An Efficient Regioselective Preparation of Fulvestrant

Mohanraj, Senthil Kumar Pichandi; Tulasi, Ramachar; Subramanian, V.

doi:10.1080/00304948.2021.1908046

Cited by 3 publications

(3 citation statements)

References 12 publications

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“…The −S-(CH 2 ) 3 -CF 2 -CF 3 group found in DD-1–DD-6 maintains the CF 2 group adjacent to CH 2 , which was the second most responsive fluorine group in 1 and 2 . Such a tail has been produced on large scale providing a readily available functional group as it is a key building block for the synthesis of the FDA-approved drug, fulvestrant . Finally, sulfide oxidation states were modified in DD-2 , DD-4 , and DD-6 to evaluate the heteroatom effects on thermal responsiveness.…”

Section: Resultsmentioning

confidence: 99%

“…Such a tail has been produced on large scale providing a readily available functional group as it is a key building block for the synthesis of the FDA-approved drug, fulvestrant. 31 Finally, sulfide oxidation states were modified in DD-2, DD-4, and DD-6 to evaluate the heteroatom effects on thermal responsiveness.…”

Section: F Nmr Aqueous Solubility Limit Measurementsmentioning

confidence: 99%

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Fluorous Liquids for Magnetic Resonance-Based Thermometry with Enhanced Responsiveness and Environmental Degradation

Mundhenke

Smith

et al. 2023

Anal. Chem.

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Accurate temperature measurement via magnetic resonance is valuable for both in vitro and in vivo analysis of local tissue for evaluating disease pathology and medical interventions. 1 H MRI-based thermometry is used clinically but is susceptible to error from magnetic field drift and low sensitivity in fatty tissue and requires a reference for absolute temperature determination. As an alternative, perfluorotributylamine (PFTBA), a perfluorocarbon liquid for 19 F MRI thermometry, is based on chemical shift responsiveness and approaches the sensitivity of 1 H MRI thermometry agents; however, environmental persistence, greenhouse gas concerns, and multiple resonances which can lead to MRI artifacts indicate a need for alternative sensors. Using a 19 F NMR-based structure−property study of synthetic organofluorine molecules, this research develops new organofluorine liquids with improved temperature responsiveness, high signal, and reduced nonmagnetically equivalent fluorine resonances. Environmental degradation analysis using reverse-phase HPLC and quantitative 19 F NMR demonstrates a rapid degradation profile mediated via the aryl fluorine core of temperature sensors. Our findings show that our lead liquid temperature sensor, DD-1, can be made in high yield in a single step and possesses an improved responsiveness over our prior work and an 83% increase in aqueous thermal responsiveness over PFTBA. Degradation studies indicate robust degradation with half-lives of less than two hours under photolysis conditions for the parent compound and formation of other fluorinated products. The improved performance of DD-1 and its susceptibility to environmental degradation highlight a new lead fluorous liquid for thermometry applications.

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Section: Resultsmentioning

confidence: 99%

Section: F Nmr Aqueous Solubility Limit Measurementsmentioning

confidence: 99%

Fluorous Liquids for Magnetic Resonance-Based Thermometry with Enhanced Responsiveness and Environmental Degradation

Mundhenke

Smith

et al. 2023

Anal. Chem.

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“…Dehydronandrolone acetate ( 3 ) is a key precursor in the synthesis of C7-functionalized steroidal drugs such as the new antibreast cancer drug Fulvestrant, the treatment of menopause and postmenopausal syndrome drug Tibolone, as well as the highly effective protein anabolic hormone Mibolone . It is known that the market for C7-functionalized steroidal drugs is huge.…”

mentioning

confidence: 99%

A Designed Chemoenzymatic Route for Efficient Synthesis of 6-Dehydronandrolone Acetate: A Key Precursor in the Synthesis of C7-Functionalized Steroidal Drugs

Zhang,

Gao,

Zhao

et al. 2023

ACS Catal.

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Dehydronandrolone acetate (3) is a crucial precursor for the synthesis of C7-functionalized steroidal drugs. However, the current production method involves a laborious and environmentally unfriendly five-step chemical process, resulting in a low efficiency. To overcome this, we report a chemoenzymatic strategy, involving a one-pot biocatalytic C7β-hydroxylation/C17β-ketoreduction of 19-norandrostenedione (1) by combination of P450 monooxygenase and 17-ketosteroid reductase to generate C7β-hydroxynandrolone (2) as an intermediate, followed by a one-pot chemical dehydration and esterification to form 3. Impressively, the gram-scale synthesis of 3 was achieved with 93% isolated yield, which outperforms the traditional chemical approach (68% yield), thereby signaling great potential for industrial applications.

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Lapatinib- and fulvestrant-PAMAM dendrimer conjugates promote apoptosis in chemotherapy-induced senescent breast cancer cells with different receptor status

Lewińska

Wróbel²,

Błoniarz³

et al. 2022

Biomaterials Advances

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An Efficient Regioselective Preparation of Fulvestrant

Cited by 3 publications

References 12 publications

Fluorous Liquids for Magnetic Resonance-Based Thermometry with Enhanced Responsiveness and Environmental Degradation

Fluorous Liquids for Magnetic Resonance-Based Thermometry with Enhanced Responsiveness and Environmental Degradation

A Designed Chemoenzymatic Route for Efficient Synthesis of 6-Dehydronandrolone Acetate: A Key Precursor in the Synthesis of C7-Functionalized Steroidal Drugs

Lapatinib- and fulvestrant-PAMAM dendrimer conjugates promote apoptosis in chemotherapy-induced senescent breast cancer cells with different receptor status

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