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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3-(4-Methoxyphenyl)-5-(piperidin-3-yl)-1,2,4-oxadiazole hydrochloride
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1-[(3-Methyl-1,2,4-oxadiazol-5-yl)methyl]-6-oxo-1,6-dihydropyridine-3-carboxylic acid
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Methyl 3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)benzoate
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Ethyl 3-methyl-1,2,4-oxadiazole-5-carboxylate
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(S)-3-methyl-5-(2-pyrrolidinyl)-1,2,4-oxadiazole
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Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate
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(5-Methyl-1,2,4-oxadiazol-3-yl)methanamine hydrochloride
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Ethyl 3-(4-chlorophenyl)-1,2,4-oxadiazole-5-carboxylate
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2-(5-(Chloromethyl)-1,2,4-oxadiazol-3-yl)phenol
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{2-[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]ethyl}amine hydrochloride
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Methyl 3-(2-((5-(3,5-dimethoxyphenyl)-1,3,4-oxadiazol-2-yl)thio)acetamido)benzoate
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5-Cyclopropyl-1,2,4-oxadiazole-3-carboxylic acid