3-Phenyl-1-indanamines. Potential antidepressant activity and potent inhibition of dopamine, norepinephrine, and serotonin uptake.

doi:10.1021/JM00150A012

Paper

3-Phenyl-1-indanamines. Potential antidepressant activity and potent inhibition of dopamine, norepinephrine, and serotonin uptake.

Published Dec 1, 1985 · K. Bogeso, A. V. Christensen, J. Hyttel

Journal of medicinal chemistry

Q1 SJR score

115

Citations

3

Influential Citations

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Abstract

A series of 3-phenyl-1-indanamines was synthesized and tested for potential antidepressant activity and for inhibition of dopamine (DA), norepinephrine (NE), and serotonin (5-HT) uptake. Trans isomers were generally potent inhibitors of DA, NE, and 5-HT uptake, while cis isomers preferentially inhibited the uptake of 5-HT. The affinity for the DA-uptake site was very dependent on the aromatic substitution pattern where highest potency was found for 3',4'-dichloro substituted compounds (45). This substitution pattern also resulted in high affinity for the NE-and 5-HT-uptake sites, but potent 5-HT-uptake inhibiting activity could also be obtained with other substitution patterns. Only small amines could be accommodated at the 5-HT-uptake site while larger amines such as piperazine could be accommodated both at the DA-and NE-uptake sites. The observed structure-activity relationships were explained from the results of superimpositions of a trans (45) and cis (72) isomer with 5-HT and DA, respectively, in relation to a proposed three-point binding of the uptake inhibitors at the uptake sites. Finally, comparison of the structures of the 3-phenyl-1-indanamines with other newer bicyclic catecholamine- and/or serotonin-uptake inhibitors revealed common structural elements important for potent DA-, NE-, and/or 5-HT-uptake inhibition.

In Vitro Study

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Study Snapshot

3-phenyl-1-indanamines show potential antidepressant activity and potent inhibition of dopamine, norepinephrine, and serotonin uptake, with cis isomers preferentially inhibiting serotonin uptake.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

3-Phenyl-1-indanamines. Potential antidepressant activity and potent inhibition of dopamine, norepinephrine, and serotonin uptake.

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References

Citations

Asymmetric Hydrogenation of Exocyclic α,β-Unsaturated Nitriles: An Access to Chiral 2-Benzocyclic Acetonitriles and Ramelteon.

The Rh-JosiPhos complex efficiently hydrogenates exocyclic,-unsaturated nitriles, providing an efficient synthetic route to chiral 2-benzocyclic acetonitriles and the sleep agent (S)-Ramelteon.

Recent Progress in Metal‐Free Hydroacylation Reactions of Alkenes and Alkynes

Metal-free hydroacylation reactions have made significant progress in the synthesis of various bioactive molecules compared to conventional metal catalysts.

Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction

Bismuth(III) triflate is an efficient and environmentally friendly catalyst for the Nazarov reaction, leading to the synthesis of 3-aryl-2-ethoxycarbonyl-1-indanones and 3-aryl-1-indanones with promising biological properties against human cancer cells.

Synthesis of anti-depressant molecules via metal-catalyzed reactions: a review

Metal-catalyzed reactions play a crucial role in synthesizing key structural motifs in antidepressant drugs, offering potential for better therapies.

Investigation of the Effect of Indatraline on Oxidative Damage Induced by Hydrogen Peroxide in C6 Glioma Cell Line

Indatraline at doses of 10, 5, and 2.5 M significantly enhances cell survival and protects against oxidative damage caused by hydrogen peroxide in C6 glioma cells.