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

Synthesis and anticancer activity studies of ferrocenyl-thymine-3,6-dihydro-2H-thiopyranes – A new class of metallocene-nucleobase derivatives

“…The synthesis of ferrocenyl-4-thiothymine-3,6-dihydro-2H-thiopyran 3 involved firstly the preparation of the thioketone 1 by a thionation reaction [18] between the ketone E [15] and Lawesson's reagent. This reaction afforded thioketone 1 as a blue solid in 77% yield.…”

“…To address this crucially important issue we have recently initiated a program in the synthetic chemistry of metallocenemodified nucleobases. We discovered that N1-regioselective Michael addition of the uracil group and in situ generated acryloylferrocene can serve as a new efficient method for the synthesis of a plethora of structurally diverse ferrocenyl-uracils [11,12,15]. As a continuation of our effort in the chemistry of metallocenemodified nucleobases, we describe in this communication the synthesis of two ferrocenyl-thymine-3,6-dihydro-2H-thiopyrane derivatives 3 and 4 (Scheme 1).…”

Purine and Purine Isostere Derivatives of Ferrocene: An Evaluation of ADME, Antitumor and Electrochemical Properties

“…It negatively regulates hypoxia-inducible factor-1α (HIF-1α) and showed to be effective under starved and hypoxic conditions frequently observed in advanced solid cancers. The anticancer potential of organometallic nucleoside analogues was explored [16][17][18] and showed that nucleoside analogues of ferrocene exhibited potent antineoplastic activity [19][20][21][22]. Combined application of ferrocenylalkyl nucleobase with anticancer drug cyclophosphamide demonstrated therapeutic synergism of antitumor activity against Lewis lung carcinoma (LLC) [23].…”

Synthesis and Characterization of Ferrocene Derivatives and Preliminarily Electrocatalytic Oxidation of L-Cysteine at Nafion-Ferrocene Derivatives Modified Glassy Carbon Electrode

“…Ferrocene derivatives have attracted considerable attention for their potential applications as nonlinear optical devices, functional materials in electrochemical sensor [1][2][3][4], and chiral catalysts [5][6][7]. In addition, ferrocene derivatives have also attracted wide interest for their considerably biological activities [8][9][10][11][12][13][14][15]. For example, the ferroquine (FQ, SSR97193, Figure 1) is about to complete phase II clinical trials as a treatment for uncomplicated malaria [16].…”