Synthesis of 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-Derived Dipeptidomimetics

Fluorinated heterocyclic compounds: an assay on the photochemistry of some fluorinated 1-oxa-2-azoles: an expedient route to fluorinated heterocycles

“…On the basis of the above photoreactivities, we now looked at the photochemical behavior of some fluorinated 1,2,4-oxadiazoles. In this context, we wish to note that in the last years, 1,2,4-oxadiazole derivatives have been receiving much attention by virtue of their pharmaceutical applications [32][33][34][35][36][37][38][39][40]. In this paper, we will consider the photochemistry of 3-amino-5-perfluoroalkyl-and 3-amino-5-polyfluorophenyl-1,2,4-oxadiazoles in view of developing methodologies for the synthesis of the corresponding fluorinated ring isomers, namely the 1,3,4-oxadiazoles.…”

CVT-4325: a potent fatty acid oxidation inhibitor with favorable oral bioavailability

“…In particular, oxadiazoles have been used extensively as amide surrogates in the peptide mimetic area, [12][13][14][15] and even in the adenosine field, as a 5 0 -amide surrogate of 5 0 -N-ethylcarboxamide adenosine (NECA). 16 Based on previous SAR of the anilide series, 7 the para position of the 5-phenyl-1,2,4-oxadiazoles 4-7, and the 3-phenyl-1,2,4-oxadiazoles 8-11 was substituted by either a lipophilic or electron withdrawing group (EWG).…”

“…The para-trifluoromethyl 5-phenyl-1,2,4-oxadiazole 7 had the best combination of palmCoA inhibitory activity and metabolic stability (Table 1). A brief exploration of the SAR of the 2-phenyl-1,3,4-oxadiazole series with respect to para-t-butyl, para-chloro, and para-trifluoromethyl (12)(13)(14) demonstrated that this series is less active in the palmCoA assay than either 1,2,4-oxadiazole series (i.e., 3-phenyl and 5-phenyl). In general, within the oxadiazole series explored, the following trend was observed with respect to palmCoA inhibition: 5-phenyl-1,2,4-oxadiazole > 3-phenyl-1,2,4-oxadiazole > 2-phenyl-1,3,4-oxadiazole.…”

Green Approach Towards Synthesis of 3-Substituted-5-Carbonylmetyl-1,2,4-Oxadiazoles Without Any Solvent and Catalyst via Transamidoximation.

“…1,2,4-Oxadiazoles are amazing classes of N-heterocyclic compounds showing their broad spectrum of valuable promising biological activities, such as muscarinic agonists, 4 serotoninergic (5-HT3) antagonists, 5 benzodiazepine receptor agonists, 6 dopamine ligands, 7 inhibitors of monoamine oxidase, 8 sphingosine-1-phosphate-1 (S1P 1 ) receptor agonist 9 can say that 1,2,4-oxaziazole core unit have been explored in past years. 1,2,4-Oxadiazoles have often been used as hydrolysis-resisting bioisosteric replacements for esters and amides 10 and as dipeptide mimetics 11 Bearing in mind the noteworthy relevancies in the fields of medicinal, biological and synthetic organic chemistry, there has been marvelous curiosity in developing efficient procedures for the synthesis of 1,2,4-oxadiazoles and quite number of synthetic procedures have been accounted in the literature for the synthesis of 1,2,4-oxadiazoles derivatives, which include the reaction of amidoxime with activated carboxylic acid derivatives such as acid chlorides, 12 fluorides, 13 anhydrides (BOP-Cl), 14 or active esters 15 using coupling reagents like, DCC, 16 DIC/HOBt, 17 TBTU, 18 CDI. 19 Besides this, metal catalysts, 20 TBAF, 21 microwave technique, 22 NaH, 23 NaOMe, 24 K 2 CO 3 25 and condensation of malonic diesters with amidoximes under neutral and solvent-free conditions 26 were also reported.…”