Molecular rearrangement of 5-(a-hydroxy-alkanoylamino)-2,4,6-triiodo-isophthalic acid amides.
Iomeprol, a new nonionic contrast agent, undergoes in alkaline solution a Smiles-type intramolecular rearrangement to give 5-methylaminocarbonylmethoxy-2,4,6-triiodoisophthalic acid-bis-(2,3-dihydroxypropylamide). The rearranged product was isolated and its structure confirmed by spectra and by synthesis. The reaction is reversible and could be extended to some structurally related compounds.
Felder
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Bracco Industria Chimica Spa, Milan, Italy.
Gallotti
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A
Favilla
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A
D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D003287:Contrast Media; D007479:Iopamidol / Q000031:analogs & derivatives*; D013329:Structure-Activity Relationship
D003287:Contrast Media; C057937:iomeprol; D007479:Iopamidol