Are you an EPFL student looking for a semester project?
Work with us on data science and visualisation projects, and deploy your project as an app on top of Graph Search.
Concept
Azole
Summary
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. 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.
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]]
Tetrazole Structural Formulae.png|[[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]
1,2,5-oxadiazole.svg|[Furazan]
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]
1,2,4-thiadiazole-2D-skeletal.png |1,2,4-thiadiazole
1,2,5-thiadiazole-2D-skeletal.png |1,2,5-thiadiazole
1,3,4-thiadiazole-2D-skeletal.png |1,3,4-thiadiazole
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.
Official source
About this result
This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.
Related lectures (3)
The Chemistry of Poisonous Frogs: Alkynes and Aromatic Compounds
Explores the chemistry of poisonous frogs and alkynes, highlighting their unique synthesis abilities and medicinal applications.
Microbial Control: Methods and Applications
Explores methods of microbial control, including heat, radiation, filtration, pasteurization, and antibiotics, as well as the challenges of antimicrobial resistance.
Surface Curvature and Assimilation
Explores surface curvature, curve assimilation, soap bubbles, capillarity, fluid mechanics, and types of flow.
Related publications (17)
Single-Cell Optical Nanomotion of Candida albicans in Microwells for Rapid Antifungal Susceptibility Testing
Sandor Kasas, María Inés Villalba
Candida albicans is an emerging multidrug-resistant opportunistic pathogen representing an important source of invasive disease in humans and generating high healthcare costs worldwide. The development of a rapid and simple antifungal susceptibility test ( ...
MDPI2023Related people (3)
Related concepts (6)
Imidazole
Imidazole (ImH) is an organic compound with the formula C3N2H4. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.
Triazole
A triazole is a heterocyclic compound featuring a five-membered ring of two carbon atoms and three nitrogen atoms with molecular formula C2H3N3. Triazoles exhibit substantial isomerism, depending on the positioning of the nitrogen atoms within the ring. Many triazoles are versatile, biologically active compounds commonly used as fungicides and plant retardants. However, triazoles are also useful in bioorthogonal chemistry, because the large number of nitrogen atoms causes triazoles to react similar to azides.
Fluconazole
Fluconazole is an antifungal medication used for a number of fungal infections. This includes candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and pityriasis versicolor. It is also used to prevent candidiasis in those who are at high risk such as following organ transplantation, low birth weight babies, and those with low blood neutrophil counts. It is given either by mouth or by injection into a vein. Common side effects include vomiting, diarrhea, rash, and increased liver enzymes.