Abstract
The crystal structure of the title compound (1 ) has been solved by direct methods from single crystal X-ray diffraction. Monoclinic, space group P2 1/c with a = 9.277(1), b = 9.977(2), c = 18.557(2) Å, β = 98.44(1)°; Z = 4. The final R-factor is 0.03 for 2923 observed reflections. The inactive title compound (for the dopaminergic D2 receptor) containing a benzosulphonamide function is compared with a very potent benzamide analogue: tropapride (2). The molecular conformation of the title compound obtained by optimal superimposition (flexible fitting) of the proposed pharmacophoric elements with those of tropapride corresponds to a significantly less stable conformation as shown by ab initio LCAO-MO-SCF calculations. In fact, the electron-attracting mesomeric effect of the sulphone group excludes the formation of a strong intramolecular hydrogen bond which would stabilize the tropapride-like conformation of the lateral chain.
Original language | English |
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Pages (from-to) | 407-412 |
Number of pages | 6 |
Journal | Journal of the Chemical Society. Perkin Transactions 2 |
Issue number | 5 |
Publication status | Published - 1989 |