Determination of the Stereochemistry of Substituted 5-Methylenehydantoins and Thiohydantoins by 13C NMR and Homonuclear NOE Experiments |
| |
| Authors: | Patrick Fresneau François Thomasson Jean-Marc Morand Max Cussac |
| |
| Institution: | 1. Laboratoire de Chimie Thérapeutique , Groupe de Pharmacochimie Moléculaire;2. Laboratoire de Chimie Pharmacie URA CNRS n°1287, UFR de Pharmacie , Université Joseph Fourier de Grenoble I , 38706, La Tronche Cédex, France |
| |
| Abstract: | Basically the aim of this work is to define the accurate configuration of the exocyclic double bond of substituted 5-methylenehydantoins and thiohydantoins which have been conceived as potential Aldose Reductase inhibitors. A previsional survey based upon the chemical shifts analysis from 1H and decoupled 13C NMR spectra discloses, for a part of the family of compounds, the assignment of the Zconfiguration for unsubstituted (2,3) and N-3 substituted (6,7,9) derivatives, and the E-configuration for the N-1 substituted (8,11) ones. The qualitative study with Homonuclear NOE (8,11) and the coupling constant measuring 3 JC4-C=C-H6 from coupled 13C NMR (1–11), lead to the assignment of the accurate configuration of the whole family's compounds in agreement with the previsional study. |
| |
| Keywords: | Methylenehydantoins methylenethiohydantoins 1H NMR spectra 13C NMR spectra Homonuclear NOE C-H coupling constants |
|
|
