Next Article in Journal
Substituted N-Phenylpyrazine-2-carboxamides, Their Synthesis and Evaluation as Herbicides and Abiotic Elicitors
Next Article in Special Issue
Efficacy of DA-7218, a New Oxazolidinone Prodrug, in the Treatment of Experimental Actinomycetoma Produced by Nocardia brasiliensis
Previous Article in Journal
Essential Oils of Satureja Species: Insecticidal Effect on Culex pipiens Larvae (Diptera: Culicidae)
Previous Article in Special Issue
The Drug Release Profile from Calcium-induced Alginate Gel Beads Coated with an Alginate Hydrolysate
Article Menu

Export Article

Open AccessArticle
Molecules 2007, 12(12), 2579-2588;

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

Department of Chemistry, Faculty of Arts and Sciences, Ataturk University, 25240, Erzurum, Turkey
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)
Full-Text   |   PDF [89 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: Acetophenone; mono-Mannich base; prodrug; spectral analyses; synthesis. Acetophenone; mono-Mannich base; prodrug; spectral analyses; synthesis.

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top