717110-11-7Relevant academic research and scientific papers
Synthesis, molecular modeling, and biological studies of novel piperidine-based analogues of cocaine: Evidence of unfavorable interactions proximal to the 3α-position of the piperidine ring
Petukhov, Pavel A.,Zhang, Jianrong,Wang, Cheng Z.,Ye, Yan Ping,Johnson, Kenneth M.,Kozikowski, Alan P.
, p. 3009 - 3018 (2007/10/03)
A qualitative model for the binding pocket proximal to the 3α-substituent of the piperidine-based monoamine transporter ligands was proposed and tested. Based on this model, a new series of druglike 3α-modified piperidine-based analogues of cocaine were d
SAR studies of piperidine-based analogues of cocaine. Part 3: Oxadiazoles
Petukhov, Pavel A.,Zhang, Mei,Johnson, Kenneth J.,Tella, Srihari R.,Kozikowski, Alan P.
, p. 2079 - 2083 (2007/10/03)
The synthesis of novel 4β-aryl-1-methyl-3α-(3-substituted-1,2,4-oxadiazol-5-yl) piperidines, bioisosteres of ester (+)-1, is described. The synthesized oxadiazoles were evaluated for their affinity to the DAT and their ability to inhibit monoamine reuptake at the DAT, NET, and 5HTT. The results show that affinity to the DAT and ability to inhibit the reuptake at the DAT, NET, and 5HTT is a function of the size of the substituent in the oxadiazole ring. (+)-(3R,4S)-4β-(4-Chlorophenyl)-1-methyl-3α-(3-methyl-1,2,4- oxadiazol-5-yl)piperidine [(+)-2a], which is structurally and pharmacologically most similar to the ester (+)-1 in this series, showed at least a 2-fold longer duration of action when compared to ester (+)-1.
Synthesis and biological evaluation of 1-azabicyclo-[3.2.1]octanes: New dopamine transporter inhibitors
Tamiz, Amir P.,Smith, Miles P.,Enyedy, Istvan,Flippen-Anderson, Judith,Zhang, Mei,Johnson, Kenneth M.,Kozikowski, Alan P.
, p. 1681 - 1686 (2007/10/03)
The synthesis and biological activity of a series of 6-substituted 1-azabicyclo[3.2.1]octanes are described. 1-Azabicyclo[3.2.1]octanes represent a new class of compounds that exhibit monoamine transporter inhibitory activity highly dependent on the overall topology and the absolute stereochemistry of the molecule. (C) 2000 Elsevier Science Ltd. All rights reserved.
