関連する実験動画

Updated: Sep 9, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

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17α-ピコリルおよび17(E) -ピコリニリデンアンドロスタンの誘導体によるアルドケト還元酵素1C3抑制の構造的基礎

Jovana J Plavša-Puž1, Jiří Brynda2, Jovana J Ajduković3

  • 1Department of Biology and Ecology, University of Novi Sad, Novi Sad, Serbia.

Journal of enzyme inhibition and medicinal chemistry
|September 4, 2025
PubMed
まとめ

アンドロスタンの新しい派生物は,ステロイド変異酵素アルドケト還元酵素1C3 (AKR1C3) を効果的に抑制し,がんの進行に不可欠です. これらの化合物はアンドロゲン受容体への親和性を示せず,標的がん治療の有望な道を示しています.

キーワード:
AKR1C3CYP17分子ドッキング前立腺がんタンパク質のX線結晶学

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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Phase I biotransformation reactions are integral to drug metabolism, predominantly involving oxidative, reductive, and hydrolytic transformations. Chief among these are oxidative reactions, which enhance the hydrophilicity of xenobiotics and introduce polar functional groups to facilitate their elimination from the body.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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