2-(2-hydroxybenzylidene)benzofuran-3(2H)-one | 112980-30-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: 2-(2-hydroxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 2-[(2-Hydroxyphenyl)methylidene]-1-benzofuran-3(2H)-one；2-[(2-hydroxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 112980-30-0
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: TVCLXWLVYCIOMW-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C
• 沸点：
  437.2±45.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxybenzylidene)benzofuran-3(2H)-one 、 1-[2-(4-chloro-phenyl)-2-oxo-ethyl]-pyridinium iodide 在 ammonium acetate 、 溶剂黄146 作用下， 以30.4%的产率得到2-(2-(4-chlorophenyl)benzofuro[3,2-b]pyridin-4-yl)phenol
  参考文献：
  名称：

  新型2,4-氯和羟基取代的二苯基苯并呋喃[3,2- b ]吡啶的合理设计，合成和评价：非插入式催化拓扑异构酶I和II双重抑制剂

  摘要：

  构象约束的2,4-氯-和羟基取代的二苯基苯并呋喃[3,2- b]系列新化合物对吡啶进行了合理设计和合成。对它们的生物学活性进行了拓扑异构酶I和II抑制活性的评估，以及针对几种人类癌细胞系的抗增殖活性，以开发新型抗癌剂。在中央吡啶的4-位上具有酚部分的大多数化合物在低微摩尔范围内表现出显着的双重拓扑异构酶I和II双重抑制活性，以及​​强的抗增殖活性。结构活性关系研究表明，中央吡啶4位的酚部分，与中央吡啶2位的氯苯基部分无关，在双重拓扑异构酶抑制活性和抗增殖活性中都起着重要作用。用于化合物14的作用方式研究我们展示了对HCT15细胞最强的双重拓扑异构酶I和II抑制活性和抗增殖活性，我们进行了可裂解的复合物测定，谱带耗竭测定，彗星测定和竞争性EtBr置换测定。化合物14用作非插入式催化拓扑I和II双重抑制剂。另外，化合物14通过增加Bax，减少Bcl-2和增加PARP裂解来诱导HCT15细胞凋亡。

  DOI：

  10.1016/j.ejmech.2017.01.003
• 作为产物：
  描述：

  2,2-二羟基查尔酮 在 吡啶 、 mercury(II) diacetate 作用下， 反应 1.0h， 以40%的产率得到2-(2-hydroxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

  摘要：

  A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non -selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki = 0.10 +/- 0.01 mu mol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki = 0.12 0.01 p.mol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.02.009

文献信息

• A structural optimized fluorescent probe for monitoring hydrogen sulfide in cells and zebrafish
  作者：Meng-Ya Guo、Yun-Zhang Li、Xiao-Jing Liu、Bao-Zhong Wang、Yu-Shun Yang、Hai-Liang Zhu

  DOI：10.1016/j.saa.2023.123763

  日期：2024.3
• Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives
  作者：Vishnu Nayak Badavath、Chandrani Nath、Narayana Murthy Ganta、Gulberk Ucar、Barij Nayan Sinha、Venkatesan Jayaprakash

  DOI：10.1016/j.cclet.2017.02.009

  日期：2017.7

  A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non -selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki = 0.10 +/- 0.01 mu mol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki = 0.12 0.01 p.mol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
• Rational design, synthesis, and evaluation of novel 2,4-Chloro- and Hydroxy-Substituted diphenyl Benzofuro[3,2-b]Pyridines: Non-intercalative catalytic topoisomerase I and II dual inhibitor
  作者：Seojeong Park、Til Bahadur Thapa Magar、Tara Man Kadayat、Hwa Jong Lee、Ganesh Bist、Aarajana Shrestha、Eung-Seok Lee、Youngjoo Kwon

  DOI：10.1016/j.ejmech.2017.01.003

  日期：2017.2

  action for compound 14 which displayed the most strong dual topoisomerase I and II inhibitory activity and antiproliferative activity against HCT15 cell, we performed cleavable complex assay, band depletion assay, comet assay, and competitive EtBr displacement assay. Compound 14 functioned as non-intercalative catalytic topo I and II dual inhibitor. In addition, compound 14 induced apoptosis in HCT15 cells

  构象约束的2,4-氯-和羟基取代的二苯基苯并呋喃[3,2- b]系列新化合物对吡啶进行了合理设计和合成。对它们的生物学活性进行了拓扑异构酶I和II抑制活性的评估，以及针对几种人类癌细胞系的抗增殖活性，以开发新型抗癌剂。在中央吡啶的4-位上具有酚部分的大多数化合物在低微摩尔范围内表现出显着的双重拓扑异构酶I和II双重抑制活性，以及​​强的抗增殖活性。结构活性关系研究表明，中央吡啶4位的酚部分，与中央吡啶2位的氯苯基部分无关，在双重拓扑异构酶抑制活性和抗增殖活性中都起着重要作用。用于化合物14的作用方式研究我们展示了对HCT15细胞最强的双重拓扑异构酶I和II抑制活性和抗增殖活性，我们进行了可裂解的复合物测定，谱带耗竭测定，彗星测定和竞争性EtBr置换测定。化合物14用作非插入式催化拓扑I和II双重抑制剂。另外，化合物14通过增加Bax，减少Bcl-2和增加PARP裂解来诱导HCT15细胞凋亡。