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Beilstein J Org Chem. 2010 Apr 12;6:34. doi: 10.3762/bjoc.6.34.

Symmetrical and unsymmetrical alpha,omega-nucleobase amide-conjugated systems.

Author information

  • 1Silesian University of Technology, Department of Organic Chemistry, Biochemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.

Abstract

We present the synthesis and selected physicochemical properties of several novel symmetrical and unsymmetrical alpha,omega-nucleobase mono- and bis-amide conjugated systems containing aliphatic, aromatic or saccharidic linkages. The final stage of the synthesis involves condensation of a subunit bearing carboxylic group with an amine subunit. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) was found to be a particularly effective condensing agent. The subunits containing carboxylic groups were obtained by acidic hydrolysis of N-1 Michael adducts of uracils or N-9 Michael adducts of 6-chloropurine with methyl acrylate. The amines used were aliphatic/aromatic diamines, adenine, 5-substituted 1-(ω-aminoalkyl)uracils and 5'-amino-2',5'-dideoxythymidine. The title compounds may find application as antiprotozoal agents. Moreover, preliminary microscopy TEM studies of supramolecular behaviour showed that target molecules with bolaamphiphilic structures were capable of forming highly ordered assemblies, mainly nanofibres.

KEYWORDS:

amides; antiprotozoal agents; coupling; nucleosides; self-assembly

PMID:
20502605
[PubMed]
PMCID:
PMC2874405
Free PMC Article

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