Synthesis, characterization, and pharmacological studies of ferrocene-1H-1,2,3-triazole hybrids

Abstract

A series of ferrocene-1H-1,2,3-triazole hybrids namely 1-(4-nitrophenyl)-4-ferrocenyl-1H-1,2,3-triazole (1), 1-(4,4'-dinitro-2-biphenyl)-4-ferrocenyl-1H-1,2,3-triazole (2), 1-(3-chloro-4-fluorophenyl)-4ferrocenyl-1H-1,2,3-triazole (3), 1-(4-bromopheny1)-4-ferroceny1-1H-1,2,3-triazole (4) and 1-(2nitrophenyl)-4-ferrocenyl-IH-1,2,3-triazole (5) were designed and synthesized by copper-catalyzed azide alkyne cycloaddition (CuAAC) reaction. All the new hybrids were characterized by microanalyses, NMR (H-1 and C-13), UV-vis, IR, ESI-MS and electrochemical techniques. Crystal structure of the compound (3) was solved by single crystal X-ray diffraction method. The structural (single crystal) and spectroscopic (UV Vis. and IR) properties of the compound 3 have been analyzed and compared by complementary quantum modeling. Hybrids 1-5 exhibited low toxicity and demonstrated neuroprotective effect. (C) 2017 Elsevier B.V. All rights reserved.