The Current Status of O‐Heterocycles: A Synthetic and Medicinal Overview

Abstract

O-Heterocycles have been explored in the field of medicinal chemistry for a long time, but their significance has not been duly recognised and they are often shunned in favour of N-heterocycles. The design of bioactive molecules for nearly every pathophysiological condition is primarily focused on novel N-heterocycles. The main reasons for such bias include the ease of synthesis and possible mimicking of physiological molecules by N-heterocycles. But considering only this criterion rarely provides breakthrough molecules for a given disease condition, and instead the risks of toxicity or side effects are increased with such molecules. On the other hand, owing to improved synthetic feasibility, O-heterocycles have established themselves as equally potent lead molecules for a wide range of pathophysiological conditions. In the last decade there have been hundreds of reports validating the fact that equally potent molecules can be designed and developed by using O-heterocycles, and these are also expected to have comparably low toxicity. Even so, researchers tend to remain biased toward the use of N-heterocycles over O-heterocycles. Thus, this review provides a critical analysis of the synthesis and medicinal attributes of O-heterocycles, such as pyrones, oxazolones, furanones, oxetanes, oxazolidinones, and dioxolonones, and others, reported in the last five years, underlining the need for and the advantages guiding researchers toward them.

Production of Hydroxy Acids: Selective Double Oxidation of Diols by Flavoprotein Alcohol Oxidase

“…Oxygen‐containing heterocycles (O‐heterocycles) form a class of compounds proven to be relevant in the polymers, fuel, and medical fields . Some of these O‐heterocycles, such as lactones, and in particular 1,4‐dioxan‐2‐one can be used for synthesis of biodegradable polyesters that find countless clinical applications thanks to their biocompatibility and strength properties .…”

Identification of 2‐benzoxazolinone derivatives as lead against molecular targets of diabetic complications

“…Glide was used to perform the docking simulations, while Desmond software working on OPLS_2005 force field was used for molecular dynamics simulations. The protein complex was neutralized by adding Na + ions, and the system was then solvated in orthorhombic box of TIP3P water molecules having a salt concentration of 0.15 M. A temperature of 310 K was maintained using Nose‐Hoover Chain thermostat and a pressure of 1.01 bar using Martyn‐Tobias‐Klein barostat …”

Electrosynthesis of Oxazol‐2(3H)‐Ones and Diaroylhydrazines from 1,2‐Dicarbonyl Compounds and Arenediazonium Salts

“…Oxazol‐2(3 H )‐ones are considered valuable structural motifs in medicinal chemistry due to their low toxicity versus the corresponding N ‐heterocycles . 4,5‐Diphenyloxazolone derivatives have been described as selective cyclooxygenase‐2‐(COX‐2) inhibitors .…”

“…Oxazol-2(3H)-ones are considered valuable structural motifs in medicinal chemistry due to their low toxicity versus the corresponding N-heterocycles. [7] 4,5-Diphenyloxazolone derivatives have been described as selective cyclooxygenase-2-(COX-2) inhibitors. [8] There are also several patents describing oxazolones as inhibitors of streptococcus mutans biofilm formation in the prevention and treatment of dental caries [9] or to enhance the learning rate and extend the memory in rats.…”