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Conformation and supramolecular interactions in O-alkylated quinoline and ferrocene conjugates

Ferrocenes conjugated with biologically active heterocycles have been found to exhibit promising cytostatic effects, such as, carbohydrate ferrocene conjugates with amide or triazole linker were effective on some hormone‐dependent and hormone-independent cancer cells lines [1]. Besides, quinoline derivatives containing additional aromatic rings have been reported to possess potent anticancer activities [2]. In this contribution, we present supramolecular structures and conformation of three O-alkylated quinoline and ferrocene conjugates (Fig. 1). Cyclopentadienyl rings in 2 and 3 deviate only slightly from an eclipsed conformation, while in 1 it is almost halfway between eclipsed and staggered. In supramolecular structures dominate dimer motif formed by C-H···N or/and C-H···F hydrogen bonds. Their combination forms chain of rings, like in 2 (Fig. 2), while the C-H···Pi or/and Pi···Pi interactions extend this motif into three-dimensional or two-dimensional network. References: [1] Deepthi, S.B., Trivedi, R., Giribabu, L., Sujitha, P. & Kumar, C.G. (2013) Dalton Trans. 42, 1180-1190. [2] de Freitas, L.B., Borgati, T.F., de Freitas, R.P., Ruiz, A.L.T.G., Marchetti, G.M., de Carvalho, J.E., da Cunha, E.F.F., Ramalho, T.C. & Alves, R.B. (2014) Eur. J. Med. Chem. 84, 595-604.

ferrocene skeleton, quinoline ring, conformation, supramolecular assembling

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