Synthesis of 1-aryl-3-phenethylamino-1-propanone hydrochlorides as possible potent cytotoxic agents

METE E., GÜL H. İ., KAZAZ C.

MOLECULES, cilt.12, sa.12, ss.2579-2588, 2007 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 12 Sayı: 12
  • Basım Tarihi: 2007
  • Doi Numarası: 10.3390/12122579
  • Dergi Adı: MOLECULES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2579-2588
  • Anahtar Kelimeler: acetophenone, mono-Mannich base, prodrug, spectral analyses, synthesis, BIS MANNICH-BASES, JURKAT CELLS, CELLULAR GLUTATHIONE, CORRESPONDING PIPERIDINOLS, ANTIINFLAMMATORY ACTIVITY, ANTIMICROBIAL EVALUATION, ANTICONVULSANT ACTIVITY, ANTIFUNGAL ACTIVITY, DERIVATIVES, ACETOPHENONE
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.