Synthesis, structure and enantiomeric resolution of ferrocenylalkyl mercaptoazoles. Antitumor activity in vivo

Rodionov, A.N.; Zherebker, K.Y.; Snegur, L.V.; Korlyukov, A.A.; Arhipov, D.E.; Peregudov, A.S.; Ilyin, M.M.; Jr; Nikitin, O.M.; Morozova, N.B.; Simenel, A.A.

Авторы: Rodionov A.N., Zherebker K.Y., Snegur L.V., Korlyukov A.A., Arhipov D.E., Peregudov A.S., Ilyin M.M., Jr, Nikitin O.M., Morozova N.B., Simenel A.A.
Журнал: Journal of Organometallic Chemistry
Том: 783
Год издания: 2015
Издательство: Elsevier BV
Местоположение издательства: Netherlands
Первая страница: 83
Последняя страница: 91
DOI: 10.1016/j.jorganchem.2015.01.031
Аннотация: Ferrocenylalkyl 2-mercaptobenzimidazoles 3 (a-e) and 2-mercaptobenzo[d]thiazole-2(3H)-thiones 5 (a-e) were prepared via the reaction of the α-(hydroxy)alkyl ferrocenes, FcCHR(OH) (1a-e; Fc = ferrocenyl; R = H, Me, Et, i-Pr, Ph), either with thiobenzimidazole in acetone at room temperature in the presence of TFA (catalytic amounts), in yields of 55-74%, or with thiobenzothiazole in methylendicloride in presence of aqueous HBF4 (equimolar amounts) at r.t.; in yields of 41-58%. The structures, electrochemical properties and enantiomeric resolution 3a-e and 5a-e (using HPLC on modified amylose as chiral selector) were investigated. In cyclic voltammetry all studied compounds exhibited a reversible one-electron oxidation-reduction wave owing to the ferrocene-ferricenium redox couple with a positive shift (0.56-0.80 V) compared with that of ferrocene (0.50 V). X-ray determinations of molecular structures of 3-ferrocenylmethylbenzo[d]thiazole-2(3H)-thione (5a) 3-ferrocenylethylbenzo[d]thiazole-2(3H)-thione (5b) and 3-ferrocenylphenylmethylbenzo[d]thiazole-2(3H)-thione (5d) were carried out. The toxicity and antitumor activity of N-(ferrocenylethyl)-2-thiobenzimidazole (3b) were evaluated in vivo. Maximum tolerated dose (MTD) value for the compound 3b was found to be equal to 800 mg kg-1. The effectiveness of compound under investigation against murine solid tumor system, carcinoma Ca755 (Ca755), was studied in a wide range of doses and significant antitumor effects were found. The index of tumor growth inhibition (TGI) on Ca755 equaled 87% in comparison with control.
Добавил в систему: Никитин Олег Михайлович

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Synthesis, structure and enantiomeric resolution of ferrocenylalkyl mercaptoazoles. Antitumor activity in vivoстатья

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