Discovery of an exceptionally potent and selective class of fatty acid amide hydrolase inhibitors enlisting proteome-wide selectivity screening: concurrent optimization of enzyme inhibitor potency and selectivity

Copper‐Mediated C–H Activation of 1,3,4‐Oxadiazoles with 1,1‐Dibromo‐1‐alkenes Using PEG‐400 as a Solvent Medium: Distinct Approach for the Alkynylation of 1,3,4‐Oxadiazoles

“…[1] They are also known to act as ester and amide bioisosters. [2] Certain oxadiazole derivatives have been applied in the development of organic electronics. [3] Consequently, the preparation of these compounds is of considerable importance in organic synthesis.…”

Fatty Acid Amide Hydrolase: From Characterization to Therapeutics

“…Moreover, the potency is strongly dependent on the hydrophobicity of the flexible acyl chain. The inhibitors and their analogues were found to be quite selective towards other serine hydrolases, based on a proteomic assay, the most potent and selective ones being 2-pyridyl-subsituted 1,3,4-oxadiazoles such as compound 2 [76] [77]. In the same family, the inhibitor 3 (OL-135) displayed an exceptional combination of potency (K i ¼ 0.0047 mm towards rat-recombinant FAAH) and in vivo selectivity [72] [78].…”

Synthesis, enzyme kinetics and computational evaluation of N-(β-d-glucopyranosyl) oxadiazolecarboxamides as glycogen phosphorylase inhibitors

“…Following a literature protocol, commercially available benzhydrazide (1) was ethoxalylated to give 2 (Scheme 2) which was closed to ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (3) in 47% yield. 31 Hydrolysis of 3 gave carboxylic acid 4 in 70% yield. 32 Synthesis of 1,2,4-oxadiaz-110 ole-carboxylic acids was also tried from the corresponding ethyl esters, 33 however, we were unable to reproduce the reported hydrolytic step 34 because of opening of the heterocycle.…”