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Crystal structures of baclofen analogs: 3-thienyl- and 3-furylaminobutyric acids

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Abstract

X-ray crystal structures of 4-amino-3-(2-thienyl) butyric acid (compound1), 4-amino-3-(4-bromo-2-thienyl) butyric acid (compound2), and 4-amino-3-(5-methyl-2-furyl) butyric acid (compound3) are reported. Space groups and unit/cell parameters are: compound1, monoclinic,P21 c,a=13.288(3),b=5.231(1),c=12.388(2)Å,β=92.3(1)°; compound2, monoclinic,P21/c,a=12.610(7),b=5.156(1),c=15.814(8)Å,β=101.8(1)°; compound3, orthorhombic, Pccn,a=11.461(1),b=25.284(2),c=6.977(1)Å. FinalR indices are: compound1, 0.057; compound2, 0.069; compound3, 0.060. Conformations of their γ-aminobutyric chains are compared with the one of γ-amino-β-(p-chlorophenyl)-butyric acid (baclofen, compound4). Two different types of conformations are observed, i.e., conformations (i) with folding (compound3) or (ii) without folding (compounds1,2, and4) of the ammonium group toward the heteroaromatic or aromatic ring. However, distances between ionized groups are constant.

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Authors and Affiliations

  1. Laboratoire de Chimie Moléculaire Structurale, Facultés Universitaires Notre-Dame de la Paix, 61 rue de Bruxelles, B-5000, Namur, Belgium

    Bernard Pirard, Guy Evrard, Bernadette Norberg, Daniel P. Vercauteren & François Durant

  2. Laboratoire de Pharmacie Chimique, U.F.R. de Pharmacie, 3 rue du Professeur Laguesse, 59006, Lille Cédex, France

    Pascal Berthelot, Claude Vaccher & Michel Debaert

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  1. Bernard Pirard
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  2. Guy Evrard
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  3. Bernadette Norberg
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  4. Pascal Berthelot
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  5. Claude Vaccher
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  6. Michel Debaert
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  7. Daniel P. Vercauteren
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  8. François Durant
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Pirard, B., Evrard, G., Norberg, B. et al. Crystal structures of baclofen analogs: 3-thienyl- and 3-furylaminobutyric acids. Journal of Crystallographic and Spectroscopic Research 23, 843–848 (1993). https://doi.org/10.1007/BF01195730

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  • DOI: https://doi.org/10.1007/BF01195730

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