ChemInform Abstract: Choline Esters of N‐Substituted Amino Acids. Part 2. Synthesis of Dialkylaminoalkyl Esters of N‐Substituted αβ‐Dehydroamino Acids.

Topuzyan, V. O.; Gerasimyan, D. A.; Edilyan, A. S.; Mndzhoyan, O. L.

doi:10.1002/chin.198702147

Cited by 1 publication

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“…Previously, we have developed a method for the synthesis of such compounds [2,4], which is based on the interaction of unsaturated oxazolones with a-dimethylaminoethanol (at a 1 : 4 reactant ratio) under conditions of boiling for 7 -20 h in chloroform. The main disadvantages of this method are the low reaction rate and the need for a large excess of aminoalcohol, which complicates isolation and purification of the target products (the yields varied within 67 -88%).…”

Section: Experimental Chemical Partmentioning

confidence: 99%

Synthesis and anticholinesterase activity of 2-(dimethylamino)ethyl and choline esters of n-substituted α, β-dehydroamino acids

Grigoryan¹,

Ambartsumyan²,

Mkrtchyan

et al. 2006

Pharm Chem J

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A new method for the synthesis of tertiary and quaternary aminoesters of N-substituted a,b-dehydroamino acids is described. A series of 16 dehydroamino acids esterified to choline or to its tertiary analog have been synthesized by the proposed method with a yield of 84 -93%, and their interactions with human erythrocyte acetylcholinesterase (ACE) and human plasma butyrylcholinesterase (BCE) has been studied. The half-inhibiting concentrations IC 50 of the synthesized compounds (determined with respect to cholinesterase hydrolysis of a model substrate, 0.1 mM ATC) vary within a broad range (0.16 -1840 mM). The values of traditional parameters of the wave functions of ligands estimated using the Hartree -Fock method do not explain the observed pattern of the anticholinesterase activity. The specific properties of the molecules, especially in their quaternary ammonium salt forms, are probably related to their structural features, in particular, to the ability of the inhibitors to form cyclic conformations (so-called crown structures). Such structures are probably stabilized as a result of the formation of intramolecuar hydrogen bonds between protons of the choline residue and oxygen of the terminal peptide group. 135 0091-150X/06/4003-0135

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Section: Experimental Chemical Partmentioning

confidence: 99%