1000073-56-2

Upstream product

• 33113-26-7 (C₅H₅)Fe(C₅H₄COC₆H₄OCH₃) 

Downstream Products

• 1000073-55-1 1,2-diferrocenyl-1-(3-hydroxyphenyl)-but-1-ene 

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.

Ferrocene oxo bridge bicyclo - [2.2.1] - heptylene class compounds

The invention discloses a ferrocene-bridged bicyclic-[2.2.1]-heptyl diene compound that contains N-hydroxy-(i)N-benzene succinic amide or a similar structure. 3-(4-hydroxyphenyl)-4-suberic nonacylanilino-furan or similar analogs and a ferrocene vinyl sulfonate derivative are used as raw materials, and a solvent and a catalyst are not needed; the raw materials are reacted for 3 hours at 90 DEG C through one step to obtain a ferrocene-bridged bicyclic-[2.2.1]-heptyl diene compound that contains a suberic nonacylanilino group. According to an in vitro experiment, compared with a current anti-cancer drug Tamoxifen, the novel ferrocene-bridged bicyclic-[2.2.1]-heptyl diene compound has stronger inhibitory activity on hormone-dependent breast cancer MCF-7 cells and non-hormone-dependent breast cancer MDA-MB-231 cells, and has no toxicity on normal VERO cells while the current anti-cancer drug Tamoxifen has toxicity on normal VERO cells.

The influence of phenolic hydroxy substitution on the electron transfer and anti-cancer properties of compounds based on the 2-ferrocenyl-1-phenyl-but-1- ene motif

The ferrocenyl compound 2-ferrocenyl-1,1-bis(4-hydroxyphenyl)-but-1-ene (3), is very cytotoxic against breast cancer cells (IC50 = 0.44 M against MDA-MB-231). We now report the synthesis of a new series of para- and meta- substituted mono- and di- ferrocenyl phenols [2-ferrocenyl-1-(3- hydroxyphenyl)-1-phenyl-but-1-ene (6), 2-ferrocenyl-1-(3-hydroxyphenyl)-1-(4- hydroxyphenyl)-but-1-ene (7), 1,2-di-ferrocenyl-1-(4-hydroxyphenyl)-but-1-ene (8), and 1,2-di-ferrocenyl-1-(3-hydroxyphenyl)-but-1-ene (9)] and their electrochemical and biochemical properties, especially in comparison to the previously reported standard compounds [2-ferrocenyl-1-(4- hydroxyphenyl)-1-phenyl-but-1-ene (2) and (3)]. We also report the synthesis and characterization of the diphenyl analogue, 2-ferrocenyl-1,1-diphenyl-but-1-ene (5). This structure-activity relationship study was motivated by our hypothesis that the cytotoxicity of 3 is related to its ability to form a quinone methide structure after two in situ 1-electron oxidations, a process which requires the presence of at least one p-phenol. The mono-ferrocenyl compounds (including those previously reported) are reasonably well recognized by the oestrogen receptors ?? (RBAs = 0.9-9.6%) and β (RBAs = 0.28-16.3%), although the bulkier di-ferrocenyl compounds show very little affinity. In vitro, the cytotoxic effects of the phenolic complexes are related to the positioning of the hydroxyl group (para- superior to meta-), and to the number of ferrocenyl groups (one superior to two), with IC50 values against the MDA-MB-231 cell line ranging from 0.44-3.5 M. On the hormone-dependent breast cancer cell line MCF-7, the observed effect seems to be the result of two components, one cytotoxic (antiproliferative) and one estrogenic (proliferative). Electrochemical studies show that only the compounds with a p-phenol engage in proton-coupled intramolecular electron transfer. This journal is The Royal Society of Chemistry.