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A series of amides derived from 3,7-dimethyl-3,7-diazabicyclo [3.3.1] nonan-9-amine have been synthesized and examined by 1 H and 13 C NMR spectroscopy and the crystal structure of 9-(2,4,6-trichlorobenzamido)-3,7-dimethyl-3,7-diazabicyclo[3.3.1] nonane hydrochloride ( 4a ·HCl) has been determined by X-ray diffraction. These compounds adopt an almost perfect chair-chair conformation with the NCH 3 groups in equatorial position. This conformation is nearly the same as that observed for compound 4a in the solid state. From binding studies of compounds 4a–c , compound 4b demonstrated the ability to efficiently displace [ 3 H]GR65630 bound to bovine brain area postrema membranes to an extent comparable to MDL 72222. In the von Bezold-Jarish reflex, compound 4b showed significant results at a dose of 25 mg Kg −1 . It is shown for the first time that a series of compounds with a bispidine skeleton linked through an amide moiety to several aromatic rings, shows 5-HT 3 antagonistic profiles. |
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