Dzolic, Zoran and Kristafor, Vedran and Cetina, Mario and Nagl, Ante and Hergold-Brundic, Antonija and Mrvos-Sermek, Draginja and Burgemeister, Thomas and Grdisa, Mira and Slade, Neda and Pavelic, Krešimir and Balzarini, Jan and De Clercq, Erik and Mintas, Mladen (2003) Synthesis, structural studies, and biological evaluation of some purine substituted 1-aminocyclopropane-1-carboxylic acids and 1-amino-1-hydroxymethylcyclopropanes. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 22 (4). pp. 373-389. ISSN 1525-7770, 1532-2335
Full text not available from this repository. (Request a copy)Abstract
The novel purine derivatives of 1-aminocyclopropane-1-carboxylic acid (8 and 9) and 1-amino-1-hydroxymethylcyclopropane (12 and 13) with methylene spacer between the base and the cyclopropane ring were prepared by multistep synthetic route involving alkylation of adenine and 6-(N-pyrrolyl)purine with 2-hydroxy-methyl-1-aminocyclopropane-1-carboxylic acid derivative 3 as a key reaction. All novel compounds were racemic. The N-9 substitution of the purine ring and the Z-configuration of the cyclopropane ring in 4-13 were deduced from their H-1 and C-13 NMR spectra by analyses of chemical shifts, H-H coupling constants and connectivities in two-dimensional homo- and heteronuclear correlation spectra. An unequivocal proof of the stereostructure of 1, 4 and 5 was obtained by their X-ray structure analysis. The novel compounds were evaluated on cytostatic and antiviral activities in several cell lines. The 6-(N-pyrrolyl)purine derivative of 1,2-aminocyclopropane alcohol 12 exhibited a more pronounced inhibitory activity against the proliferation of cervical carcinoma (HeLa) and human fibroblast (WI-38) cells than other types of tumor cell lines. None of the compounds showed inhibitory activities against cytomegalovirus, varicella-zoster virus or other viruses.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CARBOCYCLIC NUCLEOSIDES; ETHYLENE BIOSYNTHESIS; ACYCLIC NUCLEOSIDES; INHIBITORY ACTIVITY; ANTIVIRAL ACTIVITY; ANALOGS; NMR; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Central Analytical Services |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 26 Aug 2021 10:00 |
| Last Modified: | 26 Aug 2021 10:00 |
| URI: | https://pred.uni-regensburg.de/id/eprint/39511 |
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