A second-generation ferrocene–iminosugar hybrid with improved fucosidase binding properties

Hottin, Audrey; Scandolera, Amandine; Duca, Laurent; Wright, D.W.; Davies, G.J.; Behr, Jean‐Bernard

doi:10.1016/j.bmcl.2016.02.017

Cited by 17 publications

(6 citation statements)

References 24 publications

(28 reference statements)

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“…Most recently, ferrocene‐related anticancer research is also focusing on ferrocene–chalcogeno‐triazole–sugar conjugates, membrane interactions of nitroarylferrocenes, PEGylated ferrocene radiosensitizers of cancer cells, tubulin‐binding ferrocene‐substituted 3,3′‐diindolylmethane, ferrocene‐modified phospholipids, ferrocene–iminosugar hybrids, ferrocene–N‐heterocyclic carbene–gold(I) complexes targeting antioxidant pathways, and dendrimer‐related strategies . In terms of drug delivery, an elegant approach was reported by Wang's group with pH‐responsive supramolecular vesicles based on water‐soluble pillar[6]arene and ferrocene derivatives …”

Section: Ferrocenes In Nanomedicinementioning

confidence: 99%

Why is Ferrocene so Exceptional?

2016

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The appearance of ferrocene in the middle of the 20th century has revolutionized organometallic chemistry and is now providing applications in areas as varied and sometimes initially unexpected as optical and redox devices, battery and other materials, sensing, catalysis, including asymmetric and enantioselective catalysis, and medicine. The author presents here a general, although personal, view of ferrocene's chemistry, properties, functions, and applications through a literature survey involving both historical and up‐to‐date trends and including examples of his group's research in a number of these areas. The review gathers together general features of ferrocene chemistry and representative examples of the salient aspects. Its focus is on ferrocene's basic properties, ferrocene‐containing ligands, the ferrocene/ferricinium redox couple, ferrocene mixed‐valence and average‐valence systems, the ferricinium/ferrocene redox shuttle in catalysis, ligand‐exchange reactions, ferrocene‐containing polymers, ferrocene‐containing structures for cathodic battery and other materials, ferrocenes in supramolecular ensembles, liquid crystals, and nonlinear optical materials, ferrocene‐containing stars and their electrostatic effects, ferrocene‐containing dendrons, dendrimers, and nanoparticles (NPs) and their application in redox sensing and catalysis, and ferrocenes in nanomedicine.

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Section: Ferrocenes In Nanomedicinementioning

confidence: 99%

Why is Ferrocene so Exceptional?

2016

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“…Hottin et al extended the initial investigation and synthesized ferrocene analogue 45, with a triazole linker between pyrrolidine and ferrocene motif to improve the antifucosidase and anticancer activity against MDA-MB-231 and SK-MEL28 (human melanoma) cells (Figure 11). 35 Fucosidase was derived from bovine kidney and Bacteroides thetaiotaomicron. Interestingly, replacing the aryl ring with ferrocene improved the antifucosidase activity of 45 with K i value 23 and 150 nM against fucosidase and the thetaiotaomicron, respectively.…”

Section: Effect Of Amalgamation Of Ferrocene Onmentioning

confidence: 99%

Has Ferrocene Really Delivered Its Role in Accentuating the Bioactivity of Organic Scaffolds?

Sharma

Kumar

2021

J. Med. Chem.

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Ferrocene is an important structural core in bioorganometallic chemistry because of its inherent stability, excellent redox properties, and low toxicity. Ferroquine and ferrocifen are two of the most notable contributions of ferrocene to medicinal chemistry with remarkable antimalarial and anticancer properties. The improved medicinal properties of these drug candidates highlight the impact that ferrocene can have on the molecular and biological properties of the bioactive compounds. In this Perspective, we investigate the scope and limitations of ferrocene incorporation into organic compounds/natural products on their mode of action and biological activities. We have also discussed the detailed role of ferrocene modifications in influencing the anticancer, antimalarial, and antimicrobial properties of various bioactive moieties to design safer and promising ferrocene-based drugs.

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“…Employing Route C for the synthesis of 5-iodotriazoles is explained by the known fact that 5-iodotriazoles can be formed as byproducts in the CuAAC of terminal alkynes with azides even in the presence of a catalytic amount of CuI and an amine ligand. 51,52 This process, in particular, should be monitored in the synthesis of drugs, as illustrated in the case of solithromycin (Solithera ® ). 53 Currently Routes A and B are the most useful tools for the construction of 5-iodotriazoles due to the simplicity of the procedures, accessibility of the starting materials, and their tolerance to various functional groups.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks

Danilkina

Govdi²,

Балова³

2020

Synthesis

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Copper-catalyzed azide–alkyne cycloaddition is a useful tool for the synthesis of both 1,2,3-triazoles and 5-iodo-1H-1,2,3-triazoles starting from either terminal alkynes or iodoalkynes. 5-Iodotriazoles have been recognized as very useful building blocks for the synthesis of diverse 1,4,5-trisubstituted 1,2,3-triazoles. Synthetic application of 5-iodo-1,2,3-triazoles through the creation of a new C–C, C–heteroatom, or C–D(T) bond along with the application areas of both iodotriazoles and products of their modification including radiolabeled compounds are discussed.1 Introduction2 Synthetic Approaches to 5-Iodo-1H-1,2,3-triazoles3 5-Iodotriazoles in C–C Bond Formation3.1 Intermolecular C–C Cross-Coupling3.2 Intramolecular Cross-Coupling: Direct Arylation and C–I/C–I Homocoupling3.3 Other Transformations4 5-Iodotriazoles in Radiolabeling, Halogen Exchange, and Heterocoupling Reactions5 Summary

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A second-generation ferrocene–iminosugar hybrid with improved fucosidase binding properties

Cited by 17 publications

References 24 publications

Why is Ferrocene so Exceptional?

Why is Ferrocene so Exceptional?

Has Ferrocene Really Delivered Its Role in Accentuating the Bioactivity of Organic Scaffolds?

5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks

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