Synthesis of 2-[[1-oxo-2-(substituted amino)propyl]amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-carboxylic acid ethyl esters as potential local anesthetic agents.
The synthesis of a series of 10 compounds related to 2-[[1-oxo-2-substituted amino)propyl]amino]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-carboxyli c acid ethyl esters (III-XII) that are structurally-related to carticaine and the results of a study of their biological activity are reported. Most of the these compounds showed significant activity at lower concentrations when evaluated for local anesthetic activity using the frog-foot withdrawal reflex, the guinea pig wheal derm and the rabbit corneal reflex tests. Compounds III, V, VII and X displayed the shortest onset times and the longest duration of activity, compared to the model drug lidocaine.
al-Obaid
A R
AR
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia.
D000779:Anesthetics, Local / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D002355:Carticaine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003315:Cornea / Q000187:drug effects; D006168:Guinea Pigs; D008012:Lidocaine / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D010147:Pain Measurement / Q000187:drug effects; D011817:Rabbits; D011894:Rana pipiens; D012018:Reflex / Q000187:drug effects; D012882:Skin Tests
D000779:Anesthetics, Local; D008012:Lidocaine; D002355:Carticaine