Synthesis of 1-Aryl-3-phenethylamino-1-propanone hydrochlorides as possible potent cytotoxic agents.
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.
Mete
Ebru
E
Department of Chemistry, Faculty of Arts and Sciences, Ataturk University, 25240, Erzurum, Turkey.
Gul
Halise Inci
HI
Kazaz
Cavit
C
D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008352:Mannich Bases / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D003603:Cytotoxins; D008352:Mannich Bases