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Issue 26, 2018
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Valdecoxib vs. borazavaldecoxib: isoxazole BN/CC isosterism as a case study in designing and stabilizing boron heterocycles

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Abstract

A comprehensive study on the preparation, hydrolytic stability, and the structural and spectrophotometric properties of 1,2,4,5-oxadiazaboroles is presented by way of a comparison between the NSAID drug valdecoxib (1) and its unprecedented B–N isostere, borazavaldecoxib (2). Knowledge gained from this study was employed in the design of oxadiazaborate salts, a novel class of tetrahedral boron heterocycles displaying good stability in aqueous conditions with promising antifungal and antibacterial properties.

Graphical abstract: Valdecoxib vs. borazavaldecoxib: isoxazole BN/CC isosterism as a case study in designing and stabilizing boron heterocycles

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Article information


Submitted
28 Apr 2018
Accepted
08 Jun 2018
First published
08 Jun 2018

Org. Biomol. Chem., 2018,16, 4849-4856
Article type
Paper

Valdecoxib vs. borazavaldecoxib: isoxazole BN/CC isosterism as a case study in designing and stabilizing boron heterocycles

M. Boghi and D. G. Hall, Org. Biomol. Chem., 2018, 16, 4849
DOI: 10.1039/C8OB00998H

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