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. 2013 May 15;23(10):2948-50.
doi: 10.1016/j.bmcl.2013.03.045. Epub 2013 Mar 26.

Conformationally restricted homotryptamines. Part 6: indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors

Jonathan L Ditta  1 , Derek J Denhart, Jeffrey A Deskus, James R Epperson, Zhaoxing Meng, Qi Gao, Gail K Mattson, Mellissa A Lapaglia, Matthew T Taber, Thaddeus F Molski, Nicholas J Lodge, Ronald J Mattson, John E Macor
Affiliations

Conformationally restricted homotryptamines. Part 6: indole-5-cycloalkyl methylamines as selective serotonin reuptake inhibitors

Jonathan L Ditta et al. Bioorg Med Chem Lett. .

Abstract

Racemic 5-(trans-2-aminomethylcyclopropyl)indoles, 5-(trans-2-aminomethylcyclopentyl) indoles, and 5-(cis-2-aminomethylcyclopentyl)indoles were synthesized and evaluated as selective serotonin reuptake inhibitors. These analogs followed SAR trends similar to those previously reported for 3-cycloalkyl substituted indoles. The most potent analogs exhibited single digit nanomolar inhibition at the human serotonin transporter but were 10-fold less active than the previously reported compounds.

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