Synthesis of new sulfonylamide derivatives of isoxazole via ring-closing metathesis

The QSAR models previously created by the OCHEM web platform were used for the research and design of novel isoxazole derivatives as antimicrobial agents. Based on the created virtual set of promising isoxazole derivatives, a number of potential antibacterial agents were selected for synthesis and further research. A convenient synthetic sequence for obtaining initial isoxazole-containing sulfonylamides and preparative methods for the synthesis of target sulfonylamides of the isoxazole series, in particular, using ring-closing metathesis reactions, were worked out. The results of in vitro antimicrobial activity evaluation of synthesized compounds with predicted high activity showed that a series of isoxazole-containing sulfonylamides are promising antimicrobial agents with a wide spectrum of antibacterial action, especially against multidrug-resistant E. coli, A. baumannii and S. aureus bacterial pathogens. In vivo assessment of the acute toxicity of the studied compounds on the D. magna as a known biosensor proved that most of the studied isoxazole derivatives can be attributed to the class of slightly toxic substances according to the classification developed by Passino and Smith for hydrobionts

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Ring closing metathesis strategies to isoxazole containing thiadiazepines

Pavluik

Bezugly

Kashkovsky

2019

Fr. Ukr. J. Chem.

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Cyclic sulfamides are attractive molecules with potential application in medical chemistry. It is known that thiadiazepine-containing derivatives demonstrate promising value in the development of protease inhibitors such as HIV protease, serine protease and metaloprotease. We demonstrate here a comfortable synthetic sequence to symmetric thiadiazepines containing isoxazole substitutents. The structure of the obtained substances was confirmed by 1H, 13C NMR spectroscopy.

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Synthesis of new sulfonylamide derivatives of isoxazole via ring-closing metathesis

Cited by 4 publications

References 6 publications

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2015

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2015

Isoxazole-containing sulfanilamides as new antibacterial agents: in silico study, synthesis and in vitro evaluation

Ring closing metathesis strategies to isoxazole containing thiadiazepines

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