African Journal of
Pure and Applied Chemistry

  • Abbreviation: Afr. J. Pure Appl. Chem.
  • Language: English
  • ISSN: 1996-0840
  • DOI: 10.5897/AJPAC
  • Start Year: 2007
  • Published Articles: 357

Full Length Research Paper

Synthesis, characterization and trypanocidal activity of some aromatic thiosemicarbazones and their 1,3,4-thiadiazolines derivatives

Houssou Raymond Fatondji1, Fernand Gbaguidi2*, Salomé Kpoviessi1, Joanne Bero3, Veronique Hannaert4, Joëlle Quetin-Leclercq3, Jacques Poupaert3, Mansourou Moudachirou2 and Georges Coffi Accrombessi1
1Laboratoire de Chimie Organique Physique et de Synthèse, Université d’Abomey-Calavi, Faculté des Sciences et Techniques Cotonou BP 4521, Republic of Bénin. 2Laboratoire National de Pharmacognosie/Centre Béninois de la Recherche Scientifique et Technique (CBRST), Bp 06 Oganla Porto-Novo, Republic of Bénin. 3Louvain Drug Research Institute (LDRI) 73.40 B-1200 Brussels-Belgium, 72.30 B-1200 Brussels-Belgium. 4Institut de Pathologie Cellulaire Christian Duve (ICP) 73.30 B-1200 Brussels-Belgium
Email: [email protected]

  •  Accepted: 17 February 2011
  •  Published: 30 April 2011

Abstract

The thiosemicarbazones of six aromatic ketones were synthesized as well as their 1,3,4-thiadiazolines derivatives obtained by cyclization under acetylating condition with yields going from 40 to 90%. The products purity was confirmed by mass spectrometry coupled with high-performance liquid chromatography (LC/MS) and there were characterized using spectrometry IR, NMR 1H and 13C (nuclear magnetic resonance). These compounds were then tested in vitro on Trypanosoma brucei brucei according to the “LILIT, Alamar Blue” method for a comparison of their trypanocidal activity. Thus, all thiosemicarbazones appeared much more active than their corresponding 1,3,4-thiadiazolines. Thiosemicarbazone 6a (IC50 = 9.62 µM) was the most active of all thiosemicarbazones tested and it is the same for its thiadiazoline 6b (IC50 = 49.03 µM) among 1,3,4-thiadiazolines.

 

Key words: Thiosemicarbazone, 1,3,4-thiadiazolines, characterization, trypanocidal activity.