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O ‐2′,3′‐Ketal‐Nucleolipids of the Cytostatic 5‐Fluorouridine: Synthesis, Lipophilicity, and Acidic Stability
Author(s) -
Malecki Edith,
Rosemeyer Helmut
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201000121
Subject(s) - lipophilicity , chemistry , ring (chemistry) , nuclear magnetic resonance spectroscopy , high performance liquid chromatography , stereochemistry , organic chemistry , combinatorial chemistry , medicinal chemistry
The synthesis of a series of cyclic and acyclic O ‐2′,3′‐ketal derivatives of the cancerostatic 5‐fluorouridine ( 2a ) is described. The novel compounds were characterized by 1 H‐ and 13 C‐NMR, and UV spectroscopy, as well as by elemental analyses. The lipophilicity values (log P , retention times in RP‐18 HPLC) of the cyclic ketals were determined and related to the ring tensions as well as the acid stability of the spiro‐linked ketal rings.