5189-40-2

Usage

Uses

Used in Electronic Components Industry:
4,4'-Cyclohexylidenemethylenediphenol is used as a heat-resistant and transparent material for manufacturing electronic components. Its high thermal stability and resistance to chemicals make it suitable for creating durable and long-lasting components that can withstand the demands of electronic devices.
Used in Optical Lenses Industry:
In the optical lenses industry, 4,4'-Cyclohexylidenemethylenediphenol is utilized as a material for producing lenses with high transparency and heat resistance. Its properties ensure that the lenses maintain their clarity and functionality even under high-temperature conditions.
Used in Protective Coatings Industry:
4,4'-Cyclohexylidenemethylenediphenol is employed as a key ingredient in the formulation of protective coatings. Its ability to withstand high temperatures and resist chemical degradation makes it an ideal choice for coatings that provide long-lasting protection to various surfaces.

InChI:InChI=1/C19H20O2/c20-17-10-6-15(7-11-17)19(14-4-2-1-3-5-14)16-8-12-18(21)13-9-16/h6-13,20-21H,1-5H2

Upstream product

• 4630-82-4 methyl cyclohexylcarboxylate 
• 17878-44-3 (4-bromophenoxy)trimethylsilane 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 108-94-1 cyclohexanone 
• 2624-43-3 cyclofenil 
• 10218-57-2 1,1'-(cyclohexylidenemethylene)bis(4-methoxy)benzene 
• 3289-28-9 ethyl cyclohexanecarboxylate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Downstream Products

• 2624-43-3 cyclofenil 
• 918803-14-2 4-((4-(2-aminoethoxy)phenyl)(cyclohexylidene)methyl)phenol 
• 1220520-47-7 ethyl 6-[4-[cyclohexylidene(4-hydroxyphenyl)methyl]phenoxy]hexanoate 
• 1220520-44-4 (4-(tert-butyldimethylsilyloxy)phenyl)(4-hydroxyphenyl)methylenecyclohexane 
• 1242078-07-4 (4-(2-fluoroethoxy)phenyl)-(4-hydroxyphenyl)methylenecyclohexane 
• 1246852-94-7 2-(4-((4-(4,5-dimethoxy-2-nitrobenzyloxy)phenyl)(cyclohexylidene)methyl)phenoxy)-N,N-dimethylethanamine 
• 1246852-95-8 4-((4-((4-(2-(dimethylamino)ethoxy)phenyl)(cyclohexylidene)methyl)phenoxy)methyl)-6-bromo-7-hydroxycoumarin 
• 110024-82-3 4-((4-(2-(dimethylamino)ethoxy)phenyl)(cyclohexylidene)methyl)-phenol 
• 1224593-67-2 C₃₅H₃₉N₃O₂ 
• 1224593-62-7 C₂₃H₂₇BrO₂ 

Relevant academic research and scientific papers

Optical control of protein activity and gene expression by photoactivation of caged cyclofen

The use of light to control the expression of genes and the activity of proteins is a rapidly expanding field. While many of these approaches use a fusion between a light activatable protein and the protein of interest to control the activity of the latter, it is also possible to control the activity of a protein by uncaging a specific ligand. In that context, controlling the activation of a protein fused to the modified estrogen receptor (ERT) by uncaging its ligand cyclofen-OH has emerged as a generic and versatile method to control the activation of proteins quantitatively, quickly and locally in a live organism. Here, we present the experimental details behind this approach.

SYNTHESIS OF PHOTOACTIVABLE CAGED CYCLOFEN-OH AND DERIVATIVES THEREOF

The present invention relates to a new process of manufacturing of caged cyclofen-OH and derivatives thereof, of formula (I) or salts thereof, wherein n, R1, R1 ', R2, and R3 are as defined in the claims.

Synthesis and evaluation of fluoroethyl cyclofenil analogs: Models for potential estrogen receptor imaging agent

Cyclofenil analogs (2a-2f) and their fluorine-containing derivatives (3a-3f) were synthesized and evaluated as candidate ligands for positron emission tomography (PET) imaging of estrogen receptors. Most of them show relatively high binding affinities comparable with estradiol (E2). (4-Fluoroethoxyphenyl)-(4-hydroxyphenyl) methylenecyclopentane (3a) showed both the highest binding affinity for ERs (88.6 for ERβ, 13.8 for ERα) and highest β/α ratio (β/α for 6.4-fold). The radioactive compound [18F]3a was prepared via displacement of the corresponding mesylate precursor 4 with [18F]fluoride (18F: β+; 96.7%, T1/2 = 109.8 min). The biodistribution studies in immature female SD rats demonstrated that the uptake in the uterus and ovaries were 1.358 ± 0.089% ID/g, 1.439 ± 0.214% ID/g, respectively, both of the ratios of uterus/blood and ovaries/blood was less than 2:1. Micro-PET imaging of immature female SD rats has also been reported.

