AI Article Synopsis
- A new one-pot method has been developed to synthesize various (1,3,4-oxadiazol-2-yl)anilines using isatins and hydrazides, with molecular iodine as the catalyst.
- This efficient process involves multiple steps, including condensation and ring cleavage, ultimately leading to the formation of a C-O bond in a single reaction.
- The synthesized compounds were tested for their ability to inhibit carbonic anhydrase enzymes, showing promising activity, especially some that are highly selective for the hCA II isoform.
Article Abstract
A practical and transition metal-free one-pot domino synthesis of diversified (1,3,4-oxadiazol-2-yl)anilines has been developed employing isatins and hydrazides as the starting materials, in the presence of molecular iodine. The prominent feature of this domino process involves consecutive condensation, hydrolytic ring cleavage, and an intramolecular decarboxylation, in a one-pot process that leads to the oxidative formation of a C-O bond. Fluorescence properties of some of the representative molecules obtained in this way were studied. The synthesised 2-(1,3,4-oxadiazolo-2-yl)aniline-benzene sulphonamides (8a-o) were screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity. Most of the compounds exhibited low micromolar to nanomolar activity against human (h) isoforms hCA I, hCA II, hCA IV, and XII, with some compounds displaying selective CA inhibitory activity towards hCA II with Ks of 6.4-17.6 nM.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6010027 | PMC |
| http://dx.doi.org/10.1080/14756366.2018.1443447 | DOI Listing |
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