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Synthesis new 1,2,4-triazoline- and 1,3,4-tiadiazole - isoxazole derivatives with immunomodulatory activities

Marcin Mączyński 1Michał Zimecki 2Stanisław Ryng 1

1. Wrocław Medical University, Faculty of Pharmacy, Department of Organic Chemistry, Grodzka 9, Wrocław 50-137, Poland
2. Polish Academy of Sciences, Institute of Immunology and Experimental Therapy (IITD), Rudolfa Weigla 12, Wrocław 53-114, Poland

Abstract

Intensive studies on new, biologically active isoxazole derivatives, have been conducted for the last few decades. We synthesized a group of monocyclic and bicyclic isoxazole derivatives. In the group of monocyclic compounds, the pharmacophore structure was a fragment of 5-amino-3-methyl-4-isoxazolecarboxylic acid. The importance of the pharmacophore structure of 5-amino-3-methylo-4-isoxazolecarboxylic acid, contained in N'-substituted hydrazides, semicarbazides, semithiocarbazides of that acid with immunosupressory activities and isoxazoleoxadiazol, isoxazolopirazol and isoxazolopirol, with high immunomodulatory activities, was confirmed in several patents.

Looking for active immunomodulators we synthesized new 4-substituted 3-(5-amino-3-methyl-4-isoxazole)-1,2,4,-triazoline-5-tione and 5-substituted 2-(5-amino-3-methyl-4-isoxazole)-1,3,4-tiadiazole derivatives. We obtained the compounds in reaction of 5-amino-3-methyl-4-isoxazolecarboxylic acid thiosemicarbazides with conc. sulphuric acid or sodium hydroxide.

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Related papers

Presentation: Poster at VI Multidyscyplinarna Konferencja Nauki o Leku, by Marcin Mączyński
See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2008-03-12 11:23
Revised:   2009-06-07 00:48