Imidazolone

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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. HydroimidazoloneAGE.png
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.

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]

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7
H
5
NS
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6
N
10
H
6
; specifically, 2,5,8-triamino-heptazine or 2,5,8-triamino-tri-s-triazine, whose molecule can be described as that of heptazine with the three hydrogen atoms replaced by amino groups. It is a white crystalline solid.

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1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids. It is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine.

<span class="mw-page-title-main">Tetraphenylporphyrin</span> Chemical compound

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Imidazolidinones or imidazolinones are a class of 5-membered ring heterocycles structurally related to imidazole. Imidazolidinones feature a saturated C3N2 backbones, except for the presence of a urea or amide functional group in the 2 or 4 positions.

References

  1. 1 2 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.