Organodigermanium Compounds: Structures and Properties

Abstract

A series of substituted bis(triazole) derivatives of organodigermanes (1−3) containing reactive phenolic and sugar functional groups, [1,4-C 2 HN 3 (R)GePh 2 −] 2 (R = β-(D)-glucopyranoso-C 5 H 5 O(OAc) 3 CH 2 OAc (1); R = CH 2 −1,2,3,5-(HO)C 6 H 2 (t-Bu) 2 (2); and R = CH 2 −1,2,3,5-(HO)C 6 H 2 (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-BrC 6 H 4 CH 2 (4); R = CH 2 COOEt (5); R = CH 2 CH 2 O-p-C 6 H 4 CHO (6)) were investigated, indicating their promising antioxidant (for 2 EC 50 103 ± 4 μM) and lipoxygenase inhibition activity (for 4 IC 50 29 ± 2 μM), moderate antiproliferative activities (for 5 IC 50 55−71 μM), and low toxic properties (WI-38, IC 50 > 36 μM). Comparison of the biological activity of the leader digermanes 2, 4, and 5 with related organic triazoles 1,4-C 2 HN 3 (R) (2a, 4a, 5a) and monogermanes 1,4-C 2 HN 3 (R)GePh 3 (2b, 4b, and 5b) indicates the influence of the Ge−Ge fragment.