Ferrocene‐modified thiopyrimidines: synthesis, enantiomeric resolution, antitumor activity

The synthesis, structure, electrochemistry and in vitro anticancer activity studies of ferrocenyl-thymine conjugates

“…The in vivo antitumor activities against selected animal tumor systems such as carcinoma 755, melanoma B16 and Lewis lung carcinoma of N-ferrocenylmethyl thymine 8 (Fig. 1) and ferrocenyl-thiopyrimidines were reported recently [31,32]. Also ferrocenyl-thymine 9 and ferrocenyl-adenine 10, which were recently obtained by a "click chemistry" approach, have been tested for their antioxidant activities [33].…”

Enantiomeric-Enriched Ferrocenes: Synthesis, Chiral Resolution, and Mathematic Evaluation of CD-chiral Selector Energies with Ferrocene-Conjugates

“…The stabilization of the carbocation center by electron-rich ferrocene fragment governs the stereoselectivity of the reactions. This effective strategy has been previously applied for the synthesis of racemic Fc-azoles and Fc-nucleic bases [ 15 , 18 , 22 , 32 , 35 , 53 ].…”

“…In this paper, the development of our ferrocene-devoted works [ 31 , 32 , 33 , 34 , 35 , 36 ] are reported. We proposed a simple route to enantiomeric-enriched ferrocene-based compounds.…”

Ferrocenes as potential anticancer drugs. Facts and hypotheses

“…All compounds studied were found to possess moderate or low toxicities: LD 50 for them are in the range of 180-1500 mg kg -1 (see Refs 14,51,52,55,and 127).…”

“…127 Some compounds, for example, ferrocenylethyl 2 thiopyrimidine, possess a prolonged action and their growth inhibiting effect remains at the level of 40-80% for 9-13 days after completion of drug administration. 51 Yet another trend in the search of potential bioactive ferrocene derivatives is related to the synthesis of plati num(II) and some other metal complexes with mono and bidentate ferrocene containing ligands. 117-119,124,129, 130 In particular, it was found in the study of cytotoxicity of bis(diphenylphosphino)ferrocene and its complex with ruthenium(III) nitrosyl chloride against the breast cancer cell culture (MDA MB 231 line) that the cytotoxicity of bis(diphenylphosphino)ferrocene (IC 50 = 97 mol L -1 ) increases almost by an order of magnitude upon coordina tion to the inactive nitrosylruthenium trichloride (IC 50 of the complex is 10 mol L -1 ).…”