Methyl hypofluorite in the synthesis of 16-methoxyestradiol stereoisomers

Jonson, Stephanie D.; d’Avignon, D. André; Katzenellenbogen, John A.; Welch, Michael J.

doi:10.1016/s0039-128x(98)00051-8

Cited by 7 publications

(3 citation statements)

References 22 publications

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“…Previously, ER ligands have been labeled with fluorine-18 and other cyclotron-produced, short-lived radionuclides to develop in vivo imaging agents ( − ). For example, 16α-[ 18 F]fluoro-estradiol (FES) was used to image primary and metastatic breast tumors, and the FES images were shown to have value in predicting the clinical effectiveness of hormone therapy with tamoxifen, the most commonly used anti-estrogen drug ( , ).…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Functionalized Cyclopentadienyl Tricarbonylmetal Complexes for Technetium-94m PET Imaging of Estrogen Receptors

et al. 2005

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Cyclopentadienyl tricarbonylmetal (CpTM, M = Re, (94m)Tc) complexes, some based on a typical nonsteroidal estrogen, were prepared with the aim of developing technetium- and rhenium-labeled imaging agents for estrogen receptor (ER) positive breast tumors. CpT[(94m)Tc] compounds with simple cyclopentadienyl substituents were first synthesized using a modified double ligand transfer reaction. The in vivo biodistribution of one of these CpT[(94m)Tc] complexes was determined by tissue dissection and microPET imaging. Novel C-ring substituted analogues of cyclofenil, a nonsteroidal compound known to bind the ER, were also prepared, and their ER binding was measured. Because of their low ER affinity, however, labeling and imaging studies of these compounds were not pursued. It is notable that the highest ER binding analogue, a CpTRe cyclofenil derivative, could be synthesized from the corresponding ferrocenyl cyclofenil analogue by the double ligand transfer reaction. This further demonstrates the versatility of the double ligand transfer reaction and indicates that the synthesis of technetium and rhenium radiolabeled agents for breast tumor imaging and therapy is also likely to be successful.

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Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Functionalized Cyclopentadienyl Tricarbonylmetal Complexes for Technetium-94m PET Imaging of Estrogen Receptors

et al. 2005

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“…In the effort to develop a suitable PET imaging probe for the androgen receptor, three carbon-11 labeled hydroxyflutamide analogues (Fig. (9)) [85] were radiosynthesized via alkylation of the N-[ 11 C]alkylation of desmethyl amine with [ 11 C]methyl iodide in dimethylacetamide and then purified by reverse phase HPLC system. The total radiosynthesis took around 50 minutes with 10 -15% radiochemical yield (decay-corrected to EOB), > 99% radiochemical purity and 148 GBq/μmol specific activity (decay corrected to EOB).…”

Section: Androgen Receptor (Ar)mentioning

confidence: 99%

C-11 Radiochemistry in Cancer Imaging Applications

Mach

2010

CTMC

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Carbon-11 (C-11) radiotracers are widely used for the early diagnosis of cancer, monitoring therapeutic response to cancer treatment, and pharmacokinetic investigations of anticancer drugs. PET imaging permits non-invasive monitoring of metabolic processes and molecular targets, while carbon-11 radiotracers allow a "hot-for cold" substitution of biologically active molecules. Advances in organic synthetic chemistry and radiochemistry as well as improved automated techniques for radiosynthesis have encouraged investigators in developing carbon-11 tracers for use in oncology imaging studies. The short half-life of carbon-11 (20.38 minutes) creates special challenges for the synthesis of C-11 labeled tracers; these include the challenges of synthesizing C-11 target compounds with high radiochemical yield, high radiochemical purity and high specific activity in a short time and on a very small scale. The optimization of conditions for making a carbon-11 tracer include the late introduction of the C-11 isotope, the rapid formation and purification of the target compound, and the use of automated systems to afford a high yield of the target compound in a short time. In this review paper, we first briefly introduce some basic principles of PET imaging of cancer; we then discuss principles of carbon-11 radiochemistry, focus on specific advances in radiochemistry, and describe the synthesis of C-11 radiopharmaceuticals developed for cancer imaging. The carbon-11 radiochemistry approaches described include the N,O, and S-alkylations of [(11)C]methyl iodide/[(11)C]methyl triflate and analogues of [(11)C]methyl iodide and their applications for making carbon-11 tracers; we then address recent advances in exploring a transmetallic complex mediated [(11)C]carbonyl reaction for oncologic targets.

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“…The reaction of methyl hypofluorite with the 17-trimethylsilylenol ether of 3-benzyloxyestrone has afforded 86 routes for the introduction of a 16α-and 16β-methoxy group which were examined for their estrogen receptor binding affinity. The 17αand 17β-aminoestra-1,3,5(10)-trien-3-ols have been prepared.…”

Section: Estranesmentioning

confidence: 99%

Steroids: reactions and partial synthesis (1998)

Hanson¹

2000

Nat. Prod. Rep.

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Methyl hypofluorite in the synthesis of 16-methoxyestradiol stereoisomers

Cited by 7 publications

References 22 publications

Design and Synthesis of Functionalized Cyclopentadienyl Tricarbonylmetal Complexes for Technetium-94m PET Imaging of Estrogen Receptors

Design and Synthesis of Functionalized Cyclopentadienyl Tricarbonylmetal Complexes for Technetium-94m PET Imaging of Estrogen Receptors

C-11 Radiochemistry in Cancer Imaging Applications

Steroids: reactions and partial synthesis (1998)

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