Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides As Possible Potent Cytotoxic Agents

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2008 Feb 9

PMID 18259144

Citations 1

Authors

Ebru Mete

Halise Inci Gul

Cavit Kazaz

Affiliations

Soon will be listed here.

Abstract

1-Aryl-3-phenethylamino-1-propanone hydrochlorides 1-10, which are potentialpotent cytotoxic agents, were synthesized via Mannich reactions using paraformaldehyde,phenethylamine hydrochloride as the amine component and acetophenone, 4'-methyl-, 4'-methoxy-, 4'-chloro-, 4'-fluoro-, 4'-bromo-, 2',4'-dichloro-, 4'-nitro-, 4'-hydroxyacetophenone or 2-acetylthiophene as the ketone component. Yields were in the87-98 % range. Of the compounds synthesized, compounds 2, 6-8 and 10 were new. Theoptimum reaction conditions were investigated by changing the mol ratios of the reactants,the solvents and the acidity levels using 1 and 10 as representative targets. It was observedthat the best mol ratio of the ketone, paraformaldehyde and phenethylamine hydrochloridewas 1:1.2:1 (compared with a 2:2.1 ratio), and the most suitable reaction medium wasethanol containing concentrated hydrochloric acid (compared with only ethanol or nosolvent). This study may serve as a guide for the conditions of the reactions to synthesizecompounds having similar chemical structures.

Citing Articles

Mannich bases in medicinal chemistry and drug design.

Roman G Eur J Med Chem. 2014; 89:743-816.

PMID: 25462280 PMC: 7115492. DOI: 10.1016/j.ejmech.2014.10.076.

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