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Amphiphilic Dipyrrinones

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Summary.

Replacing the typical lactam β-alkyl substituents of xanthobilirubinic acid and kryptopyrromethenone, two bilirubin analogs long used as model compounds in studies of its photochemistry and metabolism, leads to increased amphiphilicity. Synthesized by base-catalyzed condensation of 3,4-dimethoxypyrrolin-2-one with the appropriate pyrrole α-aldehyde, the 2,3-dimethoxyl analogs of xanthobilirubinic acid and kryptopyrromethenone are yellow-colored dipyrrinones that form intermolecular hydrogen-bonded dimers in the solid, as determined by X-ray crystallography, and in CHCl3, as revealed by 1H NMR and vapor pressure osmometry. These two new dipyrrinones are approximately ten times more soluble in water than their parent dipyrrinones.

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Authors and Affiliations

  1. Department of Chemistry, University of Nevada, Reno, Nevada, USA

    Sanjeev K. Dey & David A. Lightner

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  1. Sanjeev K. Dey
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  2. David A. Lightner
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Correspondence to David A. Lightner.

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Dey, S., Lightner, D. Amphiphilic Dipyrrinones. Monatsh. Chem. 138, 687–697 (2007). https://doi.org/10.1007/s00706-007-0652-z

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