Structural, conformational and pharmacological study of some amides derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9β-amine as potential analgesics

被引:3
作者
Iriepa, I
Gil-Alberdi, B
Gálvez, E
Herranz, MJ
Bellanato, J
Carmona, P
Orjales, A
Berisa, A
Labeaga, L
机构
[1] Univ Alcala de Henares, Dept Quim Organ, Madrid, Spain
[2] CSIC, Inst Estructura Mat, E-28006 Madrid, Spain
[3] Labs FAES SA, Bilbao, Spain
关键词
3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9 beta-amine; vibrational spectroscopy; NMR spectroscopy;
D O I
10.1016/S0022-2860(98)00945-4
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A series of amides derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9 beta-amine were synthesized and studied by IR, Raman,H-1 and C-13 NMR spectroscopy The compounds studied displayed in CDCl3 a preferred flattened chair-chair conformation. IR (at room and variable temperature) and H-1 and C-13 NMR data showed the presence of an intramolecular NH ... N-heterocyclic hydrogen bond in the pirazine derivative (TV). Pharmacological assays on mice were drawn to evaluate drug-induced behavioral alteration peripheral or central acute toxicity and analgesic activity. (C) 1999 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:425 / 430
页数:6
相关论文
共 16 条
[1]   STRUCTURAL AND CONFORMATIONAL STUDY OF 3-PHENETHYL-3-AZABICYCLO[3.2.1]OCTAN-8-BETA-OL [J].
ARIAS, MS ;
GALVEZ, E ;
ARDID, I ;
BELLANATO, J ;
GARCIARAMOS, JV ;
FLORENCIO, F ;
GARCIABLANCO, S .
JOURNAL OF MOLECULAR STRUCTURE, 1987, 161 :151-164
[2]   STRUCTURAL STUDY OF ETHYL 3-METHYL-9-OXO-3-AZABICYCLO[3.3.1]NONANE-1-CARBOXYLATE BY 2-DIMENSIONAL NMR-SPECTROSCOPY [J].
ARIASPEREZ, MS ;
ALEJO, A ;
GALVEZ, E ;
PEREZ, SM ;
SANTOS, MJ .
JOURNAL OF MOLECULAR STRUCTURE, 1995, 349 :169-174
[3]   SYNTHESIS, AND STRUCTURAL, CONFORMATIONAL AND PHARMACOLOGICAL STUDIES OF NEW FENTANYL DERIVATIVES OF THE NORGRANATANE SYSTEM [J].
FERNANDEZ, MJ ;
HUERTAS, RM ;
GALVEZ, E ;
ORJALES, A ;
BERISA, A ;
LABEAGA, L ;
GAGO, F ;
FONSECA, I ;
SANZAPARICIO, J ;
CANO, FH ;
ALBERT, A ;
FAYOS, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :687-695
[4]   SYNTHESIS AND STRUCTURAL STUDY OF ANIMALS DERIVED FROM 8-AMINOQUINOLINE AND 1-AMINONAPHTALENE [J].
GALVEZ, E ;
IRIEPA, I ;
LORENTE, A ;
MOHEDANO, JM ;
FLORENCIO, F ;
GARCIABLANCO, S .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (04) :687-692
[5]   STRUCTURAL AND SPECTROSCOPIC STUDY OF CONDENSED PIPERIDINE BICYCLANOLS.3-PHENETHYL-3-AZABICYCLO[3.2.1]OCTAN-8-ALPHA-OL [J].
GALVEZ, E ;
ARIAS, MS ;
ARDID, I ;
FLORENCIO, F ;
SANZAPARICIO, J ;
BELLANATO, J ;
GARCIARAMOS, JV .
JOURNAL OF MOLECULAR STRUCTURE, 1989, 196 :307-316
[6]   STRUCTURAL AND CONFORMATIONAL STUDY OF DIAZABICYCLANONES AND DIAZABICYCLANOLS [J].
GALVEZ, E ;
ARIAS, MS ;
BELLANATO, J ;
GARCIARAMOS, JV ;
FLORENCIO, F ;
SMITHVERDIER, P ;
GARCIABLANCO, S .
JOURNAL OF MOLECULAR STRUCTURE, 1985, 127 (3-4) :185-201
[7]  
GILALBERDI B, 1996, THESIS U ALCALA HENA
[8]   THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].
HAASNOOT, CAG ;
DELEEUW, FAAM ;
ALTONA, C .
TETRAHEDRON, 1980, 36 (19) :2783-2792
[9]  
HASSNER A, 1978, TETRAHEDRON LETT, P4475
[10]   STRUCTURAL, CONFORMATIONAL AND PHARMACOLOGICAL STUDY OF SOME ESTERS DERIVED FROM 3-METHYL-2,4-DIPBENYL-3-AZABICYCLO[3.3.1]NONAN-9-BETA-OL [J].
IRIEPA, I ;
GILALBERDI, B ;
GALVEZ, E ;
SANZAPARICIO, J ;
FONSECA, I ;
ORJALES, A ;
BERISA, A .
JOURNAL OF MOLECULAR STRUCTURE, 1995, 351 :119-125