Synthesis and Potential Trypanocidal Activity of N, N-disubstituted-3-(1-benzenesulphonylindol- 2-yl and -3-yl) propagylamines

Abstract

The synthesis of N, N-disubstituted –3-( 1-benzenesulphonylindol- 2-yl and 3-yl) propagylamines by cuprous catalyzed Mannich reaction of 2 and 3, 1-(1-benzenesulphonyl-indol)ethynes and secondary amines in ethanol at reflux temperature afforded the compounds 4-methylpiperazinomethyl-2-(1-benzenesulphonylindol-2-yl)ethyne (1), 4-methylpiperazinomethyl-2-(1-benzenesulphonylindol-3-yl)ethyne (2a), 4-methyl-piperazinomethyl-2-(1-benzenesulphonyl-5-methoxyindol-3yl)ethyne (2b), morpholino-2-(benzenesulphonylindol-3yl)ethyne (3a), morpholino-2-(1-benzenesulphonyl-5-methoxy-indol-3-yl)ethyne (3b) and N-carboxyethoxymethyl-3-(1- benzenesulphonylindol-3yl)ethyne (4) in good yields. All these compounds were fully characterized by means of Infrared spectroscopy, Nuclear Magnetic Resonance (1H) and Mass spectrometry, and elemental analyses. Their potential trypanocidal activity was evaluated in vitro against Trypanosoma brucei brucei (S427/118 Mi Tat 1.5) and compound 1 was found to be the most active. This study has therefore established typical synthetic procedures for the new N, N-disubstituted -3-(1-benzenesulphonylindol-2-yl and -3-yl) propagylamines and furnished their spectral analysis.

Keywords: Propagylamines, spectral analysis, synthesis, trypanocidal activity

East and Central African Journal of Pharmaceutical Sciences Vol. 13 (2010) 72-77