Azole

An azole is a class of five-membered nitrogen heterocyclic ring compounds containing at least one other noncarbon atom, nitrogen, sulfur or oxygen. The parent compounds are aromatic and have two double bonds; 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.