Tropical Journal of Pharmaceutical Research

Original Research Article | OPEN ACCESS

Synthesis and anthelmintic activity of some hybrid Benzimidazolyl-chalcone derivatives

Mahama Ouattara¹ , Drissa Sissouma², Mamidou W Koné^3,4, Hervé E Menan⁵, Seikou A Touré², Lassina Ouattara¹

¹Laboratoire de Chimie Thérapeutique et Synthése 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, UniversitÃ© de Cocody. 01 BP V 34 Abidjan, CÃ´te dâ€™Ivoire.

For correspondence:- Mahama Ouattara Email: mahama.dpm@gmail.com Tel:+22508741023

Received: 9 May 2011 Accepted: 2 November, 2011 Published: 25 December 2011

Citation: Ouattara M, Sissouma D, Koné MW, Menan HE, Touré SA, Ouattara L. Synthesis and anthelmintic activity of some hybrid Benzimidazolyl-chalcone derivatives. Trop J Pharm Res 2011; 10(6):767-775 doi: 10.4314/tjpr.v10i6.10

© 2011 The authors.
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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