1,2,4-oxadiazole: A Brief Review from the Literature About the Synthesis and Pharmacological Applications

Abstract

Este trabalho contempla uma breve revisão da literatura, empregando os periódicos das bases de dados Scielo, Sciencedirect e ACS, sobre os métodos mais utilizados para síntese do anel 1,2,4-oxadiazólico, destacando suas vantagens e desvantagens. Foi realizada também uma pesquisa sobre as principais funções deste grupamento, sua ação no tratamento de doenças, os testes realizados para a confirmação das ações farmacológicas e os resultados obtidos.Palavras-chave: oxadiazolas; síntese; farmacologia. ABSTRACT:This work includes a brief literature review, using the periodicals of the Scielo, Sciencedirect and ACS databases, about the most used methods for the synthesis of 1,2,4-oxadiazole ring, highlighting their advantages and disadvantages. It was also done a search in the literature about the main functions of this group, its action in the treatment of diseases, the tests made for the confirmation of the pharmacological actions and the results obtained.

Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery

“…Importantly, the heterocycle demonstrates bioisosteric equivalence with ester and amide moieties due to the possibility of creation specific interaction (e.g., hydrogen bonding). It is a particularly useful alternative when the instability of those groups is observed (e.g., when the hydrolysis may appear) [20,21]. Nowadays, there are a few commercially available drugs containing 1,2,4-oxadiazole nucleus such as Oxolamine, Prenoxdiazine (cough suppressant, Figure 3) Butalamine (vasodilator, Figure 3), Fasiplon (nonbenzodiazepine anxiolytic drug, Figure 3), Pleconaril (antiviral drug, Figure 3), Ataluren (Duchenne muscular dystrophy treatment drug, Figure 3) and Proxazole (a drug used for functional gastrointestinal disorders, Figure 3) [22][23][24].…”

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-based derivatives as multitarget anti-Alzheimer agents

“…50 It is a particularly helpful alternative when ester or amide group instability is noted (for example, when hydrolysis may manifest). 51,52 Several molecules with a wide range of biological activities, including anticancer, anti-inflammatory, anticonvulsant, antiviral, antibacterial, antifungal, antiangiogenic, and analgesic properties, have been identified through extensive exploration of the 1,2,4-oxadiazole heterocycle. 53 It was demonstrated that the 1,2,4-oxadiazole scaffold exhibited inhibitory potency against various receptors such as kappa opioid receptor (KOR), 54 human deacetylase sirtuin 2 (HDSirt2), 55 carbonic anhydrase (CA), 56 histone deacetylase (HDAC), 57 and cyclooxygenase-2 (COX-2).…”

A comprehensive review of recent advances in the biological activities of 1,2,4‐oxadiazoles

“…When the instability of these moieties (such as hydrolysis) is discovered, 1,2,4‐oxadiazole is a highly effective alternative. [ 14,15 ] Fasiplon (a nonbenzodiazepine anxiolytic drug), prenoxdiazine (a cough suppressant), butalamine (a vasodilator), ataluren (a treatment drug for Duchenne muscular dystrophy), proxazole (a drug used for functional gastrointestinal disorders), pleconaril (an antiviral drug), and doxylamine are some of the commercially available drugs that contain the 1,2,4‐oxadiazole nucleus (Figure 2). [ 16–18 ]…”