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

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)
View Full-Text   |   Download PDF [89 KB, uploaded 18 June 2014]   |  

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).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

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