Azole 1855019 209696906 2008-05-02T14:16:53Z Rossenmatev 1014786 /* Uses */ An '''azole''' is a class of five-membered [[nitrogen]] [[heterocyclic]] ring compounds containing at least one other noncarbon atom, nitrogen, sulfur or oxygen.<ref name=Eicher> {{cite book | author = Eicher, T.; Hauptmann, S. | title = The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications | publisher = Wiley-VCH | date = 2nd ed. 2003 | location = | pages = | id = ISBN 3527307206}} </ref> The parent compounds are [[aromatic]] and have two [[double bond]]s; there are successively reduced analogs (azolines and azolidines) with less. Names of azoles maintain the prefix upon [[reduction]] (such as [[pyrazoline]], [[pyrazolidine]]), except for [[pyrrole]], which has no -azole suffix and is reduced to [[pyrroline]] and [[pyrrolidine]]. ==Examples== The azoles include: * 1 nitrogen **[[pyrrole]] * 2 or more nitrogen atoms **[[pyrazole]] **[[imidazole]], included in [[histidine]] **[[triazole]], included in [[Ribavirin]] **[[tetrazole]] * 1 nitrogen atom and 1 oxygen atom ** [[oxazole]] ** [[isoxazole]] * 1 nitrogen atom and 1 sulfur atom ** [[thiazole]] ** [[isothiazole]] A "dioxole" is a similar compound with two oxygen atoms in a five membered ring. [[Dioxolane]] is a derivative of dioxole. ==Uses== Many azoles are used as [[antifungal]] drugs ([[azole antifungals]]), inhibiting the fungal enzyme [[14α-demethylase]] which produces [[ergosterol]] (an important component of the fungal plasma membrane). ==External links== * {{MeshName|Azoles}} * [http://www.chem.qmul.ac.uk/iupac/hetero/HW.html Nomenclature, IUPAC] ==References== <references/> [[Category:Azoles|*]] [[Category:Heterocyclic compounds|Heterocyclic compounds]] [[es:Azol]] [[it:Azoli]] [[ja:アゾール]]