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(m.n)-Homorubins: syntheses and structures

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Abstract

Five new homorubin analogs of bilirubin with their two dipyrrinone components conjoined to (CH2)2, (CH2)3, and (CH2)4 units were synthesized with propionic acid chains shortened to acetic and elongated to butyric, and examined by spectroscopy and molecular mechanics computations for an ability to form conformation-determining hydrogen bonds. With m designating the number of conjoining CH2 units and n indicating the number of CH2 units of the alkanoic acid chains of (m.n)-homorubins, (2.1)-, (3.2)-, (4.2)-, and (4.3)-homorubins were prepared and compared with previously synthesized (2.2) and (2.3), which adopt intramolecularly hydrogen-bonded conformations in CHCl3.

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Acknowledgments

We thank the late Prof. A. F. McDonagh (Univ. California, San Francisco) for the metabolism studies and the National Institutes of Health for partial support.

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Authors and Affiliations

  1. Apex International, Eden Prairie, MN, 55344, USA

    William P. Pfeiffer

  2. Department of Chemistry, University of Nevada, Reno, NV, 89557-0216, USA

    David A. Lightner

Authors
  1. William P. Pfeiffer
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  2. David A. Lightner
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Correspondence to David A. Lightner.

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Pfeiffer, W.P., Lightner, D.A. (m.n)-Homorubins: syntheses and structures. Monatsh Chem 145, 1777–1801 (2014). https://doi.org/10.1007/s00706-014-1288-4

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  • DOI: https://doi.org/10.1007/s00706-014-1288-4

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