Sinteza zaviralcev butirilholinesteraze na osnovi indola in naftalena

Krušič, Andreja (author), Grošelj, Uroš (mentor)

Iz N-(2-cikloheptiletil)-3-(1H-indol-3-il)propanamida sem v dveh korakih pripravila amin N-(3-(1H-indol-3-il)propil)-N-(2-cikloheptiletil)butan-1-amin (η = 30 %), ki sem ga uspešno pretvorila v amonijevo sol N-(3-(1H-indol-3-il)propil)-N-(2-cikloheptiletil)-N-metilbutan-1-amonijev jodid (η = 54 %). 1H-pirolo[2,3-b]piridin sem v dveh korakih pretvorila v 2-okso-2-(1H-pirolo[2,3-b]piridin-3-il)etanojsko kislino (η = 2 %). Iz naftalen-1- in naftalen-2-karbaldehida sem v štirih stopnjah pripravila ustrezna terciarna amina, N-(2-cikloheptiletil)-N-(3-(naftalen-1-il)propil)butan-1-amin (η = 5 %) in N-(2-cikloheptiletil)-N-(3-(naftalen-2-il)propil)butan-1-amin (η = 2 %). Končnim produktom smo določili stopnjo inhibicije humane butirilholinesteraze (hBChE).

• Language: Slovenian
• Keywords: zaviralci, butirilholinesteraza, indol, naftalen.
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2020
• PID: 20.500.12556/RUL-119406
• COBISS.SI-ID: 28329475
• Publication date in RUL: 08.09.2020

Secondary language

• Language: English
• Title: Synthesis of indole- and naphthalene-based butyrylcholinesterase inhibitors

Abstract

N-(2-Cycloheptylethyl)-3-(1H-indol-3-yl)propanamide was transformed in two synthetic steps into N-(3-(1H-indol-3-yl)propyl)-N-(2-cycloheptylethyl)butan-1-amine (η = 30 %), which was then successfully transformed into quaternary ammonium salt N-(3-(1H-indol-3-yl)propyl)-N-(2-cycloheptylethyl)-N-methylbutan-1-aminium iodide (η = 54 %). 1H-Pyrrolo[2,3-b]pyridine was transformed into 2-oxo-2-(1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid in two synthetic steps (η = 2 %). Naphthalene-1- and naphthalene-2-carbaldehyde were transformed in four synthetic steps into the corresponding tertiary amines, N-(2-cycloheptylethyl)-N-(3-(naphthalen-1-yl)propyl)butan-1-amine (η = 5 %) and N-(2-cycloheptylethyl)-N-(3-(naphthalen-2-yl)propyl)butan-1-amine (η = 2 %). Final products were tested for activity against human butyrylcholinesterase (hBChE).

• Keywords: inhibitors, butyrylcholinesterase, indole, naphthalene.