S. Adamovich, A. N. Mirskova, R. G. Mirskov
Nov 1, 2012
Citations
0
Influential Citations
3
Citations
Journal
Russian Chemical Bulletin
Abstract
Acetylcholine, an endogenous neurotransmitter, per forms one of the most vital functions in a living organism by promoting neuromuscular transmission from its brain and central nervous system to effector organs. This com pound has ionic liquid structure and is commonly used as the chloride (MeCOOCH2CH2N Me3)•Cl –, which is the first representative of so called cholinomimetics. The drugs of this group include succinic (succinylchol ine, Quelicin) and carbamic acid esters (carbacholine).1 Another group of drugs that block cholinergic transmission is constituted by cholinolytics containing aryl substitu ents in the ester group. They include [2 (2 hydroxy 2,2 diphenylacetoxy)ethyl]trimethylammonium iodide [Ph2C(OH)COOCH2CH2N Me3]•I – (metacin), spas molytin, arpenal, and thiphen.1 In the present work, starting from (2 hydroxyethyl) dimethylamine (1) and various acyl chlorides RC(O)Cl (R = 2 methylphenoxymethyl (2), 4 chlorophenylsul fanylmethyl (3), 4 chlorophenylsulfonylmethyl (4), indol 3 ylsulfanylmethyl (5), and 1 benzylindol 3 ylsulfanyl methyl (6)2—4), we synthesized new analogs of acetylchol ine with potential biological activity. The products ob tained contain either protonated cations and the Cl– an ion (ionic liquids 7—11, m.p. 75—100 C) or alkylated cations and the I– anion (salts 12—16, m.p. 160—193 C) (Scheme 1).