Naslov
Synthesis, structural studies and biological evaluation of some purine substituted 1- aminocyclopropane-1-carboxylic acids and 1-amino-1-hydroxymethylcyclopropanes

Autori
Džolić, Zoran ; Krištafor, Vedran ; Cetina, Mario ; Nagl, Ante ; Hergold-Brundić, Antonija ; Mrvoš-Sermek, Draginja ; Burgemeister, Thomas ; Grdiša, Mira ; Slade, Neda ; Pavelić, Krešimir ; Balzarini, Jan ; De Clercq, Erik ; Mintas, Mladen

Izvornik
Nucleosides, nucleotides & nucleic acids (1525-7770) 22 (2003), 4; 373-389

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
1-aminocyclopropane-1-carboxylic acid derivatives ; cytostatic and antiviral activities ; single crystal x-ray analysis

Sažetak
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-hydroxymethyl-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 1H and 13C 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti

Napomena
Rad je objaljen i u ChemInform (0931-7597) 34 (2003) (43) ; https://onlinelibrary.wiley.com/doi/full/10.1002/chin.200343175 ; https://doi.org/10.1002/chin.200343175

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