2,4‐Thiazolidinedione as a Bioactive Linker for Ferrocenyl Sugar–Triazole Conjugates: Synthesis, Characterization and Biological Properties

Abstract

A new series of ferrocenyl sugar-triazole conjugates, derived from D-xylose, D-ribose and D-galactose, linked by a 2,4thiazolidinedione moiety, has been prepared. Facile 1,3-dipolar-Huisgen coupling reactions of the respective sugar azides with the ferrocenyl 2,4-thiazolidinedione alkyne units give the corresponding conjugates. These conjugates have been characterized by various spectroscopic techniques, including UV/Vis [a] Synthesis and CharacterizationThe compound 2,4-thiazolidinedione was prepared by a literature method [26] and was condensed with ferrocene-carboxaldehyde 1, under Knoevenagel conditions, to form compound 2, Scheme 1. Synthesis of ferrocenyl 2,4-thiaolidinedione alkyne.Scheme 2. Synthesis of ferrocenyl 2,4-thiazolidinedione sugar-triazole conjugates 5a-g.Eur. J. Inorg. Chem. 2018, 1571-1580 www.eurjic.org

Photoisomerization of Arylidene Heterocycles: Toward the Formation of Fused Heterocyclic Quinolines

“…To evaluate the efficiency of the photoinduced isomerization, the stereochemistry of these arylidene heterocycles 1a–w , used as starting materials, was a crucial element and needed a careful investigation. Based on the literature ,− and our own recent works, the stereochemistry was defined as pure ( Z ) for the Ar-TZD derivatives 1a–f , h–m and pure ( E ) for the arylidenepyrrolidine-2,5-diones 1g , n , o . Our hypothesis was confirmed by X-ray diffraction performed on 2- or 3-nitro-benzylidenethiazolidine-2,4-diones 1i or 1j (Figure and Supporting Information section 1) and by 1 H NMR NOESY experiment for 1n and 1w (for details, see Supporting Information section 2).…”

1,2,3‐Triazole derivatives of 3‐ferrocenylidene‐2‐oxindole: Synthesis, characterization, electrochemical and antimicrobial evaluation

“…Structural motifs containing ferrocene‐triazoles and carbohydrate‐triazoles are known for their cytotoxicity and antimicrobial activities . Recently, our group has also reported on the biological properties of imidazolinones‐ and thiazolidinediones‐linked ferrocene derivatives . In continuation of these studies, herein, we describe the synthesis, electrochemical as well as antimicrobial activity of a series of different ferrocenyl triazole conjugates linked via oxindole moiety.…”

“…Ferrocifens, hydroxyferrocifens and the ferrocene analogue of anti‐androgen, nilutamide, are some of the well‐known ferrocene derivatives that exhibit significant cytotoxicity. The ferrocene analogue of the antimalarial drug chloroquine, ferroquine, has also been studied extensively . These examples have provided impetus for the study of different types of ferrocene conjugates for biological applications …”

Trithiolato-Bridged Dinuclear Arene Ruthenium(ll)- Glycoconjugates: Synthesis and Antiparasitic Activity

“…For example, this type of modification allowed the obtainment of RAPTA-type ruthenium(II)-arene anticancer compounds [81,99], but also the synthesis of various ligands used to generate carbohydratefunctionalized 1,2,3-triazolylidene ruthenium(II)-arene catalysts [44,45]. Likewise, various platinum, ruthenium and ferrocene glycoconjugates for bio-applications were obtained using click reactions [81][82][83][84][85]110]. Additionally, trithiolato diruthenium(II)-arene compounds suitably substituted with alkyne or azide groups were already used in CuAAC reactions for obtaining conjugates with molecules of interest e.g., various nucleic bases or drugs [95] .…”