Hydroboration of vinylsilanes providing diversity-oriented hydrophobic building blocks for biofunctional molecules.
Org Biomol Chem
; 22(30): 6115-6121, 2024 Jul 31.
Article
em En
| MEDLINE
| ID: mdl-38826124
ABSTRACT
Hydroboration of vinylsilanes with BH3 affords two silylethanol regioisomers. Herein, we investigated the regioisomeric ratio of hydroboration products from various vinylsilanes, focusing on the characteristic reaction profile. All investigated vinylsilanes afforded both regioisomers, and greater bulkiness increased the proportion of the Markovnikov products. The obtained silylethanols were used as hydrophobic building blocks for constructing nuclear progesterone receptor (PR) modulators. Notably, structural conversions from an α-isomer (silylethan-1-oxy derivative) to a ß-isomer (2-silylethoxy derivative) caused complete activity-switching from a PR agonist to an antagonist. Our results indicate that silylethanols are useful for structural development, and vinylsilanes are a versatile source of hydrophobic building blocks for obtaining biofunctional molecules.
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MEDLINE
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En
Ano de publicação:
2024
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Article