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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2-(5-Phenyl-1,2,4-oxadiazol-3-yl)morpholine hydrochloride
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2-(4-Chlorophenyl)-N-(4-(5-(furan-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)acetamide
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(4-Amino-1,2,5-oxadiazol-3-yl)methanol
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2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole
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3-(4-(Methylthio)phenyl)-1,2,4-oxadiazol-5-amine
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2-(4-Methoxyphenyl)-5-(1-methyl-1H-indol-3-yl)-1,3,4-oxadiazole
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Ethyl 5-(aminomethyl)-1,3,4-oxadiazole-2-carboxylate 2,2,2-trifluoroacetate
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5-Methyl-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,2,4-oxadiazole
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Benzo[c][1,2,5]oxadiazol-5-ylboronic acid
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(4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenyl)boronic acid
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2-Methyl-5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,4-oxadiazole
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(3-(5-Methyl-1,3,4-oxadiazol-2-yl)phenyl)boronic acid
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2-(3-Methyl-1,2,4-oxadiazol-5-yl)acetic acid