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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, 2,*  and 1
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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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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