1277-77-6

Upstream product

• 13292-87-0 dimethyl sulfide borane 
• 766-77-8 Dimethylphenylsilane 
• 102-54-5 ferrocene 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 152196-81-1 4-(ferrocenylmethyl)phenol 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of novel hybrid ferrocenyl compounds based on a bicyclic core skeleton for breast cancer therapy

Breast cancer is the most frequent cancer in women worldwide, and incidence is increasing year by year. Although current selective estrogen receptor modulators (SERMs) have clear advantages in the treatment of hormone-responsive breast cancer, they are ineffective for ER(-). In this study, we describe the design and synthesis of a series of dual-acting estrogen receptor (ER) and histone deacetylase (HDAC) inhibitors with incorporation of the ferrocenyl moiety, leading to novel hybrid ferrocenyl complexes (FcOBHS-HDACis) for breast cancer therapy. It is worth to note that these ferrocenyl conjugates could not only potently inhibit HDACs and the proliferation of ERα positive (ER(+)) breast cancer cells (MCF-7), but also show significant antiproliferative effect on ER(-) breast cancer cells (MDA-MB-231). Thus, the FcOBHS-HDACi conjugates represent a novel approach to the development of efficiently dual-acting agents for treatment of breast cancer.

Discovery of novel SERMs with a ferrocenyl entity based on the oxabicyclo[2.2.1]heptene scaffold and evaluation of their antiproliferative effects in breast cancer cells

We have synthesized a series of novel SERMs bearing a ferrocenyl unit based on a three-dimensional oxabicyclo[2.2.1]heptene core scaffold. These compounds displayed high receptor binding affinities as well as ERα or ERβ selectivity. In cell proliferation

Highly efficient reduction of ferrocenyl derivatives by borane

Borane, as a DMS or a THF complex, can efficiently reduce a large range of ferrocenyl derivatives (aldehydes, ketones, ethers, acetals, carboxylic acids, esters,...) if they bear at least one oxygen at a carbon at the α position. On the contrary, similar molecules, which contain nitrogen instead of oxygen, do not react with borane.

Oxidation potential of benzylferrocenes and related compounds: Effects of the ortho-methoxy substituent in the phenyl group

Oxidation potentials of some ferrocenyl derivatives of type Fc-CHΦOH, Fc-CΦΦ′OH, Fc-CH2Φ, Fc-CHΦΦ′ [Fc=Fe(η5-C5H5)(η5-C 5H4); Φ, Φ′=2,4,6-(MeO)3C6H2, 2,6-(MeO)2·C6H3, 2,5-(MeO)2·C6H3, 2,4-(MeO)2·C6H3, 2-MeOC6H4, 4-MeOC6H4, C6H5] were measured in acetonitrile. All of them exhibited a reversible one-electron oxidation-reduction wave based on the ferrocene-ferrocenium redox couple with a wide range of shift. Compounds having ortho-methoxy groups showed lower redox potentials than those of compounds having para-methoxy groups. The X-ray crystal structure of Fc-CHΦ2a showed that the ortho-methoxy oxygens were situated very close to the central carbon, and there is a possibility that one of the oxygen lone-pairs interacts with the antibonding orbital of C-Fc σ-bond. Some other possibilities are also discussed.

How Electrophilic are Ferrocenylmethyl Cations? Kinetics of their Reactions with ? Nucleophiles and Hydride Donors

Second-order rate constants for the reactions of the ferrocenylmethylium ions 2a-e with silyl enol ethers, allylsilanes, allylstannanes, and hydride donors have been determined photometrically and conductometrically in dichloromethane.The ferrocenylmethylium ions 2a-d (fc-CHR(+), R = H, Me, Ph, An) are slightly stronger electrophiles than the tropylium ion, and their electrophilic reactivities depend only slightly on the nature of R.The bis(ferrocenyl)methylium ion 2e is a considerably weaker electrophile, comparable to the tricarbonyl(cyclohexadienyl)iron cation. - Key Words: Electrophilicity / Ferrocenylmethylium ions / Kinetics