ChemInform Abstract: AZACYCLOALKANE 9. MITT. SYNTH. UND ANAESTESIERENDE WIRKUNG VON PYRROMECATIN UND CYCLOMECATIN

Abstract

Das aus Mesidin und dem entsprechenden Säurechlorid leicht herstellbare g Mesidid (I) läßt sich mit einem Überschuß an Butylamin oder Cyclohexylamin glatt zu den Pyrrolidinen Pyrromecain (IIIa) und Cyclomecain (IIIb) cyclisieren.

Synthesis, local anaesthetic and antiarrhythmic activities of N-alkyl derivatives of proline anilides

“…Lidocaine opened a new avenue for development of local anaesthetics and its structural features, such as tertiary amino group and arylamide moiety connected with one carbon atom, became a classical pattern for most of the modern local anaesthetics ( anaesthetics [8][9][10]. At the same time effective anaesthetics, derivatives of proline, namely cyclomecaine and pyromecaine were developed [11]. However, therapeutic application of these drugs is limited due to their substantial general toxicity [12] and associated side effects [13,14].…”

“…Herein we report synthesis and biological activity of N-alkyl derivatives of proline anilides, which can be considered as structural analogues of cyclomecaine, one of the most potent modern local anaesthetics [11,21]. Effects of two types of structural variations on the anaesthetic and antiarrhythmic activity were explored: (1) substituents on the phenyl ring of the anilide fragments and (2) type of alkyl group at the nitrogen atom of the proline fragment.…”