4-Piperidines and 3-pyrrolidines as dual serotonin and noradrenaline reuptake inhibitors: Design, synthesis and structure-activity relationships

被引：16

作者：

Fish, Paul V. ^{[1
]}

Andrews, Mark D. ^{[1
]}

Fray, M. Jonathan ^{[1
]}

Stobie, Alan ^{[1
]}

Wakenhut, Florian ^{[1
]}

Whitlock, Gavin A. ^{[1
]}

机构：

[1] Pfizer Global Res & Dev, Sandwich Labs, Discovery Chem, Sandwich CT13 9NJ, Kent, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 10期

关键词：

Dual SNRI; Selective SRI; Selective NRI; Triple SNDRI; 4-Piperidine; 3-Piperidine; 3-Pyrrolidine; Monoamine reuptake inhibitor; DERIVATIVES; NOREPINEPHRINE; DRUGS;

D O I：

10.1016/j.bmcl.2009.03.090

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Single enantiomer [(aryloxy)(pyridinyl) methyl] piperidine and pyrrolidine derivatives 5-9 are inhibitors of monoamine reuptake. Structure-activity relationships established that monoamine reuptake inhibition are functions of amine, pyridine isomer, aryloxy ring substitution and stereochemistry. Consequently, selective NRIs, selective SRIs, dual SNRIs and triple SNDRIs were all identified. Dual SNRIs 51-a and 9c were evaluated in additional pharmacology and pharmacokinetic studies as representative examples from this series. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2829 / 2834

页数：6

共 50 条

[31] Synthesis, Structure-Activity Relationships, and In Vivo Evaluation of Novel Tetrahydropyran-Based Thiodisaccharide Mimics as Galectin-3 Inhibitors
Xu, Li
Hartz, Richard A.
Beno, Brett R.
Ghosh, Kaushik
Shukla, Jinal K.
Kumar, Amit
Patel, Dipal
Kalidindi, Narasimharaju
Lemos, Nadine
Gautam, Shashyendra Singh
Kumar, Anoop
Ellsworth, Bruce A.
Shah, Devang
Sale, Harinath
Cheng, Dong
Regueiro-Ren, Alicia
JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (10) : 6634 - 6655
[32] Structural Design, Synthesis and Structure-Activity Relationships of Thiazolidinones with Enhanced Anti-Trypanosoma cruzi Activity
Magalhaes Moreira, Diogo Rodrigo
Lima Leite, Ana Cristina
Oliveira Cardoso, Marcos Verissimo
Srivastava, Rajendra Mohan
Hernandes, Marcelo Zaldini
Rabello, Marcelo Montenegro
da Cruz, Luana Faria
Ferreira, Rafaela Salgado
de Simone, Carlos Alberto
Meira, Cassio Santana
Guimaraes, Elisalva Teixeira
da Silva, Aline Caroline
dos Santos, Thiago Andre Ramos
Alves Pereira, Valeria Rego
Pereira Soares, Milena Botelho
CHEMMEDCHEM, 2014, 9 (01) : 177 - 188
[33] Structure-activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors
Im, Isak
Lee, Eui Seung
Choi, Soo Jeong
Lee, Ju-Yeon
Kim, Yong-Chul
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (13) : 3632 - 3636
[34] Structure-activity relationships of the 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ol series of monoamine reuptake inhibitors
Mahaney, Paige E.
Kim, Callain Y.
Coghlan, Richard D.
Cohn, Stephen T.
Heffernan, Gavin D.
Huselton, Christine A.
Terefenko, Eugene A.
Vu, An T.
Zhang, Puwen
Burroughs, Kevin D.
Cosmi, Scott A.
Bray, Jenifer A.
Johnston, Grace H.
Deecher, Darlene C.
Trybulski, Eugene J.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (19) : 5807 - 5810
[35] Combined 3D-quantitative structure-activity relationships and topomer technology-based molecular design of human 4-hydroxyphenylpyruvate dioxygenase inhibitors
Liu, Yong-Xuan
Gao, Shuang
Ye, Tong
Li, Jia-Zhong
Ye, Fei
Fu, Ying
FUTURE MEDICINAL CHEMISTRY, 2020, 12 (09) : 795 - 811
[36] Biphenyl Pyridazinone Derivatives as Inhaled PDE4 Inhibitors: Structural Biology and Structure-Activity Relationships
Gracia, Jordi
Antonia Buil, Maria
Castro, Jordi
Eichhorn, Peter
Ferrer, Manel
Gavalda, Amadeu
Hernandez, Begona
Segarra, Victor
Lehner, Martin D.
Moreno, Imma
Pages, Lluis
Roberts, Richard S.
Serrat, Jordi
Sevilla, Sara
Taltavull, Joan
Andres, Miriam
Cabedo, Judit
Vilella, Dolors
Calama, Elena
Carcasona, Carla
Miralpeix, Montserrat
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (23) : 10479 - 10497
[37] Phosphodiesterase inhibitors. Part 6: Design, synthesis, and structure-activity relationships of PDE4-inhibitory pyrazolo[1,5-a]pyridines with anti-inflammatory activity
Kojima, Akihiko
Takita, Satoshi
Sumiya, Tatsunobu
Ochiai, Koji
Iwase, Kazuhiko
Kishi, Tetsuya
Ohinata, Akira
Yageta, Yuichi
Yasue, Tokutaro
Kohno, Yasushi
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (19) : 5311 - 5316
[38] Structure-activity relationships of 2-arylquinazolin-4-ones as highly selective and potent inhibitors of the tankyrases
Nathubhai, Amit
Haikarainen, Teemu
Hayward, Penelope C.
Munoz-Descalzo, Silvia
Thompson, Andrew S.
Lloyd, Matthew D.
Lehtio, Lari
Threadgill, Michael D.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 118 : 316 - 327
[39] Design, Synthesis, and Structure-Activity Relationships of Thiazole Analogs as Anticholinesterase Agents for Alzheimer's Disease
Saglik, Begum Nurpelin
Osmaniye, Derya
Cevik, Ulviye Acar
Levent, Serkan
Cavusoglu, Betul Kaya
Ozkay, Yusuf
Kaplancikli, Zafer Asim
MOLECULES, 2020, 25 (18):
[40] Design, Synthesis, and Structure-Activity Relationship of N-Arylnaphthylamine Derivatives as Amyloid Aggregation Inhibitors
Di Santo, Roberto
Costi, Roberta
Crucitti, Giuliana Cuzzucoli
Pescatori, Luca
Rosi, Federica
Scipione, Luigi
Celona, Diana
Vertechy, Mario
Ghirardi, Orlando
Piovesan, Paola
Marzi, Mauro
Caccia, Silvio
Guiso, Giovanna
Giorgi, Fabrizio
Minetti, Patrizia
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (19) : 8538 - 8548

← 1 2 3 4 5 →