Structural studies of five novel bile acid-4-aminopyridine conjugates |
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Authors: | Kari V Ahonen Manu K Lahtinen Miika S Löfman Anniina M Kiesilä Arto M Valkonen Elina I Sievänen Nonappa Erkki T Kolehmainen |
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Affiliation: | 1. Department of Chemistry, Laboratory of Organic Chemistry, P.O. Box 35, FIN-40014 University of Jyväskylä , Finland;2. Department of Chemistry, Laboratory of Inorganic and Analytical Chemistry, P.O. Box 35, FIN-40014 University of Jyväskylä, Finland |
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Abstract: | Synthesis and solid-state structural characterization of five bile acid amides of 4-aminopyridine (4-AP) are reported. Systematic crystallization experiments revealed a number of structural modifications and/or solvate/hydrate systems for these conjugates. Particularly, cholic acid conjugate exhibited five distinct structure modifications, including one anhydrous form, mono- and dihydrates, as well as ethanol and 2-butanol solvates. The obtained crystal forms were examined extensively with various analytical methods, including solid-state NMR, Raman, and IR spectroscopies, powder and single crystal X-ray diffraction methods, thermogravimetry, and differential scanning calorimetry. After releasing their crystal solvent molecules, the resulted non-solvated structure forms showed 50-75°C higher melting points than corresponding bile acids, and thermal degradation occurred for all conjugates at about 300-330°C. Moreover, the single crystal X-ray structure of the ursodeoxycholic acid-4-aminopyridine conjugate is reported. |
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