Zaitsev, Kirill V., Trubachev, Andrei D., Antonenko, Taisiya A., Gracheva, Yulia A., Zazdravnykh, Anastasiya V., Milaeva, Elena R., Oprunenko, Yuri F., and Lermontova, Elmira Kh.
A series of substituted bis(triazole) derivatives of organodigermanes (1–3) containing reactive phenolic and sugar functional groups, [1,4-C2HN3(R)GePh2–]2(R = β-(d)-glucopyranoso-C5H5O(OAc)3CH2OAc (1); R = CH2–1,2,3,5-(HO)C6H2(t-Bu)2(2); and R = CH2–1,2,3,5-(HO)C6H2(CHO)(t-Bu) (3)), was synthesized by the copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction. The structural features (1, XRD analysis) and optical properties (1–3, absorbance, and emission) of these digermanium heterocyclic compounds were studied. The antioxidant (DPPH test), lipoxygenase inhibitory (inhibition of LOX 1-B), and antiproliferative activities (MTT test; HCT-116, MCF-7, A-549 cancer cell lines) of differently substituted 1–6(R = p-BrC6H4CH2(4); R = CH2COOEt (5); R = CH2CH2O-p-C6H4CHO (6)) were investigated, indicating their promising antioxidant (for 2EC50103 ± 4 μM) and lipoxygenase inhibition activity (for 4IC5029 ± 2 μM), moderate antiproliferative activities (for 5IC5055–71 μM), and low toxic properties (WI-38, IC50> 36 μM). Comparison of the biological activity of the leader digermanes 2, 4, and 5with related organic triazoles 1,4-C2HN3(R) (2a, 4a, 5a) and monogermanes 1,4-C2HN3(R)GePh3(2b, 4b, and 5b) indicates the influence of the Ge–Ge fragment.