Naslov
Spontaneous resolution of N-sulfonylpyrimidine compounds induced by chemical modifications

Autori
Višnjevac, Aleksandar ; Luić, Marija, Žinić, Mladen ; Žinić, Biserka

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
XX Congress of the International Union of Crystallography, Book of Abstracts ; Acta Crystallographica A61 / Mealli, Carlo ; Paoli, Paola - Firenza : München : International Union of Crystallography, 2005, C365-C365

Skup
XX Congress of the International Union of Crystallography

Mjesto i datum
Firenca, Italija, 23.08.2005. - 31.08.2005

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Conformational Chirality; Racemic Twinning; Pyrimidine Nucleobases

Sažetak
The title compounds belong to a novel series of pyrimidine nucleobase derivatives, some of which exhibit significant anticancer activity in vitro.[1] The crystal structures of 1-tosylthymine (1), 1-tosyluracil (2),  -naphthyl derivatives of thymine (3) and uracil (4) are presented. The conformational chirality was encountered in all compounds, as the consequence of the S-N single bond free rotation hindrance in solid state (atropisomerism).[2] The spontaneous resolution (á la Pasteur) of P and M conformational enantiomers occurred during the crystallization of 2 and 4, whereas their 5-methyl analogues, 1 and 3, crystallized as racemic mixtures. Moreover, spontaneous resolution in the case of 2 was accompanied by a formation of racemically twinned crystals regardless of the solvent used. Obviously, substituents at C-5 position of pyrimidine base as well as in -SO2-R group dictate the occurrence (or absence) of spontaneous resolution. [1] Ruđer Bošković Institute (B. Žinić, M. Žinić, I. Krizmanić) EP 0 877 022, 2003. [2] I.D. Cunningham, S.J. Cooles, M.B. Hursthouse, Chem. Comm. (2000) 61-62.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA