Design and Synthesis of 4-Heteroaryl 1,2,3,4-Tetrahydroisoquinolines as Triple Reuptake Inhibitors
Shuang Liu
1
,
Congxiang Zha
1
,
Kassoum Nacro
1
,
Min Hu
1
,
Wenge Cui
1
,
Yuh Lin Yang
1
,
Ulhas Bhatt
1
,
Aruna Sambandam
1
,
Matthew Isherwood
1
,
Larry Yet
1
,
Michael T Herr
1
,
Sarah Ebeltoft
1
,
Carla Hassler
1
,
Linda Fleming
1
,
Anthony D Pechulis
1
,
Anne Payen Fornicola
1
,
Nicholas Holman
1
,
Dennis Milanowski
1
,
Ian Cotterill
1
,
Vadim Mozhaev
1
,
Yuri Khmelnitsky
1
,
Peter R Guzzo
1
,
Bruce J. Sargent
1
,
Bruce F Molino
1
,
Richard Olson
2
,
H Dalton King
2
,
Snjezana Lelas
2
,
Yu Wen Li
2
,
Kim Johnson
2
,
Thaddeus Molski
2
,
Anitra Orie
2
,
Alicia Ng
2
,
Roy Haskell
2
,
Wendy Clarke
2
,
Robert Bertekap
2
,
Jonathan O'Connell
2
,
Nicholas Lodge
2
,
Michael Sinz
2
,
Stephen Adams
2
,
ROBERT ZACZEK
2
,
John E. Macor
2
1
AMRI, 26 Corporate Circle, Albany, New York 12212, United States
|
Publication type: Journal Article
Publication date: 2014-05-27
scimago Q1
wos Q2
SJR: 0.805
CiteScore: 5.8
Impact factor: 4.0
ISSN: 19485875
PubMed ID:
25050161
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A series of 4-bicyclic heteroaryl 1,2,3,4-tetrahydroisoquinoline inhibitors of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) was discovered. The synthesis and structure-activity relationship (SAR) of these triple reuptake inhibitors (TRIs) will be discussed. Compound 10i (AMR-2), a very potent inhibitor of SERT, NET, and DAT, showed efficacy in the rat forced-swim and mouse tail suspension models with minimum effective doses of 0.3 and 1 mg/kg (po), respectively. At efficacious doses in these assays, 10i exhibited substantial occupancy levels at the three transporters in both rat and mouse brain. The study of the metabolism of 10i revealed the formation of a significant active metabolite, compound 13.
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Total citations:
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Citations from 2024:
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Liu S. et al. Design and Synthesis of 4-Heteroaryl 1,2,3,4-Tetrahydroisoquinolines as Triple Reuptake Inhibitors // ACS Medicinal Chemistry Letters. 2014. Vol. 5. No. 7. pp. 760-765.
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Liu S., Zha C., Nacro K., Hu M., Cui W., Yang Y. L., Bhatt U., Sambandam A., Isherwood M., Yet L., Herr M. T., Ebeltoft S., Hassler C., Fleming L., Pechulis A. D., Payen Fornicola A., Holman N., Milanowski D., Cotterill I., Mozhaev V., Khmelnitsky Y., Guzzo P. R., Sargent B. J., Molino B. F., Olson R., Dalton King H., Lelas S., Li Yu. W., Johnson K., Molski T., Orie A., Ng A., Haskell R., Clarke W., Bertekap R., O'Connell J., Lodge N., Sinz M., Adams S., ZACZEK R., Macor J. E. Design and Synthesis of 4-Heteroaryl 1,2,3,4-Tetrahydroisoquinolines as Triple Reuptake Inhibitors // ACS Medicinal Chemistry Letters. 2014. Vol. 5. No. 7. pp. 760-765.
Cite this
RIS
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TY - JOUR
DO - 10.1021/ml500053b
UR - https://doi.org/10.1021/ml500053b
TI - Design and Synthesis of 4-Heteroaryl 1,2,3,4-Tetrahydroisoquinolines as Triple Reuptake Inhibitors
T2 - ACS Medicinal Chemistry Letters
AU - Liu, Shuang
AU - Zha, Congxiang
AU - Nacro, Kassoum
AU - Hu, Min
AU - Cui, Wenge
AU - Yang, Yuh Lin
AU - Bhatt, Ulhas
AU - Sambandam, Aruna
AU - Isherwood, Matthew
AU - Yet, Larry
AU - Herr, Michael T
AU - Ebeltoft, Sarah
AU - Hassler, Carla
AU - Fleming, Linda
AU - Pechulis, Anthony D
AU - Payen Fornicola, Anne
AU - Holman, Nicholas
AU - Milanowski, Dennis
AU - Cotterill, Ian
AU - Mozhaev, Vadim
AU - Khmelnitsky, Yuri
AU - Guzzo, Peter R
AU - Sargent, Bruce J.
AU - Molino, Bruce F
AU - Olson, Richard
AU - Dalton King, H
AU - Lelas, Snjezana
AU - Li, Yu Wen
AU - Johnson, Kim
AU - Molski, Thaddeus
AU - Orie, Anitra
AU - Ng, Alicia
AU - Haskell, Roy
AU - Clarke, Wendy
AU - Bertekap, Robert
AU - O'Connell, Jonathan
AU - Lodge, Nicholas
AU - Sinz, Michael
AU - Adams, Stephen
AU - ZACZEK, ROBERT
AU - Macor, John E.
PY - 2014
DA - 2014/05/27
PB - American Chemical Society (ACS)
SP - 760-765
IS - 7
VL - 5
PMID - 25050161
SN - 1948-5875
ER -
Cite this
BibTex (up to 50 authors)
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@article{2014_Liu,
author = {Shuang Liu and Congxiang Zha and Kassoum Nacro and Min Hu and Wenge Cui and Yuh Lin Yang and Ulhas Bhatt and Aruna Sambandam and Matthew Isherwood and Larry Yet and Michael T Herr and Sarah Ebeltoft and Carla Hassler and Linda Fleming and Anthony D Pechulis and Anne Payen Fornicola and Nicholas Holman and Dennis Milanowski and Ian Cotterill and Vadim Mozhaev and Yuri Khmelnitsky and Peter R Guzzo and Bruce J. Sargent and Bruce F Molino and Richard Olson and H Dalton King and Snjezana Lelas and Yu Wen Li and Kim Johnson and Thaddeus Molski and Anitra Orie and Alicia Ng and Roy Haskell and Wendy Clarke and Robert Bertekap and Jonathan O'Connell and Nicholas Lodge and Michael Sinz and Stephen Adams and ROBERT ZACZEK and John E. Macor},
title = {Design and Synthesis of 4-Heteroaryl 1,2,3,4-Tetrahydroisoquinolines as Triple Reuptake Inhibitors},
journal = {ACS Medicinal Chemistry Letters},
year = {2014},
volume = {5},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/ml500053b},
number = {7},
pages = {760--765},
doi = {10.1021/ml500053b}
}
Cite this
MLA
Copy
Liu, Shuang, et al. “Design and Synthesis of 4-Heteroaryl 1,2,3,4-Tetrahydroisoquinolines as Triple Reuptake Inhibitors.” ACS Medicinal Chemistry Letters, vol. 5, no. 7, May. 2014, pp. 760-765. https://doi.org/10.1021/ml500053b.