Conformationally restricted homotryptamines. Part 5: 3-(trans-2-aminomethylcyclopentyl)indoles as potent selective serotonin reuptake inhibitors.
A series of racemic 3-(trans-2-aminomethylcyclopentyl)indoles was synthesized and found to have potent binding to the human serotonin transporter (hSERT). The most active analog was synthesized stereospecifically and the active enantiomer was shown to have high affinity binding to hSERT.
Denhart
Derek J
DJ
Bristol-Myers SquibbPharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT 06492-7660, USA. derek.denhart@bms.com
Deskus
Jeffrey A
JA
Ditta
Jonathan L
JL
Gao
Qi
Q
Dalton King
H
H
Kozlowski
Edward S
ES
Meng
Zhaoxing
Z
LaPaglia
Melissa A
MA
Mattson
Gail K
GK
Molski
Thaddeus F
TF
Taber
Matthew T
MT
Lodge
Nicholas J
NJ
Mattson
Ronald J
RJ
Macor
John E
JE
D000818:Animals; D000928:Antidepressive Agents / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods; D003517:Cyclopentanes / Q000737:chemistry; D004305:Dose-Response Relationship, Drug; D006801:Humans; D007211:Indoles / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D008024:Ligands; D008956:Models, Chemical; D011485:Protein Binding; D051381:Rats; D012701:Serotonin / Q000737:chemistry; D017367:Selective Serotonin Reuptake Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014363:Tryptamines / Q000737:chemistry*
D000928:Antidepressive Agents; D003517:Cyclopentanes; D007211:Indoles; D008024:Ligands; D012701:Serotonin; D017367:Selective Serotonin Reuptake Inhibitors; D014363:Tryptamines