14303-48-1Relevant articles and documents
Synthesis and evaluation of fluoroethyl cyclofenil analogs: Models for potential estrogen receptor imaging agent
Zhu, Hua,Yang, Zhi,Lin, Jian-Guo,Luo, Shi-Neng,Shen, Yu-Mei
scheme or table, p. 46 - 52 (2012/07/28)
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.
Design, synthesis, and evaluation of cyclofenil derivatives for potential SPECT imaging agents
Zhu, Hua,Huang, Liliang,Zhang, Yuanqing,Xu, Xiaoping,Sun, Yanhong,Shen, Yu-Mei
experimental part, p. 591 - 599 (2011/10/18)
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.
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
Seo, Jai Woong,Comninos, John S.,Chi, Dae Yoon,Kim, Dong Wook,Carlson, Kathryn E.,Katzenellenbogen, John A.
, p. 2496 - 2511 (2007/10/03)
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.
