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Chemical compound
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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.[5][6][7][8][9]
When fused to a pyrimidine ring, it forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature.[10]
The name "imidazole" was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935).[11]
^"Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 140. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^Walba, H.; Isensee, R. W. (1961). "Acidity constants of some arylimidazoles and their cations". J. Org. Chem. 26 (8): 2789–2791. doi:10.1021/jo01066a039.
^"Imidazole". molekula.com. Molekula Group. Archived from the original on 2018-10-19. Retrieved 2018-10-19.
^"Imidazole". pubchem.ncbi.nlm.nih.gov. Archived from the original on 10 May 2023. Retrieved 17 February 2024.
^Karitzky, A. R.; Rees, C.W.R.; Scriven, E.F.V. (1984). Comprehensive Heterocyclic Chemistry. Vol. 5. pp. 469–498. ISBN 978-0-08-042072-1.
^Grimmett, M. Ross (1997). Imidazole and Benzimidazole Synthesis. Academic Press. ISBN 978-0-08-053445-9.
^Brown, E. G. (1998). Ring Nitrogen and Key Biomolecules. Kluwer Academic Press. ISBN 978-94-011-4906-8.
^Pozharskii, A. F.; et al. (1997). Heterocycles in Life and Society. John Wiley & Sons. ISBN 978-0-471-96033-1.
^Gilchrist, T. L. (1985). Heterocyclic Chemistry. Bath Press. ISBN 978-0-582-01421-3.
^Rosemeyer, H. (2004). "The Chemodiversity of Purine as a Constituent of Natural Products". Chemistry & Biodiversity. 1 (3): 361–401. doi:10.1002/cbdv.200490033. PMID 17191854. S2CID 12416667.
^Hantzsch, A. and Weber, J. H. (1887) "Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe)" Archived 2020-05-30 at the Wayback Machine (On compounds of thiazole (pyridines of the thiophene series), Berichte der deutschen chemischen Gesellschaft, 20 : 3118–3132, see p. 3119. See also: Hantzsch, A. (1888) "Allegemeine Bemerkungen über Azole" Archived 2020-05-30 at the Wayback Machine (General observations about azoles), Annalen der Chemie, 249 : 1–6. Hantzsch proposed a reform of the nomenclature of azole compounds, including a proposal to call the heterocyclic ring C3H3(NH)N "imidazole" ; see pp. 2 and 4.
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...
(protonated form) of the imidazole side chain in histidine has a pKa of approximately 6.0. Thus, below a pH of 6, the imidazole ring is mostly protonated...
Imidazole alkaloids are a group of alkaloids whose basic structure contains the imidazole ring system. In nature, imidazole alkaloids are found both as...
ring containing two or three nitrogen atoms. The imidazole antifungals contain a 1,3-diazole (imidazole) ring (two nitrogen atoms), whereas the triazole...
compound may be viewed as fused rings of the aromatic compounds benzene and imidazole. It is a white solid that appears in form of tabular crystals. Benzimidazole...
aromatic organic compound that consists of two rings (pyrimidine and imidazole) fused together. It is water-soluble. Purine also gives its name to the...
A transition metal imidazole complex is a coordination complex that has one or more imidazole ligands. Complexes of imidazole itself are of little practical...
Nitroimidazoles are the group of organic compounds consisting of an imidazole ring with at least one nitro group substituent. The term also refers to...
which captures carbon dioxide to give a zinc bicarbonate: [(imidazole)3ZnOH]+ + CO2 ⇌ [(imidazole)3ZnOCO2H]+ In reinforced concrete, the chemical reaction...
In a variation of the Ullmann reaction, β-bromostyrene is reacted with imidazole in an ionic liquid such as 1-butyl-3-methylimidazolium tetrafluoroborate...
this conversion, the imidazole serves both as the nucleophile and the base. An alternative precursor 1-(trimethylsilyl)imidazole requires more preparative...
The enzyme Phosphoribosylaminoimidazole carboxylase, or AIR carboxylase (EC 4.1.1.21) is involved in nucleotide biosynthesis and in particular in purine...
allow them to engage pathogens in the infected tissues. It consists of an imidazole ring attached to an ethylamine chain; under physiological conditions,...
part of a double bond, and then proceeds towards the other heteroatom. Imidazole and other five-membered aromatic heterocyclic systems with two nitrogens...
a phosphoryl mono-ester is covalently bound to a nitrogen atom in an imidazole ring. They are a type of phosphoramidate. These phosphorus (V) compounds...
(gene)) is an enzyme with systematic name 5-amino-1-(5-phospho-D-ribosyl)imidazole formate-lyase (decarboxylating, 4-amino-2-methyl-5-phosphomethylpyrimidine-forming)...
in pregnancy is believed to be safe for the baby. Miconazole is in the imidazole family of medications. It works by decreasing the ability of fungi to...