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.

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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.

References