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

Abstract

1-Aryl-3-phenethylamino-1-propanone hydrochlorides 1-10, which are potential potent 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 the 87-98 % range. Of the compounds synthesized, compounds 2, 6-8 and 10 were new. The optimum 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 observed that the best mol ratio of the ketone, paraformaldehyde and phenethylamine hydrochloride was 1:1.2:1 (compared with a 2:2.1 ratio), and the most suitable reaction medium was ethanol containing concentrated hydrochloric acid (compared with only ethanol or no solvent). This study may serve as a guide for the conditions of the reactions to synthesize compounds having similar chemical structures.

Synthesis and Antifungal Activity of 1‐Aryl‐3‐phenethylamino‐1‐propanone Hydrochlorides and 3‐Aroyl‐4‐aryl‐1‐phenethyl‐4‐piperidinols

“…The chemial structures of the compounds were confirmed by 1 H-NMR, 13 C-NMR, UV, IR, and MS spectra and the purity level of the compounds was determined by elemental analyses. The spectral data of the mono-Mannich bases were reported in our previous study [50] and the spectral data for the piperidinol compounds are shown in Tables 1 and 2. The results of the elemental analyses for the piperidinols, which are reported here for the first time, are shown in Table 3.…”

“…The optimal reaction conditions for the synthesis of these compounds, 1-aryl-3-phenethylamino-1-propanone hydrochlorides, were investigated by changing the molar ratios of reactants and solvent, and the acidity level of the reaction medium using compound 1a and 9a as representative compounds from our previous paper [50]. It has been reported that the most suitable mol ratio of the reactants was 1:1.2:1, compared with 2:2:1 suitable for ketone, paraformaldehyde, and phenethylamine hydrochloride.…”

“…The mono-Mannich bases 1a-9a reported in this study were synthesized as described in our previous study by the classical Mannich reaction in an acidic solution of ethanol under reflux conditions [50]. The optimal reaction conditions for the synthesis of these compounds, 1-aryl-3-phenethylamino-1-propanone hydrochlorides, were investigated by changing the molar ratios of reactants and solvent, and the acidity level of the reaction medium using compound 1a and 9a as representative compounds from our previous paper [50].…”

Evaluation of Physical, Thermal and Spectroscopic Properties of Biofield Treated p-Hydroxyacetophenone

“…It acts as a precursor for the synthesis of p-hydroxyacetanilide and paracetamol (analgesic drug) [7]. It is also used as a ketone component in the manufacturing of 1-aryl-3-phenethylamino-1-propanone hydrochloride that is a potent cytotoxic agent [8]. Moreover, they are also used in manufacturing of cosmetics, flavours, and fragrances [9].…”

A New Mannich Base N-[Phenyl(pyrrolidin-1- Yl)methyl]acetamide - Synthesis, Spectral Properties, Antibacterial and Antifungal Studies of Some of Its Metal Complexes

“…[11][12][13][14] Furthermore, coordination compounds with transition metals have been investigated in the last few decades after the discovery of cisplatin because they have shown good antineoplastic activity and less toxicity. [15,16] Literature survey shows that a large number of transition metal complexes of amides have been found to be associated with diverse pharmacological activities. [17] Complexes of transition metals with amides in proteins and peptides are utilized in numerous biological processes, such as oxygen conveyer, electron transfer and oxidation.…”