(5-chlorobenzofuran-2-yl)(phenyl)methanol

• 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-chlorobenzofuran-2-yl)(phenyl)methanol
• 英文别名: (5-Chloro-1-benzofuran-2-yl)-phenylmethanol
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: FIUREYXUADESFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-甲基吲哚 、 (5-chlorobenzofuran-2-yl)(phenyl)methanol 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以124 mg的产率得到2-((5-chlorobenzofuran-2-yl)(phenyl)methyl)-3-methyl-1H-indole
  参考文献：
  名称：

  Discovery of 3-(benzofuran-2-ylmethyl)-1H-indole derivatives as potential autophagy inducers in cervical cancer cells

  摘要：

  In this manuscript we have documented the identification of a novel anticancer scaffold 3-(benzofuran-2-yl-methyl)-1H-indole. This scaffold has been designed by tweaking the known bisindolylmethane scaffold of natural products that display a wide range of biological activities. A series of 24 new conjugates have been synthesized and among them 5 derivatives exhibited IC50 values less than 40 mu M against two cervical cancer cell lines SiHa and C33a. Further mechanistic studies of two compounds 3eb and 3ec revealed that the toxicity of these compounds was due to the effective induction of autophagy mediated cell death. The autophagy induction was confirmed by the progressive conversion of LC3I to LC3II and downregulation of p62 in cervical cancer cells.

  DOI：

  10.1016/j.bmcl.2020.127431
• 作为产物：
  描述：

  (5-氯-1-苯并呋喃-2-基)-苯基甲酮 在 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 联硼酸频那醇酯 、 copper(I) bromide 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以76%的产率得到(5-chlorobenzofuran-2-yl)(phenyl)methanol
  参考文献：
  名称：

  铜（I）催化多米诺-硼基化-原脱硼策略将苯并呋喃-2-基酮与B 2销2还原为醇。

  摘要：

  开发了一种新型的铜（I）催化的具有B 2 pin 2的呋喃环上苯并呋喃-2-基酮的羰基化学选择性还原。该反应在温和的条件下进行。获得了高价值的苯并呋喃仲醇衍生物，具有良好的收率和优异的收率，具有广泛的底物范围。机理研究表明该反应涉及多米诺骨化-硼氢化-原脱硼途径。

  DOI：

  10.1021/acs.joc.7b00596

文献信息

• (Benzofuran-2-yl)imidazoles having pharmaceutical activity, their salts and relevant production processes
  申请人：A. MENARINI INDUSTRIE FARMACEUTICHE RIUNITE S.R.L.

  公开号：EP0257171B1

  公开（公告）日：1990-08-29
• US4800208A
  申请人：——

  公开号：US4800208A

  公开（公告）日：1989-01-24
• Copper(I)-Catalyzed Chemoselective Reduction of Benzofuran-2-yl Ketones to Alcohols with B₂pin₂ via a Domino-Borylation-Protodeboronation Strategy
  作者：Qingqing Xuan、Weiguang Kong、Qiuling Song

  DOI：10.1021/acs.joc.7b00596

  日期：2017.7.21

  A novel copper(I)-catalyzed chemoselective reduction of the carbonyls of benzofuran-2-yl ketones over furan rings with B2pin2 has been developed. This reaction proceeded under mild conditions. High valuable secondary alcohol derivatives of benzofurans were obtained in good to excellent yields with a broad substrate scope. The mechanistic studies suggested that a domino-borylation-protodeboronation

  开发了一种新型的铜（I）催化的具有B 2 pin 2的呋喃环上苯并呋喃-2-基酮的羰基化学选择性还原。该反应在温和的条件下进行。获得了高价值的苯并呋喃仲醇衍生物，具有良好的收率和优异的收率，具有广泛的底物范围。机理研究表明该反应涉及多米诺骨化-硼氢化-原脱硼途径。
• Discovery of 3-(benzofuran-2-ylmethyl)-1H-indole derivatives as potential autophagy inducers in cervical cancer cells
  作者：Shaziyaparveen K. Siddiqui、Vinodh J. SahayaSheela、Srinivas Kolluru、Ganesh N. Pandian、Thankayyan R. Santhoshkumar、Vipin M. Dan、Chepuri V. Ramana

  DOI：10.1016/j.bmcl.2020.127431

  日期：2020.10

  In this manuscript we have documented the identification of a novel anticancer scaffold 3-(benzofuran-2-yl-methyl)-1H-indole. This scaffold has been designed by tweaking the known bisindolylmethane scaffold of natural products that display a wide range of biological activities. A series of 24 new conjugates have been synthesized and among them 5 derivatives exhibited IC50 values less than 40 mu M against two cervical cancer cell lines SiHa and C33a. Further mechanistic studies of two compounds 3eb and 3ec revealed that the toxicity of these compounds was due to the effective induction of autophagy mediated cell death. The autophagy induction was confirmed by the progressive conversion of LC3I to LC3II and downregulation of p62 in cervical cancer cells.