5-bromo-3-oxindolenine | 1610056-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-bromo-3-oxindolenine
• CAS: 1610056-03-5
• 化学式: C₈H₄BrNO
• 分子量: 210.03
• InChiKey: OQWZFMUXWBUGNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.43
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-bromo-3-oxindolenine 在 sodium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  [EN] MICROMOLECULAR PCSK9 PROTEIN DEGRADATION AGENT, PREPARATION METHOD THEREFOR, AND USE THEREOF
  [FR] AGENT DE DÉGRADATION DE PROTÉINE PCSK9 MICROMOLÉCULAIRE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION
  [ZH] 一种PCSK9小分子蛋白降解剂及其制备方法和应用

  摘要：

  本发明提供一种PCSK9小分子蛋白降解剂及其制备方法，所述PCSK9小分子抑制剂为如下式化学结构通式(I)的四氢异喹啉类化合物或其药学上可接受的盐或溶剂化物：这类化合物具有降解PCSK9或降解LC3的作用，可用于制备预防或治疗与抑制PCSK9或LC3活性相关的疾病的药物。

  公开号：

  WO2023165373A1
• 作为产物：
  描述：

  5-溴吲哚 在 ferric WT dehaloperoxidase hemoglobin B 、 双氧水 作用下， 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 0.08h， 以47%的产率得到5-bromo-3-oxindolenine
  参考文献：
  名称：

  Peroxygenase and Oxidase Activities of Dehaloperoxidase-Hemoglobin from Amphitrite ornata

  摘要：

  The marine globin dehaloperoxidase-hemoglobin (DHP) from Amphitrite ornata was found to catalyze the H2O2-dependent oxidation of monohaloindoles, a previously unknown class of substrate for DHP. Using 5-Br-indole as a representative substrate, the major monooxygenated products were found to be 5-Br-2-oxindole and 5-Br-3-oxindolenine. Isotope labeling studies confirmed that the oxygen atom incorporated was derived exclusively from H2O2, indicative of a previously unreported peroxygenase activity for DHP. Peroxygenase activity could be initiated from either the ferric or oxyferrous states with equivalent substrate conversion and product distribution. It was found that 5-Br-3-oxindole, a precursor of the product 5-Br-3-oxindolenine, readily reduced the ferric enzyme to the oxyferrous state, demonstrating an unusual product-driven reduction of the enzyme. As such, DHP returns to the globin-active oxyferrous form after peroxygenase activity ceases. Reactivity with 5-Br-3-oxindole in the absence of H2O2 also yielded 5,5'-Br-2-indigo above the expected reaction stoichiometry under aerobic conditions, and O-2-concentration studies demonstrated dioxygen consumption. Nonenzymatic and anaerobic controls both confirmed the requirements for DHP and molecular oxygen in the catalytic generation of 5,5'-Br-2-indigo, and together suggest a newly identified oxidase activity for DHP.

  DOI：

  10.1021/ja500293c

文献信息

• Peroxygenase and Oxidase Activities of Dehaloperoxidase-Hemoglobin from <i>Amphitrite ornata</i>
  作者：David A. Barrios、Jennifer D’Antonio、Nikolette L. McCombs、Jing Zhao、Stefan Franzen、Andreas C. Schmidt、Leslie A. Sombers、Reza A. Ghiladi

  DOI：10.1021/ja500293c

  日期：2014.6.4

  The marine globin dehaloperoxidase-hemoglobin (DHP) from Amphitrite ornata was found to catalyze the H2O2-dependent oxidation of monohaloindoles, a previously unknown class of substrate for DHP. Using 5-Br-indole as a representative substrate, the major monooxygenated products were found to be 5-Br-2-oxindole and 5-Br-3-oxindolenine. Isotope labeling studies confirmed that the oxygen atom incorporated was derived exclusively from H2O2, indicative of a previously unreported peroxygenase activity for DHP. Peroxygenase activity could be initiated from either the ferric or oxyferrous states with equivalent substrate conversion and product distribution. It was found that 5-Br-3-oxindole, a precursor of the product 5-Br-3-oxindolenine, readily reduced the ferric enzyme to the oxyferrous state, demonstrating an unusual product-driven reduction of the enzyme. As such, DHP returns to the globin-active oxyferrous form after peroxygenase activity ceases. Reactivity with 5-Br-3-oxindole in the absence of H2O2 also yielded 5,5'-Br-2-indigo above the expected reaction stoichiometry under aerobic conditions, and O-2-concentration studies demonstrated dioxygen consumption. Nonenzymatic and anaerobic controls both confirmed the requirements for DHP and molecular oxygen in the catalytic generation of 5,5'-Br-2-indigo, and together suggest a newly identified oxidase activity for DHP.
• [EN] MICROMOLECULAR PCSK9 PROTEIN DEGRADATION AGENT, PREPARATION METHOD THEREFOR, AND USE THEREOF<br/>[FR] AGENT DE DÉGRADATION DE PROTÉINE PCSK9 MICROMOLÉCULAIRE, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION<br/>[ZH] 一种PCSK9小分子蛋白降解剂及其制备方法和应用
  申请人：UNIV FUDAN

  公开号：WO2023165373A1

  公开（公告）日：2023-09-07

  本发明提供一种PCSK9小分子蛋白降解剂及其制备方法，所述PCSK9小分子抑制剂为如下式化学结构通式(I)的四氢异喹啉类化合物或其药学上可接受的盐或溶剂化物：这类化合物具有降解PCSK9或降解LC3的作用，可用于制备预防或治疗与抑制PCSK9或LC3活性相关的疾病的药物。