A. M. Likhosherstov, O. Filippova, V. P. Peresada
Jun 10, 2003
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0
Influential Citations
14
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Journal
Pharmaceutical Chemistry Journal
Abstract
Previously, it was demonstrated that many piperazine derivatives possess antiarrhythmic properties [1, 2]. Here we report on the synthesis and antiarrhythmic activity of a series of 2-[(2 -hydroxy-2 -R)-ethyl]-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazines (IVa – IVg). The new compounds were synthesized according to the following scheme. In the first step, boiling 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine (I) [3] with epoxy compounds II in isopropyl alcohol or benzene yields the corresponding amino alcohols III. These products appear as viscous high-boiling oils insoluble in water and soluble in organic solvents. The reaction between amino alcohols III and fumaric acid in alcohol solutions yields fumarates IV, which are crystalline substances soluble in water and insoluble in ether and benzene. The proposed structures were confirmed by the results of elemental analyses and spectroscopic measurements. For example, the H NMR spectrum of compound IVg contains the following signals: three multiplets (at = 6.51, 6.3, and 5.84 ppm) from protons (6-H, 7-H, and 8-H, respectively) of the pyrrole ring, two multiplets ( = 3.60 – 4.0 ppm) from protons at C-3,4 of the pyrazine ring, two multiplets ( = 2.6 – 3.05 ppm) from protons at C-1 of the pyrazine ring, a multiplet ( = 2.55 – 2.65 ppm) from the proton at C -1, a multiplet ( = 4.73 ppm) from the protons at C -2, and a multiplet ( = 7.20 – 7.40 ppm) from protons of the phenyl ring.