Synthesis and antibacterial activity of 3-substituted-5H-4-oxo-1,2,3-triazino[5,4-b]indoles and 1,1-dialkyl(1-aryl)-3-(2-ethoxycarbonylindol-3-yl)triazenes

Structural Modifications of 3-Triazeneindoles and Their Increased Activity Against Mycobacterium tuberculosis

“…A series of new 1,1-dialkyl-3-[2-(ethoxycarbonyl) indol-3-yl]triazenes, "triazene ethyl esters", (ECIT), (TU214, 236, 250, 251, 276, 289, 300), as well as the previously described [7] compound TU112 (Table 1), incorporating N-methylpiperazine and related congeners, were synthesized as described earlier [12,13] by the N-N cross coupling reactions of appropriate 2-ethoxycarbonyl-3-diazo-3H-indoles (ECDI), at a large excess (ratio = 1:10) of appropriate piperazines or diethanolamine. A set of new 1,1-dialkyl-3-[2-(octyloxycarbonyl) indol-3-yl]triazenes (TU 281, 282, 290, 311) "triazene octyl esters" (OCIT) were synthesized analogously by the N-N cross coupling reactions of appropriate 2-octyloxycarbonyl-3-diazo-3H-indoles (OCDI) at a large excess (ratio = 1:10) of appropriate piperazines.…”

“…Initial 2-octyloxycarbonyl indoles required for the synthesis of OCDI were obtained by the Fisher indole synthesis followed by alkaline hydrolysis and subsequent p-toluenesulfonic acid-catalyzed esterification of appropriate indole-2-carboxylic acids with 1-octanol, as described [14]. Chemical structures of compounds were supported by elemental analyses, 1 H-NMR, 13 C-NMR and ESI-HRMS spectral data.…”

“…IR spectra were run as KBr disks on an IR-Fourier-spectrometer Magna 750 IR Nicolet. 1 H NMR (300, 400 or 600 MHz) and 13 C NMR (75, 101 or 151 MHz) spectra were recorded using Bruker Avance TM -300, Bruker Avance TM -400 or Bruker Avance TM -600 spectrometers. Mass spectra were recorded using Finnigan LCQ Advantage for ESI, on a Finnigan LTQ FT Ultra for HRMS (ICR) and Finnigan Polaris Q for EI.…”