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3,3'-DIINDOLYLMETHANES - SYNTESIS AND STRUCTURAL ANALYSIS

Magdalena Rasztawicka ,  Dorota Maciejewska 

Medical University of Warsaw, Faculty of Pharmacy, Department of Organic Chemistry (AM), Banacha 1, Warszawa 02-097, Poland

Abstract

3,3'-Diindolylmethane is a promising cancer chemopreventive agent derived from Brassica food plants, and its mode of action is widely examined. Therefore we have chosen it as a template structure in our search for new compounds with better pharmacological profile.

In course of our studies we are interested in optimization of synthetic procedure leading to 5,5'- or 6,6'-disubstituted bis-indoles (Fig. 1) [1].

magda1_3.PNG

Fig. 1. Intermediates in the synthesis of bis-indoles.

The 1H and 13C NMR spectra of reagents in solution show standard resonances and enabled us to confirm the synthetic pathway.

The 13C CP/MAS NMR spectra of products represent various signal patterns. This could have been caused by:

- the presence of two energetically similar conformers in the solid state

- the different packing mode of both indole rings in one conformer

- the presence of only one conformer with magnetically equivalent C atoms in both indole rings

1. D. Maciejewska, M. Niemyjska, I. Wolska, M. Włostowski, M. Rasztawicka in Z. Naturforsch. 59b, 1137-1142, (2004).

 

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Submitted: 2006-01-19 11:05
Revised:   2009-06-07 00:44