Journal of Pharmaceutical Sciences p. 101 - 106 (1995)
Update date:2022-08-04
Topics:
Whelan
Iriepa
Galvez
Orjales
Berisa
Labeaga
Garcia
Uceda
Sanz-Aparicio
Fonseca
A series of tropane-3-spiro-4'(5')-imidazolines was synthesized and studied by 1H and 13C NMR spectroscopy, and the crystal structure of 2'- (1H-indol-3-yl)tropane-3-spiro-4'(5')-imidazoline hydrochloride 5(6)f was determined by X-ray diffraction. In CD3OD solution, compounds 5(6)a-f display the same preferred conformation. The pyrrolidine and piperidine rings adopt an envelope conformation flattened at N8 and a distorted chair conformation puckered at N8 and flattened at C3, respectively, with the N- substituent in the equatorial position with respect to the piperidine ring. This conformation is similar to that observed for compound 5(6)f in the solid state. From binding studies on the compounds synthesized, compound 5(6)d demonstrated the ability to efficiently displace the binding of [3H]GR65630 to bovine brain area postrema membranes to an extent comparable to MDL 72222. In the von Bezold-Jarisch reflex, compound 5(6)d was equipotent with metoclopramide. It is, therefore, likely that the imidazoline ring may provide a useful bioisosteric replacement for the carbonyl group in 5-HT3 antagonists.
View Morewebsite:http://www.simagchem.com
Contact:+86-592-2680277
Address:21/F Hualong Office Building,No.6 Hubin East Road, Xiamen,China
Contact:+31-24-3886056
Address:Binderskampweg 29 Unit 36
Changzhou Ruiping Chemical Co., Ltd
website:http://www.wishchem.com
Contact:+86-519-82324280
Address:No.288-1 Huacheng Road, Jintan
Nanjing Qirui Material Co., Ltd.
Contact:+86-25-52320053
Address:F4-5, #17 Building, Chuang Yi Yuan, No.6 Guanghua East Street, Nanjing, 210007 P.R.China
Contact:86-10-62664360
Address:Building 10,No.18 AnNingZhuang East Road, GuangHua Pioneer Park,HaiDian District, BeiJing China
Doi:10.1016/j.tetlet.2009.09.057
(2009)Doi:10.1039/b911489k
(2009)Doi:10.1016/j.ejmech.2009.06.016
(2009)Doi:10.1002/chem.200901126
(2009)Doi:10.1039/c7ra02217d
(2017)Doi:10.1007/BF00961962
(1988)