Molecular structure analysis of benzamide neuroleptics. Part 13. A tropapride sulphonamidic analogue C15H22N 3O3SCI

Sonia Collin, Daniel P. Vercauteren, Guy Evrard, François Durant

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Pages (from-to)407-412
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number5
Publication statusPublished - 1989

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