Abstract
Five-membered 1,2,4-oxadiazole heterocyclic ring has received considerable attention because of its unique bioisosteric properties and an unusually wide spectrum of biological activities. Thus, it is a perfect framework for the novel drug development. After a century since the 1,2,4-oxadiazole have been discovered, the uncommon potential attracted medicinal chemists’ attention, leading to the discovery of a few presently accessible drugs containing 1,2,4-oxadiazole unit. It is worth noting that the interest in a 1,2,4-oxadiazoles’ biological application has been doubled in the last fifteen years. Herein, after a concise historical introduction, we present a comprehensive overview of the recent achievements in the synthesis of 1,2,4-oxadiazole-based compounds and the major advances in their biological applications in the period of the last five years as well as brief remarks on prospects for further development.
Highlights
Oxadiazoles are five-membered heterocyclic compounds containing one oxygen and two nitrogen atoms
In 2017 Baykov et al published a study on the first one-pot synthetic procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles at room temperature (RT) from corresponding amidoximes and carboxylic acids methyl or ethyl esters in the superbase medium NaOH/DMSO (Scheme 1) [44]
Summarizing, alkynyl linker replacement with 1,2,4-oxadiazole heterocycle enhanced the biological activity of derivatives against the Rearranged during Transfection (RET) enzyme, their further development may lead to the discovery of novel Ponatinib-like drugs with no adverse effects
Summary
Oxadiazoles are five-membered heterocyclic compounds containing one oxygen and two nitrogen atoms (historically, they were known as furadiazoles). In 2017 Baykov et al published a study on the first one-pot synthetic procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles at room temperature (RT) from corresponding amidoximes and carboxylic acids methyl or ethyl esters in the superbase medium NaOH/DMSO (Scheme 1) [44] This synthetic approach led to obtain diverse oxadiazole analogs isolable via simple purification protocol, in moderate to long reaction time (4–24h) with poor to excellent yields (11–90%). Despite quite a large number of synthetic methods of 1,2,4-oxadiazoles, low yields, long reaction times, an usage of volatile and toxic organic solvents, purification difficulties and a presence of active groups in the structure of reagents (e.g., –NH2, –OH) often limit their application. We hope that this kind of synthetic approach, due to its advantages, will find application in the efficient and environmentally friendly synthesis of the 1,2,4 oxadiazole based compounds in the near future
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
