Site-Selective Synthesis of 3,17-Diaryl-1,3,5,16-estratetraenes

Jopp, Stefan; Ehlers, Peter; Frank, Éva; Mernyák, Erzsébet; Schneider, Gyula; Wölfling, János; Villinger, Alexander; Langer, Peter

doi:10.1055/s-0037-1611720

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Cited by 4 publications

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Nucleophilic Aromatic Substitution

Crampton¹

2023

Organic Reaction Mechanisms Series

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Nucleophilic Aromatic Substitution

Crampton¹

2023

Organic Reaction Mechanisms Series

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Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Ziems,

Komabayashi,

Lehmann

et al. 2024

Eur J Org Chem

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The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl‐protected glucosyl imidazolium iodides as NHC‐precursors and 15 complexes have been synthesized. The structure‐activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki‐Miyaura between bromobenzene and 4‐tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.

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Pd-catalyzed Suzuki–Miyaura couplings and evaluation of 13α-estrone derivatives as potential anticancer agents

et al. 2020

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13α-Estrones are of great value owing to their potent multiple bioactivity, including anticancer activity. 3-OH or 3-OBn derivatives of 2-or 4-[(subst.) phenyl]-13α-estrone as potential antiproliferative agents have been synthesized via facile, microwave-induced, Pd-catalyzed Suzuki-Miyaura coupling. 2-or 4-Halogenated 13α-estrone derivatives have been reacted with (4-subst.)phenylboronic acids using Pd(PPh3)4 as catalyst. The nature of para substituents at the introduced phenyl group did not influence the outcome of couplings. Certain newly synthesized compounds displayed substantial antiproliferative action against human adherent cancer cell lines of gynecological origin. Important structure-activity relationships were revealed, which might be helpful in the design of potent and selective anticancer derivatives based on the hormonally inactive 13α-estrane core.

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Site-Selective Synthesis of 3,17-Diaryl-1,3,5,16-estratetraenes

Cited by 4 publications

References 5 publications

Nucleophilic Aromatic Substitution

Nucleophilic Aromatic Substitution

Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Pd-catalyzed Suzuki–Miyaura couplings and evaluation of 13α-estrone derivatives as potential anticancer agents

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Site-Selective Synthesis of 3,17-Diaryl-1,3,5,16-estratetraenes

Cited by 4 publications

References 5 publications

Nucleophilic Aromatic Substitution

Nucleophilic Aromatic Substitution

Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

Pd-catalyzed Suzuki–Miyaura couplings and evaluation of 13α-estrone derivatives as potential anticancer agents

Contact Info

Product

Resources

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Structure‐Activity Relationships of Glucose‐based Pd^II‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction