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Ferrocene‐Modified Purines as Potential Electrochemical Markers: Synthesis, Crystal Structures, Electrochemistry and Cytostatic Activity of (Ferrocenylethynyl)‐ and (Ferrocenylethyl)purines
Author(s) -
Hocek Michal,
Štěpnička Petr,
Ludvík Jiří,
Císařová Ivana,
Votruba Ivan,
Řeha David,
Hobza Pavel
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305621
Subject(s) - purine metabolism , cyclic voltammetry , electrochemistry , chemistry , ferrocene , sonogashira coupling , platinum , palladium , catalysis , crystal structure , medicinal chemistry , inorganic chemistry , stereochemistry , combinatorial chemistry , organic chemistry , electrode , enzyme
Abstract Palladium‐catalyzed Sonogashira cross‐coupling reactions of halopurines 9‐benzyl‐6‐chloropurine ( 2 a ), 9‐benzyl‐8‐bromoadenine ( 2 b ), and 9‐benzyl‐2‐chloroadenine ( 2 c ) with ethynylferrocene ( 1 ) gave the corresponding (ferrocenylethynyl)purines 3 a–c in moderate to good yields. Catalytic hydrogenation of these alkynes over Pd/C afforded the respective saturated [2‐(ferrocenyl)ethyl]purines 4 a–c . The crystal structures 3 a , 3 b , 4 a and 4 b as determined by X‐ray diffraction show interesting solid‐state interactions, markedly different for purines 3 a and 4 a on one hand and adenines 3 b and 4 b that possess a free amino group on the other. Electrochemistry of electrochemically labelled purines 3 and 4 has been studied by voltammetry and cyclic voltammetry on platinum disc electrode and the experimental oxidation potentials were confirmed and explained by ionization potentials from theoretical DFT calculations. Several compounds of this series exhibited a considerable cytostatic effect.