5,7-dichloro-3-phenylbenzofuran | 54923-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5,7-dichloro-3-phenylbenzofuran
• 英文别名: 3-Phenyl-5,7-dichloro-benzofuran；5,7-dichloro-3-phenyl-1-benzofuran
• CAS: 54923-52-3
• 化学式: C₁₄H₈Cl₂O
• 分子量: 263.123
• InChiKey: YFAJGIXSSVOJTA-UHFFFAOYSA-N

物化性质

• 沸点：
  387.8±42.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(2,4-二氯苯氧基)-1-苯基乙酮 以70%的产率得到
  参考文献：
  名称：

  ROCHE, M.;CERUTTI, E., ANN. SCI. UNIV. BESANCON. CHEM., 1981, N 2, 16 P.

  摘要：

  DOI：

文献信息

• Benzofurans from Benzophenones and Dimethylacetamide: Copper-Promoted Cascade Formation of Furan O1C2 and C2C3 Bonds Under Oxidative Conditions
  作者：María J. Moure、Raul SanMartin、Esther Dominguez

  DOI：10.1002/anie.201108513

  日期：2012.3.26

  benzofuran core through a cascade of copper‐catalyzed processes wherein the key carbon atom comes from the dimethylacetamide (DMA) solvent. Strong evidence for the participation of a Wacker cyclization catalyzed solely by copper is provided, not only in the title reaction from benzophenones but also from 2‐hydroxy‐α‐arylstyrene derivatives.

  DMA捐赠：乙酸铜（II）和8-羟基喹啉通过一系列铜催化过程来促进苯并呋喃核的形成，其中关键碳原子来自二甲基乙酰胺（DMA）溶剂。有力的证据证明了仅由铜催化的瓦克环化反应不仅在二苯甲酮的标题反应中，而且在2-羟基-α-芳基苯乙烯衍生物的反应中也有提供。
• Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis
  作者：Xin Fan、Huaiyu He、Jiao Li、Guoyong Luo、Yuanyuan Zheng、Jian-Kang Zhou、Juan He、Wenchen Pu、Yun Zhao

  DOI：10.1016/j.bmc.2019.04.028

  日期：2019.6

  Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1) participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5) and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29) as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.
• ROCHE, M.;CERUTTI, E., ANN. SCI. UNIV. BESANCON. CHEM., 1981, N 2, 16 P.
  作者：ROCHE, M.、CERUTTI, E.

  DOI：——

  日期：——