THE NEW WATER SOLUBLE SALTS, PRONE TO SPONTANEOUS DECOMPOSITION WITH FORMATION OF 2-CHLOROETHYLAMINO MOIETY (NITROGEN MUSTARD DERIVATIVES)

Zbigniew J. Kamiński 1Beata Kolesińska 1Karolina Wąsikowska 1Konrad Jastrząbek 1Danuta Drozdowska 2

1. Technical University of Łódź, Institute of Organic Chemistry (PŁ), Żeromskiego 116, Łódź 90-924, Poland
2. Medical University, Department of Organic Chemistry, Mickiewicza 2A, Białystok 15-222, Poland

Abstract

The variety of compounds with 2-chloroethylamino fragment (nitrogen mustard analogues) with strong alkylating activity terminate the proliferation of the cells, however, due to the strong toxic and mutagenic side-effects, their therapeutic value is substantially limited. Therefore, the search is provided for the non-alkylating precursors prone to conversion under physiological conditions with formation of the mustard moiety, as potential pro-drugs for the cancer therapy.

Recently, we found that some N-triazinylammonium chlorides 3 easy accessible from broad range of triazines 1 and 1,4-diazabicyclo[2.2.2]octane (DABCO) (2) rearranged with a formation of 4 bearing 2-chloroethylamino fragment.

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The most of N-triazinylammonium salts 3 were obtained in almost quantitative yield. Rearrangement of 3 to 4 proceeds spontaneously at room temperature slowly and is accelerated in non-aqueous media and at elevated temperatures. Both 3 and 4 were isolated and identified. Compounds 4 were investigated in the standard cell line of mammalian tumor MCF-7.

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Presentation: Poster at V Multidyscyplinarna Konferencja Nauki o Leku, by Zbigniew J. Kamiński
See On-line Journal of V Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2006-01-31 20:07
Revised:   2009-06-07 00:44
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