scaffold with Broad-Spectrum Antifungal Activity on Phytopathogenic Fungi

Zhang

Yang

Zhang

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

Microwave-Assisted Synthesis of Anilinocarbonyl Acetylene: A Quick Access to Terminal Alkynes

Abstract: A facile synthesis of anilinocarbonyl acetylene was achieved in a microwave-assisted condition via condensation of anilines and propiolic acid. The reactions can be completed smoothly within 10 minutes at 30 °C, producing terminal alkynes with excellent yields.

Cited by 1 publication

References 30 publications

Discovery of N-Phenylpropiolamide as a Novel Succinate Dehydrogenase Inhibitor Scaffold with Broad-Spectrum Antifungal Activity on Phytopathogenic Fungi

Discovery of N-Phenylpropiolamide as a Novel Succinate Dehydrogenase Inhibitor Scaffold with Broad-Spectrum Antifungal Activity on Phytopathogenic Fungi

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