88301-74-0Relevant articles and documents
Synthesis, sciatic nerve block activity evaluation and molecular docking of fluoro-substituted lidocaine analogs as local anesthetic agents
Li, Wen,Yan, Ying,Chang, Yingjie,Ding, Lina,Liu, Hongmin,You, Qidong
, p. 1783 - 1795 (2019/08/12)
Thirty fluoro-substituted lidocaine analogs (10a–e, 11a–e, 14a–e, 15a–e, 18a–e and 19a–e) were synthesized, and their sciatic nerve block activity were evaluated as local anesthesia. Most of the compounds displayed significant potency, and compound 10a in particular was much more potent than the parent lidocaine. Fifteen analogs including 10a demonstrated pKa values of 7.5–7.8 suitable for local anesthesia. Compound 10a, 14e, and lidocaine were docked into three target receptors of local anesthetics by molecular docking studies to delineate structure-activity relationships and explain the differences in activities. Hydrophobic interactions and hydrogen bonds were identified key to molecular binding, suggesting that optimization of these interactions and/or trifluoro-substitution at the benzene ring of lidocaine could enhance the properties of lidocine analogs for local anesthesia.
Behavior of Benzyl Sulfoxides toward Acid Chlorides. Useful Departures from the Pummerer Reaction
Chupp, John P.,Balthazor, Terry M.,Miller, Michael J.,Pozzo, Mark J.
, p. 4711 - 4716 (2007/10/02)
The present study extends the reaction of certain electrophilic reagents with electron-rich sulfides and sulfoxides beyond previously known limits.Thus, treatment of methoxy- and, more particularly, aminobenzyl sulfoxides 2 with acyl or hydrogen chlorides gives rise in high yields to the corresponding benzyl chlorides, a departure from the normally expected Pummerer reaction.It is demonstrated that ideal substrates for this reaction are o-anilines 1 derived from the well-known rearrangment of aromatic sulfilimines.Further, certain of the o-ammoniobenzyl chloride salts 4 so produced provide a basis for a novel and superior desulfurization of 1 to the corresponding o-methylaniline without resorting to Raney nickel.
