Azole

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Class of heterocyclic compounds

title: "Azole" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["azoles", "functional-groups"] description: "Class of heterocyclic compounds" topic_path: "general/azoles" source: "https://en.wikipedia.org/wiki/Azole" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Class of heterocyclic compounds ::

::callout[type=note] the class of compounds ::

Azoles are a class of five-membered heterocyclic compounds containing a nitrogen atom and at least one other non-carbon atom (i.e. nitrogen, sulfur, or oxygen) as part of the ring. |author1=Eicher, T. |author2=Hauptmann, S. | title = The Chemistry of Heterocycles: Structure, Reactions, Synthesis, and Applications | publisher = John Wiley & Sons | date = June 2003 | edition = 2nd | isbn = 3-527-30720-6}} Their names originate from the Hantzsch–Widman nomenclature. The parent compounds are aromatic and have two double bonds; there are successively reduced analogs (azolines and azolidines) with fewer. One, and only one, lone pair of electrons from each heteroatom in the ring is part of the aromatic bonding in an azole. Names of azoles maintain the prefix upon reduction (e.g., pyrazoline, pyrazolidine). The numbering of ring atoms in azoles starts with the heteroatom that is not part of a double bond, and then proceeds towards the other heteroatom.

Imidazole and other five-membered aromatic heterocyclic systems with two nitrogens are extremely common in nature and form the core of many biomolecules, such as histidine.

Compound classes

;N,S compounds Thiazol.svg|Thiazole Isothiazol - Isothiazole.svg|Isothiazole 1,2,3-thiadiazole-2D-skeletal.png |Thiadiazole (1,2,3-Thiadiazole) 1,2,4-thiadiazole-2D-skeletal.png |1,2,4-thiadiazole 1,2,5-Thiadiazole-2D-skeletal.svg |1,2,5-thiadiazole 1,3,4-thiadiazole-2D-skeletal.png |1,3,4-thiadiazole

Use as antifungal agents

::figure[src="https://upload.wikimedia.org/wikipedia/commons/4/4e/Fluconazole_skeletal_formula.svg" caption="Skeletal formula of [[fluconazole]] - an [[antifungal]] medication"] ::

The search for antifungal agents with acceptable toxicity profiles led first to the discovery of ketoconazole, the first azole-based oral treatment of systemic fungal infections, in the early 1980s. Later, triazoles fluconazole and itraconazole, with a broader spectrum of antifungal activity and improved safety profile were developed. In order to overcome limitations such as sub-optimal spectra of activity, drug-drug interactions, toxicity, development of resistance and unfavorable pharmacokinetics, analogues were developed. Second-generation triazoles, including voriconazole, posaconazole and ravuconazole, are more potent and more active against resistant pathogens.

For wood preservation, other azoles such as propiconazole, tebuconazole and cyproconazole, are used as antifungal agents in several wood products or structures, with or without the addition of copper-containing compounds. Such azoles possess a good activity in solvents and water-based formulations, and are effective against wood-destroying, rot fungi.

References

Maertens, J. A.. (2004-03-01). "History of the development of azole derivatives". Clinical Microbiology and Infection.
(2021-09-07). "Azole Use in Agriculture, Horticulture, and Wood Preservation -Is It Indispensable?". Frontiers.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::