(3,5-二溴-4-羟基苯基)-[2-(1-羟基乙基)-1-苯并呋喃-3-基]甲酮 | 125729-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3,5-二溴-4-羟基苯基)-[2-(1-羟基乙基)-1-苯并呋喃-3-基]甲酮
• 英文名称: (3,5-dibromo-4-hydroxyphenyl)-[2-(1-hydroxyethyl)benzofuran-3-yl]methanone
• 英文别名: 1'-hydroxybenzbromarone；1'-hydroxy-BBR；(3,5-dibromo-4-hydroxyphenyl)-[2-(1-hydroxyethyl)-1-benzofuran-3-yl]methanone
• CAS: 125729-46-6
• 化学式: C₁₇H₁₂Br₂O₄
• 分子量: 440.088
• InChiKey: ZYHWDBVIUWBPCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3,5-二溴-4-羟基苯基)-[2-(1-羟基乙基)-1-苯并呋喃-3-基]甲酮 生成 1-[3-(3,5-Dibromo-4-hydroxybenzoyl)-1-benzofuran-2-yl]ethanone
  参考文献：
  名称：

  MAURER, H.;WOLLENBERG, P., ARZNEIM.-FORSCH., 40,(1990) N, C. 460-462

  摘要：

  DOI：
• 作为产物：
  描述：

  苯溴马隆 生成 (3,5-二溴-4-羟基苯基)-[2-(1-羟基乙基)-1-苯并呋喃-3-基]甲酮
  参考文献：
  名称：

  MAURER, H.;WOLLENBERG, P., ARZNEIM.-FORSCH., 40,(1990) N, C. 460-462

  摘要：

  DOI：

文献信息

• Use of small molecule inhibitors targeting EYA tyrosine phosphatase
  申请人：Children's Hospital Medical Center

  公开号：US10221151B2

  公开（公告）日：2019-03-05

  Inhibitors of EYA tyrosine phosphatase are provided herein, as well as pharmaceutical compositions and methods relating thereto.

  本文提供了 EYA 酪氨酸磷酸酶的抑制剂以及与之相关的药物组合物和方法。
• Charge and Substituent Effects on Affinity and Metabolism of Benzbromarone-Based CYP2C19 Inhibitors
  作者：Charles W. Locuson、Hisashi Suzuki、Allan E. Rettie、Jeffrey P. Jones

  DOI：10.1021/jm049605m

  日期：2004.12.1

  Human cytochrome P450 (CYP) 2C19 is one of the most important CYP2C family members responsible for metabolizing commonly prescribed drugs. This research describes synthetic modifications to benzbromarone (Bzbr) to create the most potent CYP2C19 inhibitor ever reported. The most important features enabling analogues of Bzbr to bind to CYP2C19 with high affinity are low acidity (high pK(a) or nonionizability) and hydrophobic substituents adjacent to the phenol moiety. Though CYP2C19 was known to prefer neutral substrates, the extent was perhaps not realized until the anionic, parent compound Bzbr (K-i = 3.7 muM) was compared to a less acidic dimethyl analogue (K-i = 0.033 muM). However, differences in affinity for anionic and neutral Bzbr analogues did not appear to affect the regiospecificity of their metabolism by CYP's 2C19 and 2C9. In addition, some Bzbr analogues were metabolized both on the phenol and benzofuran rings. By using a substrate with a methyl ether in place of the Bzbr phenol, it was shown that some Bzbr analogues must be able to freely reposition after binding and oxidize the more energetically favorable position. Normally, O-demethylation of this methyl ether is favored over benzofuran hydroxylation based on ion current from LC/MS. Deuterium substitution of the methyl ether results in an inverse isotope effect on benzofuran hydroxylation (i.e. increased oxidation of this less favorable site). Likewise, Bzbr-based CoMFA models of CYP2C19 demonstrated no clear preference for any one ligand alignment. This suggests results from this modeling method must be interpreted carefully for each CYP isoform. In summary, Bzbr analogues have demonstrated they can be adapted to other CYP2C enzymes in order to probe isoform-specific properties.
• MAURER, H.;WOLLENBERG, P., ARZNEIM.-FORSCH., 40,(1990) N, C. 460-462
  作者：MAURER, H.、WOLLENBERG, P.

  DOI：——

  日期：——
• USE OF SMALL MOLECULE INHIBITORS TARGETING EYA TYROSINE PHOSPHATASE
  申请人：Children's Hospital Medical Center

  公开号：US20140128460A1

  公开（公告）日：2014-05-08

  Inhibitors of EYA tyrosine phosphatase are provided herein, as well as pharmaceutical compositions and methods relating thereto.
• INHIBITORS OF EYA3-PROTEIN TYROSINE PHOSPHATASE IN DNA DAMAGE REPAIR SIGNALING OF PULMONARY ARTERIAL HYPERTENSION
  申请人：CHILDREN'S HOSPITAL MEDICAL CENTER

  公开号：US20210130312A1

  公开（公告）日：2021-05-06

  Inhibitors of EYA3-protein tyrosine phosphatase are provided herein, as well as pharmaceutical compositions and methods relating thereto.