116103-16-3Relevant articles and documents
Design, synthesis, evaluation and QSAR analysis of N1-substituted norcymserine derivatives as selective butyrylcholinesterase inhibitors
Takahashi, Jun,Hijikuro, Ichiro,Kihara, Takeshi,Murugesh, Modachur G.,Fuse, Shinichiro,Kunimoto, Ryo,Tsumura, Yoshinori,Akaike, Akinori,Niidome, Tetsuhiro,Okuno, Yasushi,Takahashi, Takashi,Sugimoto, Hachiro
scheme or table, p. 1718 - 1720 (2010/06/19)
We synthesized a series of N1-substituted norcymserine derivatives 7a-p and evaluated their anti-cholinesterase activities. In vitro evaluation showed that the pyridinylethyl derivatives 7m-o and the piperidinylethyl derivative 7p improved the anti-butyrylcholinesterase activity by approximately threefold compared to N1-phenethylnorcymserine (PEC, 2). A quantitative structure-activity relationship (QSAR) study indicated that logS might be a key feature of the improved compounds.
Synthesis and Anticholinesterase Activity of (-)-N1-Norphysostigmine, (-)-Eseramine, and Other N(1)-Substituted Analogues of (-)-Physostigmine
Yu, Qian-Sheng,Atack, John R.,Rapoport, Stanley I.,Brossi, Arnold
, p. 2297 - 2300 (2007/10/02)
(-)-N1-Benzylnorphysostigmine (4), prepared from synthetic (-)-O-methyl-N1-noreseroline (1) by N-benzylation, ether cleavage, and reaction of (-)-N1-benzylnoreseroline (3) with methyl isocyanate, was the intermediate used to prepare the title compounds.Catalytic debenzylation of (4) afforded (-)-N1-norphysostigmine (5), and (-)-eseramine (6) was obtained by reaction of 5 with methyl isocyanate.Reductive N-methylation of 5 gave (-)-physostigmine (9) while reaction of 5 with allyl bromide and phenethyl bromide afforded carbamates 7 and 8, respectively.Data on the in vitro potencies (IC50) and activities of certain of these compounds (4-8) as inhibitors of electric eel acetyl cholinesterase are reported. (-)-N1-Norphysostigmine (5) was found to be similarly potent against AChE as (-)-physostigmine (9).
