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Updated: Jun 20, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
Published on: May 28, 2014
Different routes for amination of platinum(II)-bound cyanoguanidine
Alexander G Tskhovrebov1, Nadezhda A Bokach, Matti Haukka
1Department of Chemistry, St. Petersburg State University, Univeritetsky Pr. 26, 198504 Stary Petergof, Russian Federation.
Abstract:
The consecutive addition of AgSO(3)CF(3) (1 or 2 equiv) and cyanoguanidine (1 or 2 equiv, respectively) to the platinum(II) precursor [PtI(2)(tmeda)] leads to the cis-[PtI(tmeda){NCN=C(NH(2))(2)}](SO(3)CF(3)) (1.(SO(3)CF(3))) or cis-[Pt(tmeda){NCN=C(NH(2))(2)}(2)](SO(3)CF(3))(2) (2.(SO(3)CF(3))(2)) complexes. The reaction between 1.(SO(3)CF(3)) or 2.(SO(3)CF(3))(2) and the excess of R(2)NH (R = H, R(2) = C(5)H(10)) in EtOH gives the triazapentadiene compounds cis-[Pt(tmeda){NHC(NR(2))NC(NH(2))NH}](SO(3)CF(3)) (3.(SO(3)CF(3)) and 4.(SO(3)CF(3)), correspondingly). Protonation of these species results in cis-[Pt(tmeda){NHC(NR(2))NHC(NH(2))NH}](SO(3)CF(3))(2) ([3.H](SO(3)CF(3))(2) and [4.H](SO(3)CF(3))(2), respectively). The interaction of solid 2.(SO(3)CF(3))(2) and the gaseous RNH(2) (R = H, Me) leads to cis-[Pt(tmeda){NHC(NHR)NHC(NH(2))NH}(2)](SO(3)CF(3))(2) (5.(SO(3)CF(3))(2) and 6.(SO(3)CF(3))(2), respectively). Treatment of an acetone solution of 2.(SO(3)CF(3))(2) with an aqueous NH(3) or the reaction of 5.(SO(3)CF(3))(2) with Me(2)CO produces the triazine complex cis-{Pt(tmeda){NH=CNHC(Me)(2)}NHC(NH)(2)N}(2)(SO(3)CF(3))(2) (7.(SO(3)CF(3))(2)). The reaction of 5.(SO(3)CF(3))(2) with Me(2)CO also leads to 7.(SO(3)CF(3))(2). All new complexes were characterized by elemental analyses (C, H, N), electrospray ionization mass spectrometry, IR, and (1)H and (13)C NMR spectroscopies. The structures of 1.(SO(3)CF(3)), 2.(SO(3)CF(3))(2), 3.(SO(3)CF(3)), [4.H](SO(3)CF(3))(2), 5.(SO(3)CF(3))(2), and 7.(SO(3)CF(3))(2) were determined by single-crystal X-ray diffraction.
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