Photocontrol of protein activity in cultured cells and zebrafish with one- and two-photon illumination

We have implemented a noninvasive optical method for the fast control of protein activity in a live zebrafish embryo. It relies on releasing a protein fused to a modified estrogen receptor ligand binding domain from its complex with cytoplasmic chaperones, upon the local photoactivation of a nonendogenous caged inducer. Molecular dynamics simulations were used to design cyclofen-OH, a photochemically stable inducer of the receptor specific for 4-hydroxy-tamoxifen (ERT2). Cyclofen-OH was easily synthesized in two steps with good yields. At submicromolar concentrations, it activates proteins fused to the ERT2 receptor. This was shown in cultured cells and in zebrafish embryos through emission properties and subcellular localization of properly engineered fluorescent proteins. Cyclofen-OH was successfully caged with various photolabile protecting groups. One particular caged compound was efficient in photoinducing the nuclear translocation of fluorescent proteins either globally (with 365 nm UV illumination) or locally (with a focused UV laser or with two-photon illumination at 750 nm). The present method for photocontrol of protein activity could be used more generally to investigate important physiological processes (e.g., in embryogenesis, organ regeneration and carcinogenesis) with high spatiotemporal resolution.

Practical synthesis of FEt-penta-cyclofenil and its derivatives for potential PET imaging

Generally, FEt-penta-cyclofenil and its derivatives have greater relative binding affinity to estradiol receptors than estradiol. (4-Fluoroethoxyphenyl)- (4'-hydroxyphenyl) methylenecyclopentane and its derivatives were synthesized for potential radioactive image agents, and their structures were characterized by ultraviolet, infrared, 1H NMR, 19F NMR, and high-resolution mass spectrometry. Copyright

Characterization of the pharmacophore properties of novel selective estrogen receptor downregulators (SERDs)

Selective estrogen receptor (ER) down-regulators (SERDs) reduce ERα protein levels as well as block ER activity and therefore are promising therapeutic agents for the treatment of hormone refractory breast cancer. Starting with the triarylethylene acrylic acid SERD 4, we have investigated how alterations in both the ligand core structure and the appended acrylic acid substituent affect SERD activity. The new ligands were based on high affinity, symmetrical cyclofenil or bicyclo[3.3.1]nonane core systems, and in these, the position of the carboxyl group was extended from the ligand core, either retaining the vinylic linkage of the substituent or replacing it with an ether linkage. Although most structural variants showed binding affinities for ERα and ERβ higher than that of 4, only the compounds preserving the acrylic acid side chain retained SERD activity, although they could possess varying core structures. Hence, the acrylic acid moiety of the ligand is crucial for SERD-like blockade of ER activities.

Design, synthesis, and evaluation of cyclofenil derivatives for potential SPECT imaging agents

To develop technetium- and rhenium-labeled nonsteroidal estrogen imaging agents for estrogen receptor (ER) positive breast tumors, two groups of rhenium and technetium cyclofenil derivatives were synthesized and characterized. The binding affinities of the rhenium complexes for ERs were determined. The tricarbonyl rhenium complex showed the highest binding affinity for ERs (81.2 for ERβ, 16.5 for ERα). Tricarbonyl technetium cyclofenil complexes were obtained in high radiochemical purity and radiochemical yields. The results of studies of their octanol/water partition and in vitro stability are presented. These results demonstrate that these radiolabeled cyclofenil derivatives may be considered as potential breast cancer imaging agents. SBIC 2010.

Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone

(Chemical Equation Presented) 2,2-Bis-(4-hydroxyphenyl)-cyclopentanone (3a) was unexpectedly obtained in 76% yield from a reductive coupling reaction of 4,4′-dihydroxybenzophenone (1a) and cyclobutanone with TiCl4 and Zn. Further optimization showed that catechol as an external ligand and a hydroxy group on benzophenone facilitated the generation of a quinonemethide (intermediate II) that is involved in the pinacol-type rearrangement of intermediate I to give the rearranged product.

Fluorine-substituted cyclofenil derivatives as estrogen receptor ligands: Synthesis and structure-affinity relationship study of potential positron emission tomography agents for imaging estrogen receptors in breast cancer

In a search for estrogen receptor (ER) ligands to be radiolabeled with fluorine-18 for imaging of ER-positive breast tumors with positron emission tomography (PET), we investigated cyclofenil analogues substituted at the C3 or C4 position of the cyclohexyl group. McMurry coupling of 4,4′- dihydroxybenzophenone with various ketones produced key cyclofenil intermediates, from which C3 and C4 substituents containing alkyl and various oxygen or fluorine-substituted alkyl groups were elaborated. Binding assays to both ERα and ERβ revealed that the C3 site is more tolerant of steric bulk and polar groups than the C4 site, consistent with a computational model of the ERα ligand binding pocket. Fluorine substitution is tolerated very well at some sites, giving some compounds having affinities comparable to or higher than that of estradiol. These fluoro and fluoroalkyl cyclofenils merit further consideration as fluorine-18 labeled ER ligands for PET imaging of ERs in breast tumors.

Cytotoxicity and antiestrogenicity of a novel series of basic diphenylethylenes

On the premise that it is necessary to develop antiestrogens with a higher cytotoxic component in order to reduce the risks of the development of heterogeneous malignant cell populations in breast cancer, we studied a novel series of basic diphenylethylenes, for the most part devoid of estrogenic activity, with low antiestrogenicity but much enhanced cytotoxicity compared to the reference drug tamoxifen. The main structural features associated with cytotoxicity were E isomery, substituents of five to eight carbons on the ethylene bond, and dibasicity.