Azole
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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]]