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Conformational Chirality of Sulfonylpyrimidine Derivatives (CROSBI ID 497448)

Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija

Višnjevac, Aleksandar ; Luić, Marija ; Žinić, Mladen ; Žinić, Biserka Conformational Chirality of Sulfonylpyrimidine Derivatives // 22nd European Crystallographic Meeting : Book of Abstracts, Acta Cryst. A60 sxi / Mollnar, Istvan (ur.). Budimpešta: IUCr, 2004. str. 62-62-x

Podaci o odgovornosti

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

engleski

Conformational Chirality of Sulfonylpyrimidine Derivatives

The title compounds belong to a novel series of pyrimidine nucleobase derivatives possessing a sulfonamide pharmacophore. Some of them exhibit significant anticancer activity in vitro.[1] As the part of the overall structural examination, the crystal structures of 1-tosylthymine (1) and 1-tosyluracil (2) are presented. Both compounds crystallise in orthorhombic system (1 in Pbca and 2 in P212121), whereby the cell volume of 1 is twice as large as the one of 2 (doubling of one axis). The axial conformational chirality was encountered in both compounds, as the consequence of the S1-N1 single bond free rotation hindrance in solid state (atropisomerism). [2] The spontaneous resolution of Ra and Sa enantiomers occured only during the crystallisation of 2, whereas 1 crystallised as a racemate. Formation of chiral crystals of a compound without any stereogenic element is rare and of great interest in the field of absolute asymmetric synthesis in the solid state as well as in connection with the origin of homochirality of life. [3] The SHELXL merohedral twin refinement was applied in the case of the racemically twinned species (2), and the resulting Flack parameter was discussed. The interdependence of the crystal packing and the occurence of the spontaneous resolution was discussed, bearing in mind tiny chemical differences between 1 and 2. [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. [3] I. Azumaya, T. Kato, I. Okamoto, R. Yamasaki, A. Tanatani, K. Yamaguchi, H. Kagechika, H. Takayanagi, Org. Lett. (2003) 5, 3939-3942.

Conformational Chirality; Racemic Twinning; Pyrimidine Nucleobases

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Podaci o prilogu

62-62-x.

2004.

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objavljeno

Podaci o matičnoj publikaciji

22nd European Crystallographic Meeting : Book of Abstracts, Acta Cryst. A60 sxi

Mollnar, Istvan

Budimpešta: IUCr

Podaci o skupu

22nd European Crystallographic Meeting, ECM22

pozvano predavanje

26.08.2004-31.08.2004

Budimpešta, Mađarska

Povezanost rada

Kemija