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Ferrocenylalkyl azoles: bioactivity, synthesis, structure
Author(s) -
Snegur Lubov' V.,
Nekrasov Yury S.,
Sergeeva Nataliya S.,
Zhilina Zhanna V.,
Gumenyuk Vera V,
Starikova Zoya A.,
Simenel Alexander A.,
Morozova Nataliya B.,
Sviridova Irina K.,
Babin Valery N.
Publication year - 2008
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1362
Subject(s) - chemistry , ferrocene , aqueous solution , benzotriazole , iodide , solvent , stereochemistry , crystal structure , combinatorial chemistry , molecule , medicinal chemistry , organic chemistry , electrochemistry , electrode
The toxicity of ferrocenylethyl benzotriazole ( 1 ) and other ferrocene compounds including ferrocenylmethyl benzimidazoles ( 4,5,6,11 ), ferricenium salts ( 3,9,10 ) and ferrocenylmethyl adenine ( 7 ), was studied. All ferrocene complexes under investigation showed low or medium toxicities. On the basis of an earlier model of chemical carcinogenesis, the antitumor activity of ferrocenylalkyl azoles 1, 8 and ferricenium salts 9, 10 was studied in vivo in the so‐called sub‐capsular test on human tumors. This effectiveness was compared with that of cisplatin. A series of ferrocenylalkyl azoles were synthesized by interacting azoles either with α‐hydroxyalkyl ferrocenes FcC(OH)R 1 R 2 in organic solvent in the presence of aqueous HBF 4 in quantitative yields or with trimethyl(aminomethyl)ferrocene iodide in an aqueous‐basic medium in good yields. The X‐ray determinations of molecular and crystal structures of α‐(1‐benzotriazolyl)ethylferrocene ( 1 ) and α‐(1‐naphthatriazolyl)ethylferrocene ( 12 ) were performed. Copyright © 2008 John Wiley & Sons, Ltd.