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Ferrocene‐modified thiopyrimidines: synthesis, enantiomeric resolution, antitumor activity
Author(s) -
Simenel Alexander A.,
Dokuchaeva Galina A.,
Snegur Lubov' V.,
Rodionov Alexey N.,
Ilyin Mikhail M.,
Zykova Svetlana I.,
Ostrovskaya Larissa A.,
Bluchterova Natalia V.,
Fomina Margarita M.,
Rikova Valentina A.
Publication year - 2011
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.1691
Subject(s) - chemistry , lewis lung carcinoma , enantiomer , in vivo , alkyl , acetone , stereochemistry , ferrocene , organic chemistry , cancer , medicine , microbiology and biotechnology , electrode , electrochemistry , biology , metastasis
Ferrocenylalkyl thiopyrimidines ( 6a–d to 9a–d ) were prepared via the reaction of the α‐(hydroxy)alkyl ferrocenes, FcCHR(OH) ( 1a–d ; Fc = ferrocenyl; R = H, Me, Et, Ph), with 2‐thiopyrimidines ( 2 – 5 ) in acetone at room temperature in the presence of TFA, yielding 50–95%. The resulting enantiomers were resolved using HPLC on modified cellulose as chiral selector. The antitumor activities of S ‐ferrocenylethyl 2‐thiopyrimidine ( 6b ) against two murine solid tumor models, carcinoma 755 (Ca755) and Lewis lung carcinoma (LLC) were evaluated in vivo . The strong antitumor effect of compound 6b on Ca755 and LLC was demonstrated. The index of tumor growth inhibition on Ca755 equaled 95% in comparison with control. Copyright © 2010 John Wiley & Sons, Ltd.