177840-82-3

Upstream product

• 177840-81-2 2-ferrocenyl-1,1'-bis(4-methoxyphenyl)-but-1-ene 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 1271-55-2 acetylferrocene 

Downstream Products

• 1030632-83-7 2-ferrocenyl-1,1'-bis(4-acetoxyphenyl)-but-1-ene 
• 1291080-38-0 1-(4-hydroxyphenyl)-1-(4-pivaloyloxyphenyl)-2-ferrocenyl-but-1-ene 
• 1291080-35-7 1,1-bis[4-(3-dimethylaminopropoxy)phenyl]-2-ferrocenyl-but-1-ene 
• 177840-83-4 [Fe(C₅H₅)(C₅H₄C(C₂H₅)C(C₆H₄OCH₂CH₂N(CH₃)2)2)] 

Relevant academic research and scientific papers

Efficient synthesis of ferrocifens and other ferrocenyl-substituted ethylenes: Via a 'sulfur approach'

Stable and non-odorous alkyl ferrocenyl thioketones react with bis(4-methoxyphenyl)diazomethane according to the 'two-fold extrusion' reaction principles, and tetrasubstituted ethylenes obtained thereby can be demethylated to give (Fc,2OH)-ferrocifens in good yields. The method offers an alternative approach to this class of medically relevant compounds. A similar protocol with alkyl ferrocenyl thioketones and selected diaryldiazomethanes leads to ferrocenyl-substituted ethylenes including dibenzofulvenes. These products are of potential interest for electrochemical and photophysical studies.

Organometallic SERMs (selective estrogen receptor modulators): Cobaltifens, the (cyclobutadiene)cobalt analogues of hydroxytamoxifen

The McMurry coupling of (tetraphenylcyclobutadiene)cobalt(cyclopentadienyl) ketones, (C4Ph4)Co[C5H4C({double bond, long}O)R], where R = Me, 3a, or Et, 3b, with a range of substituted benzophenones furnished a se

Ferrocenyl compounds possessing protected phenol and thiophenol groups: Synthesis, X-ray structure, and in vitro biological effects against breast cancer

We have previously shown that conjugated ferrocenyl p-phenols show strong cytotoxic effects against both the hormone-dependent MCF-7 and hormone-independent MDA-MB-231 breast cancer cell lines, possibly via metabolic quinone methide (QM) formation. To fur

Organometallic diphenols: The importance of the organometallic moiety on the expression of a cytotoxic effect on breast cancer cells

We have recently reported that the ferrocenyl diphenol compound 1,1-di(4-hydroxyphenyl)-2-ferrocenyl-but-1-ene 1 exhibited strong in vitro anti-proliferative effects on both hormone dependent (MCF7, IC50 = 0.7 μM) and hormone independent (MDA-MB231, IC50 = 0.6 μM) breast cancer cells. In order to assess the importance of the ferrocenyl motif, we have prepared a series of analogs using the organometallic fragments (η5-C5H4)Cp*Fe (7), ((η5-C5H4)(CH3)2phospholyl)Fe (9), (η5-C5H4)CpRu (10), (η5-C5H4)Re(CO)3 (11), and (η5-C5H4)Mn(CO)3 (12), and the chlorinated ferrocenyl derivative 1,1-di(4-hydroxyphenyl)-2-ferrocenyl-4-chloro-but-1-ene (4). The nature of the organometallic moiety had a strong influence on estrogen receptor alpha (ERα) recognition, with relative binding affinity (RBA) values ranging from 0.55% to 10.8%. The second isoform of the estrogen receptor, ERβ, was better able to accommodate these compounds, with RBA values ranging from 8.9% to 17.1%. Molecular modeling studies suggest that the orientation of the compounds and their interactions with the residues of ERα and ERβ binding sites are very similar. A study on the MCF7 hormone dependent breast cancer cell line revealed an anti-proliferative effect for the ferrocenyl phenols 1 and 4, while the other compounds displayed either a proliferative effect (9-12), or no effect (7). The anti-proliferative effect of 1 and 4 is also evident in the MDA-MB231 hormone independent breast cancer cell line (IC50(4) = 1 μM), and can be attributed to the cytotoxicity of these compounds, while the other compounds showed no effect on this cell line. The cytotoxicity of 1 and 4 may arise from electron delocalization in the radical cation in alkaline conditions, possibly resulting in a cytotoxic quinone methide formation, while the other complexes do not undergo the formation of this entity, as evidenced by the electrochemical results.

Ferrocenyl hydroxytamoxifen: A prototype for a new range of oestradiol receptor site-directed cytotoxics

The synthesis of ferrocenyl hydroxytamoxifen 1, a prototype for a new range of oestradiol receptor site-directed cytotoxic compounds, and some preliminary biochemical tests are reported.