Chemistry Heterocyclic Building Blocks Oxadiazoles
Oxadiazoles belong to the azole family of heterocyclic aromatic compounds and have the molecular formula C2H2N2O. There exist four oxadiazole isomers, 1,2,3-isomer, 1,2,4-Oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole.
Several pharmaceutical drugs, including raltegravir, butalamine, fasiplon, oxolamine, and pleconaril, contain 1,2,4-oxadiazole, 1,2,5-oxadiazole, or 1,3,4-oxadiazole. The 1,2,3-isomer is prone to ring-opening and forms the diazoketone tautomer, but it can be found in the uncommon sydnone motif.
Oxadiazoles are used in two ways in pharmacology: as a crucial component of the pharmacophore or as a planar aromatic linker that positions substituents correctly and adjusts molecular properties.
There are various regioisomeric forms of oxadiazoles, which are organic heteroaromatic rings comprised of a five-membered structure with two nitrogen atoms and one oxygen atom.
Among the four isomers that exist, the 1,3,4-oxadiazole isomer is the most commonly utilized for diverse applications. The derivatives of 1,3,4-oxadiazole display a broad spectrum of biological properties, such as anti-cancer, anti-inflammatory, analgesic, anticonvulsant, and anti-HIV activities.
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5-(Piperidin-4-yl)-1,3,4-oxadiazol-2(3H)-one hydrochloride
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5-[3-(Trifluoromethyl)phenyl]-3H-1,3,4-oxadiazol-2-one
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4-(1H-Benzo[d]imidazol-2-yl)-1,2,5-oxadiazol-3-amine
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(S)-tert-Butyl (1-(5-mercapto-1,3,4-oxadiazol-2-yl)ethyl)carbamate
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Ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-1,3,4-oxadiazole-2-carboxylate
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5-Methyl-3-(2-oxopropyl)-1,3,4-oxadiazol-2(3H)-one
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3-[4-(Methylsulfonyl)phenyl]-5-(1-boc-4-piperidyl)-1,2,4-oxadiazole