Synthesis of novel 3-substituted. beta.-carbolines as benzodiazepine receptor ligands: probing the benzodiazepine receptor pharmacophore

…, ML Trudell, PW Codding, P Skolnick…

Index: Allen; Hagen; Trudell; Codding; Skolnick; Cook Journal of Medicinal Chemistry, 1988 , vol. 31, # 9 p. 1854 - 1861

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Citation Number: 91

Abstract

The 3-substituted P-carbolines 2-4 and 5-7 were prepared from 3-amino-@-carboline (8) in one step via diazotization, followed by reaction with the appropriate nucleophile in order to determine their binding affinity for benzodiazepine receptors (BzR). All three of the 3-alkoxy- P-carbolines 2 (ICw= 124 nM), 3 (ICso= 24 nM), and 4 (ICso= 11 nM) have high affinities for BzR. The@-carbolines ubstituted with electron-withdrawing groups including 5 (Cl; ICw= ...