Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs)

Bioorganic & Medicinal Chemistry Letters
2005.0

Abstract

A series of N,N-dimethylhomotryptamines was prepared and their binding affinities at the serotonin transporter (SERT) were determined. Compounds possessing an electron withdrawing substituent at the C5-position of the indole nucleus were found to be potent SSRIs. Initial attempts at conformational restriction of the propylamine sidechain by incorporation of a quinuclidine bicyclic structure did not improve binding affinity at SERT.

Knowledge Graph

Similar Paper

Homotryptamines as potent and selective serotonin reuptake inhibitors (SSRIs)
Bioorganic & Medicinal Chemistry Letters 2005.0
Conformationally Restricted Homotryptamines. 2. Indole Cyclopropylmethylamines as Selective Serotonin Reuptake Inhibitors
Journal of Medicinal Chemistry 2005.0
Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles
Bioorganic & Medicinal Chemistry Letters 2010.0
New indole derivatives as potent and selective serotonin uptake inhibitors
Journal of Medicinal Chemistry 1993.0
Structure–activity relationships of the 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ol series of monoamine reuptake inhibitors
Bioorganic & Medicinal Chemistry Letters 2009.0
Synthesis and serotonin receptor affinities of a series of enantiomers of .alpha.-methyltryptamines: evidence for the binding conformation of tryptamines at serotonin 5-HT1B receptors
Journal of Medicinal Chemistry 1988.0
Structure−Activity Relationships for a Novel Series of Citalopram (1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile) Analogues at Monoamine Transporters
Journal of Medicinal Chemistry 2010.0
1-Naphthyl and 4-indolyl arylalkylamines as selective monoamine reuptake inhibitors
Bioorganic & Medicinal Chemistry Letters 2009.0
Design and Synthesis of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (Citalopram) Analogues as Novel Probes for the Serotonin Transporter S1 and S2 Binding Sites
Journal of Medicinal Chemistry 2013.0
2,3-Dihydro and carbocyclic analogs of tryptamines: interaction with serotonin receptors
Journal of Medicinal Chemistry 1982.0