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




β–Cyclodextrin–Propyl Sulfonic Acid Catalysed One-Pot Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles as Local Anesthetic Agents - Download this document for free, or read online. Document in PDF available to download.

1

Zhongnan Hospital of Wuhan University, Department of Anesthesiology, Wuhan University, Wuhan 430071, China

2

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

Abstract 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





Author: Yan Ran 1,†, Ming Li 2,† and Zong-Ze Zhang 1,*

Source: http://mdpi.com/



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