Synthesis and anthelmintic activity of some hybrid
Benzimidazolyl-chalcone derivatives
Mahama Ouattara1*,
Drissa Sissouma2, Mamidou W Koné3,4,
Hervé E Menan5, Seikou A Touré2
and Lassina Ouattara1
1Laboratoire
de Chimie Thérapeutique et Synthèse de Médicaments, UFR
Sciences Pharmaceutiques et Biologiques, Université de
Cocody. 01 BP V 34 Abidjan, Côte d’Ivoire, 2Laboratoire
de Chimie Organique Structurale, UFR SSMT, Université de
Cocody. 22 BP 582 Abidjan, Côte d’Ivoire, 3Centre
Suisse de Recherches Scientifiques en Côte d'Ivoire. 01
BP 1303 Abidjan, 4UFR Sciences de la Nature,
Université d’Abobo-Adjamé. 02 BP 801 Abidjan, Côte
d’Ivoire, 5Laboratoire de Parasitologie et
Mycologie, UFR Sciences Pharmaceutiques et Biologiques,
Université de Cocody. 01 BP V 34 Abidjan, Côte d’Ivoire.
For correspondence:
E-mail:
mahama.dpm@gmail.com;
mahama.ouattara@univ-cocody.ci
Tel: +225
08741023
Received: 9 May
2011 Revised
accepted: 2 November, 2011
Tropical
Journal of Pharmaceutical Research, December 2011;
10(6): 767-775
http://dx.doi.org/10.4314/tjpr.v10i6.10
Abstract
Purpose:
To
synthesize hybrid benzimidazolyl-chalcone derivatives,
evaluate their anthelmintic activity, and establish some
structural elements which could lead to induction and
enhancement of this activity.
Methods:
A
series of
1-(1H-benzimidazol-2-yl)-3-aryl-2-propen-1-one
compounds (6a-z)
was synthesized by
condensation reaction of
2-acetylbenzimidazole with aryl and heteroaryl aldehyde
derivatives. The physicochemical
characterization of these benzimidazolyl-chalcones was
carried out by nuclear magnetic resonance spectroscopy (1H
and 13C NMR) and mass spectroscopy (MS). All
compounds were screened in vitro for their nematicidal
activity against Haemonchus contortus in larval
development assay.
The anthelmintic
activities
obtained were
compared with
those of
anthelmintic
reference
drugs (fenbendazole and
ivermectin); 1,3-diphenyl-2-propen-1-one
also
used as
reference for
chalcone.
Results:
Compounds 6a, 6g, 6w and 6y showed good
nematicidal activity
(LC100)
at
0.002 and 0.0092 µg/ml.
The
activity of these four benzimidazolyl-chalcones is
nearly equal to that of fenbendazole. It is also
interesting to know that these compounds have anti-haemonchus
activity
which
is equal or more efficient than ivermectin.
Four other compounds (6d,
6h, 6o and 6t) possess interesting anthelmintic
activities at 0.68 and 0.16 µg/ml.
Conclusion:
Preliminary structure-activity relationship studies
revealed that
arylpropenone group in position 2 of the benzimidazole
ring
can
be considered
as new
pharmacophore for
nematicidal activity.
Keywords:
Benzimidazole, Chalcone, Anthelmintic activity,
Haemonchus contortus.
