Next Article in Journal
Derinat Protects Skin against Ultraviolet-B (UVB)-Induced Cellular Damage
Previous Article in Journal
Evaluation of the Cytotoxicity of α-Cyclodextrin Derivatives on the Caco-2 Cell Line and Human Erythrocytes
Open AccessArticle

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

by Yan Ran 1,†, Ming Li 2,† and Zong-Ze Zhang 1,*
1
Zhongnan Hospital of Wuhan University, Department of Anesthesiology, Wuhan University, Wuhan 430071, China
2
Department of Doppler Ultrasound, PLA421 Hospital, Guangzhou 510318, China
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editors: Derek J. McPhee and Maria Emília de Sousa
Molecules 2015, 20(11), 20286-20296; https://doi.org/10.3390/molecules201119696
Received: 5 September 2015 / Accepted: 7 October 2015 / Published: 12 November 2015
(This article belongs to the Section Medicinal Chemistry)
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
Show Figures

Graphical abstract

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Article Access Map by Country/Region

1
Only visits after 24 November 2015 are recorded.
Back to TopTop