Original scientific paper

New Acyclic Purine Nucleoside Analogues Containing Exocyclic Pyrrolo Moiety: Synthetic, NMR and X-ray Crystal Structure Studies

Silvana Raić ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, 10000 Zagreb, Croatia
Mario Pongračić ; Pliva Research Institute, Prilaz baruna Filipovića 25, 10000 Zagreb, Croatia
Jasna Vorkapić-Furač ; Faculty of Food Technology and Biotechnology, University of Zagreb, 10000 Zagreb, Croatia
Dražen Vikić-Topić ; Ruder Bošković Institute, Laboratory of Molecular Spectroscopy, Bijenička 54, 10000 Zagreb, Croatia
Antonija Hergold-Brundić ; Laboratory of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Zvonimirova 8, 10000 Zagreb, Croatia.
Ante Nagl ; Laboratory of General and Inorganic Chemistry, Faculty of Science, University of Zagreb, Zvonimirova 8, 10000 Zagreb, Croatia.
Mladen Mintas ; Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 20, 10000 Zagreb, Croatia

Abstract

The synthesis of novel 6-(N-pyrrolyl)purine nucleoside analogues
containing acyclic side chains attached to the purine ring at N-9 is
described. The structures were determined by 1H and 13CNMR on
the basis of chemical shifts, substituent induced shifts, C-H coupling
constants and connectivity in the COSY,NOESY and HETCOR spectra. Unequivocal proof for the stereostructure of 6 was obtained by its X-ray crystallographic analysis. Geometrical data from X-ray structural analysis showed that the two 6-(N-pyrrolyl) purine rings involved in the skeleton of 6 are anti-disposed but not centrosymmetric with respect to the central aliphatic bridge.

Keywords

Hrčak ID:

177125

URI

https://hrcak.srce.hr/177125

Publication date:

1.11.1996.

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