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Molecules 2007, 12(12), 2579-2588; doi:10.3390/12122579

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

1
Department of Chemistry, Faculty of Arts and Sciences, Ataturk University, 25240, Erzurum, Turkey
2
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, 25240, Erzurum, Turkey
*
Author to whom correspondence should be addressed.
Received: 29 October 2007 / Revised: 26 November 2007 / Accepted: 10 December 2007 / Published: 12 December 2007
(This article belongs to the Special Issue Prodrugs)
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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.
Keywords: Acetophenone; mono-Mannich base; prodrug; spectral analyses; synthesis. Acetophenone; mono-Mannich base; prodrug; spectral analyses; synthesis.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Mete, E.; Gul, H.I.; Kazaz, C. Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides as Possible Potent Cytotoxic Agents. Molecules 2007, 12, 2579-2588.

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