[Chemistry of A-2545, an anti-arrhythmia drug candidate. I. Structure elucidation of its main hydrolysis product].
A great number of antiarrhythmic agents with 2,2,5,5-tetramethyl-3-pyrroline (and pyrrolidine)-3-carboxamide structure were synthesized. One of them A-2545 (1) was selected for further investigation aiming the elucidation of its chemical properties. The hydrolysis of 1 was studied, where theoretically seven hydrolysis products might be formed (2-8, Fig.1.). The hydrolysis takes place in aqueous solution of 1. HCl also at room temperature. In alkali-catalyzed process only one main product can be detected by TLC. This hydrolysis product was assigned as phthalamide acid (2) proved by chromatographic, thermic, GC-MS and NMR methods. An interesting behaviour of 2 upon GC-MS investigation (thermic and electron impact) is its recyclisation to 1 at the injector temperature (140 degrees) thus 2 appears in the mass spectrum as it would be A-2545 (Fig. 2. and 3.).
Takács
M
M
Semmelweis Orvostudományi Egyetem, Gyógyszerészi Kémiai Intézet, Budapest.
Vámos
J
J
Tóth
G
G
Mikóné Hideg
Z
Z
D000889:Anti-Arrhythmia Agents / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D006868:Hydrolysis; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011758:Pyrroles / Q000737:chemistry*
D000889:Anti-Arrhythmia Agents; D011758:Pyrroles; C109568:A 2545