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Molecules 2015, 20(11), 20286-20296;

β–Cyclodextrin–Propyl Sulfonic Acid Catalysed One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles as Local Anesthetic Agents

Zhongnan Hospital of Wuhan University, Department of Anesthesiology, Wuhan University, Wuhan 430071, China
Department of Doppler Ultrasound, PLA421 Hospital, Guangzhou 510318, China
These authors contributed equally to this work.
Author to whom correspondence should be addressed.
Academic Editors: Derek J. McPhee and Maria Emília de Sousa
Received: 5 September 2015 / Accepted: 7 October 2015 / Published: 12 November 2015
(This article belongs to the Section Medicinal Chemistry)
Full-Text   |   PDF [2349 KB, uploaded 12 November 2015]   |  


Some functionalized 1,2,4,5-tetrasubstituted imidazole derivatives were synthesized using a one-pot, four component reaction involving 1,2-diketones, aryl aldehydes, ammonium acetate and substituted aromatic amines. The synthesis has been efficiently carried out in a solvent free medium using β-cyclodextrin-propyl sulfonic acid as a catalyst to afford the target compounds in excellent yields. The local anesthetic effect of these derivatives was assessed in comparison to lidocaine as a standard using a rabbit corneal and mouse tail anesthesia model. The three most potent promising compounds were subjected to a rat sciatic nerve block assay where they showed considerable local anesthetic activity, along with minimal toxicity. Among the tested analogues, 4-(1-benzyl-4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline (5g) was identified as most potent analogue with minimal toxicity. It was further characterized by a more favourable therapeutic index than the standard. View Full-Text
Keywords: synthesis; imidazoles; local anesthetic agent synthesis; imidazoles; local anesthetic agent

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Ran, Y.; Li, M.; Zhang, Z.-Z. β–Cyclodextrin–Propyl Sulfonic Acid Catalysed One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles as Local Anesthetic Agents. Molecules 2015, 20, 20286-20296.

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