Ferrocene‐modified thiopyrimidines: synthesis,enantiomeric resolution,antitumor activity |
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| Authors: | Alexander A. Simenel Galina A. Dokuchaeva Lubov' V. Snegur Alexey N. Rodionov Mikhail M. Ilyin Svetlana I. Zykova Larissa A. Ostrovskaya Natalia V. Bluchterova Margarita M. Fomina Valentina A. Rikova |
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| Affiliation: | 1. A. N. Nesmeyanov Institute of OrganoElement Compounds, Russian Academy of Sciences, 28 Vavilov St, 119991 Moscow, Russian Federation;2. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 Kosigin St, 119991 , Russian Federation |
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| Abstract: | 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. |
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| Keywords: | synthesis ferrocene α ‐(hydroxy)alkylferrocenes thiopyrimidines ferrocenylalkyl thiopyrimidines enantiomeric resolution HPLC antitumor activity |
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