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1 2005

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Geometry of Lidocaine-like Molecules: 3. Structure of a Potent Antiarrhythmic Agent: 2-Methyl-2-(1-morpholinyl)-N-(2,6-dimethylphenyl) acetamide

Główka M., Olczak A., Białasiewicz W., Kwapiszewski W.

Polish Journal of Chemistry

2005

Vol. 79 / nr 6

1079-1085

Crystal structure of an alanylyl analog of lidocaine with its amine function incorporated into morpholine ring and showing promising type I antiarrhythmic activity was studied in form of free base and hydrochloride. Crystal data: free base a = 9.498(2), b = 11.716(2), c = 13.497(2); hydrochloride a = 10.820(1), b = 11.971(3), c = 12.564(1); both P212121 (Z = 4); R1 = 0.039 and 0.037, respectively. Substitution at C alfa and incorporation of N amine atom into the aliphatic morpholinic ring significantly change conformational preference around C alfa-C(O) and C alfa-N(ring) bonds, as compared with parent lidocaine. The most interesting conformational change observed was that the title molecule in the protonated form (being probably the biologically active) has gauche orientation of _N-H(amine) bond in relation to C=O group, while all other structures have different orientations, either antiperiplanar or synperiplanar (unprotonated lidocaine only). And the two groups are crucial for hydrogen bonds formation with a perspective receptor of type I antiarrhythmics.