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EN
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.
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