Imidazolone

Imidazolinones or imidazolones are a family of heterocyclic compounds, the parents of which have the formula OC(NH)2(CH)2. Two isomers are possible, depending on the location of the carbonyl (CO) group. The NH groups are nonadjacent. A common route to imidazol-2-ones involves condensation of ureas and acyloins.[2] Some are of interest in the pharmaceuticals.[3] 4-Imidazolones arise from the condensation of amidines with 1,2-dicarbonyls such as glyoxal.[1]

4-imidazolones are advanced glycation endproducts (AGEs), a class of modified proteins that are biomarkers for diabetes. In this drawing the imidazolone is the C3N2 ring in red and black.[1]

References
  1. Bellier, Justine; Nokin, Marie-Julie; Lardé, Eva; Karoyan, Philippe; Peulen, Olivier; Castronovo, Vincent; Bellahcène, Akeila (2019). "Methylglyoxal, a Potent Inducer of AGEs, Connects between Diabetes and Cancer". Diabetes Research and Clinical Practice. 148: 200-211. doi:10.1016/j.diabres.2019.01.002.
  2. Corson, B. B.; Freeborn, Emeline (1932). "4,5-Diphenylglyoxalone". Org. Synth. 12: 34. doi:10.15227/orgsyn.012.0034.
  3. Antonova, Maria M.; Baranov, Vladimir V.; Kravchenko, Angelina N. (2015). "Methods for the synthesis of 1-substituted 1H-imidazol-2(3H)-ones". Chemistry of Heterocyclic Compounds. 51: 395–420. doi:10.1007/s10593-015-1716-3.
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