86138-19-4

Upstream product

• 113997-50-5 1-(5-methoxyindol-3-yl)-2-nitropropane 
• 1006-94-6 5-methoxylindole 
• 192189-10-9 3-iodo-5-methoxyindole-1-carboxylic acid tert-butyl ester 
• 85092-86-0 3-iodo-5-methoxy-1H-indole 
• 4761-29-9 1-(5-methoxyindol-3-yl)-2-propanone 
• 113997-67-4 (S,S)-N-α-phenetyl-1-(5-methoxyindol-3-yl)-2-aminopropane 
• 113997-68-5 (R,S)-N-α-phenetyl-1-(5-methoxyindol-3-yl)-2-aminopropane 

Relevant academic research and scientific papers

COMPOUNDS AND METHOD OF USE

This present disclosure relates to compounds with ferroptosis inducing activity, a method of treating a subject with cancer with the compounds, and combination treatments with a second therapeutic agent.

Synthesis and serotonin receptor affinities of a series of enantiomers of α-methyltryptamines: Evidence for the binding conformation of tryptamines at serotonin 5-HT(1B) receptors

A procedure for the preparation of optically pure α-methyltryptamines (AMTs) from substituted indoles was developed. The key step in the sequence was the reductive amination of substituted indole-2-propanones with the commercially available pure enantiomers of α-methylbenzylamine, followed by the chromatographic separation of the resulting pair of diastereomeric amines by preparative centrifugal (Chromatotron) chromatography. Catalytic N-debenzylation then afforded the pure AMT enantiomers. Optical purity was established by chiral HPLC analysis of the 2-naphthoylamide derivatives. An improved procedure for the preparation of indole-2-propranone was also developed. To probe structure-activity relationships of serotonin receptors, affinities of the α-methyltryptamine enantiomers were then measured at the 5-HT2 antagonist receptor subtype, with displacement of [3H]ketanserin, and were estimated at the 5-HT(1B) receptor, with displacement of [3H]serotonin, respectively, in rat frontal cortex homogenates. Enantioselectivity at the receptor subtypes varied, depending on aromatic substituents. For a 5-hydroxy or 5-methoxy, the S enantiomer had higher affinity or was equipotent to the R enantiomer. This selectivity at [3H]serotonin binding sites was reversed for 4-oxygenated α-methyltryptamines, where a 4-hydroxy or 4-methoxy did not enhance affinity over the unsubstituted compounds. These results can be explained, for the [3H]serotonin displacement data, if the binding conformation is one where the ethylamine side chain is trans and lying in a plane perpendicular to the indole ring plane.