ISSN:
0749-1581
Keywords:
Tianeptine
;
Antidepressant drug
;
Conformation
;
1H NMR
;
13C NMR
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The conformational behaviour of 7-[(3-chloro-6,11-dihydro-6-methyldibenzo[c, f][1,2]thiazepin-11-yl)amino] heptanoic acid 5,5 dioxide (tianeptine), a new antidepressant drug, was studied by means of 1H and 13C NMR. The ring skeleton exhibits two distinct conformations at low temperature. The conformational exchange is still restricted at room temperature, particularly in the solvents D2O and CDCl3, where significant aggregation of the molecules occurs. The side-chain seems to adopt a preferential conformation where it is bent over the unsubstituted aromatic ring. This conformational preference in the biologically active structure might be related to the observed loss of activity when substituents are introduced on the aromatic rings.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260301210
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