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Azole

Class of heterocyclic compounds

Azole
Summary

Class of heterocyclic compounds

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.

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

;Nitrogen only Imidazol.svg|Imidazole Pyrazol.svg|Pyrazole 1,2,3-Triazole structure.svg|1,2,3-Triazole 1,2,4-Triazole structure.svg|1,2,4-Triazole 1H-Tetrazole structure.svg|Tetrazole Pentazol.svg|Pentazole

;N,O compounds Oxazol.svg|Oxazole Isoxazol.svg|Isoxazole 1,2,3-oxadiazole.svg|1,2,3-oxadiazole (unstable) 1,2,4-oxadiazole.svg|Oxadiazole (1,2,4-Oxadiazole) 1,2,5-oxadiazole.svg|Furazan (1,2,5-oxadiazole) 1,3,4-oxadiazole.svg |1,3,4-Oxadiazole

;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

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

References

  1. Maertens, J. A.. (2004-03-01). "History of the development of azole derivatives". Clinical Microbiology and Infection.
  2. (2021-09-07). "Azole Use in Agriculture, Horticulture, and Wood Preservation -Is It Indispensable?". Frontiers.
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.

azoles functional-groups
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