2-(4-hydroxybenzylidene)benzofuran-3(2H)-one | 24389-48-8

• 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-(4-hydroxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 2-[(4-Hydroxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 24389-48-8
• 化学式: C₁₅H₁₀O₃
• mdl: MFCD02326346
• 分子量: 238.243
• InChiKey: BAYNHPXTNUSVIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  238-239 °C
• 沸点：
  435.6±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-(4-hydroxybenzylidene)benzofuran-3(2H)-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 2-(4-hydroxybenzyl)benzofuran-3(2H)-one
  参考文献：
  名称：

  通过开环氟化贝克曼断裂策略合成氟醚

  摘要：

  开发了一种单氟醚的S N 1 型氟化方法。该反应的关键是由氧辅助贝克曼断裂驱动的氟化 C-C 键断裂。为了实现这种转化，研究了由 3-香豆酮和 1-茚满酮衍生的环状 α-芳氧基肟作为底物，使用N , N-二乙基氨基三氟化硫 (DAST) 作为肟活化剂和氟化物供体的双重作用试剂。该方法的特点是合成未开发的化学基序，操作条件简单温和。

  DOI：

  10.1021/acs.orglett.3c02343
• 作为产物：
  描述：

  2’,4-二羟基查耳酮 在 吡啶 、 mercury(II) diacetate 作用下， 反应 1.0h， 以35%的产率得到2-(4-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

• 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。
• Inhibition of prostaglandin E2 production by synthetic minor prenylated chalcones and flavonoids: Synthesis, biological activity, crystal structure, and in silico evaluation
  作者：Kamal Rullah、Mohd Fadhlizil Fasihi Mohd Aluwi、Bohari M. Yamin、Mohd Nazri Abdul Bahari、Leong Sze Wei、Syahida Ahmad、Faridah Abas、Nor Hadiani Ismail、Ibrahim Jantan、Lam Kok Wai

  DOI：10.1016/j.bmcl.2014.06.061

  日期：2014.8

  The discovery of potent inhibitors of prostaglandin E2 (PGE2) synthesis in recent years has been proven to be an important game changer in pharmaceutical industry. It is known that excessive production of PGE2 triggers a vast array of biological signals and physiological events that contributes to inflammatory diseases such as rheumatoid arthritis, atherosclerosis, cancer, and pain. In this Letter, we report the synthesis of a series of minor prenylated chalcones and flavonoids which was found to be significantly active in suppressing the PGE2 production secreted by lipopolysaccharide-induced mouse macrophage cells (RAW 264.7). Among the compounds tested, 14b showed a dose-response inhibition of PGE2 production with an IC50 value of 2.1 μM. The suppression upon PGE2 secretion was not due to cell death since 14b did not reduce the cell viability in close proximity to the PGE2 inhibition concentration. The obtained atomic coordinates for the single-crystal XRD of 14b was then applied in the docking simulation to determine the potential important binding interactions with murine COX-2 and mPGES-1 putative binding sites.
• Hydrogel-Encapsulated Biofilm Inhibitors Abrogate the Cariogenic Activity of <i>Streptococcus mutans</i>
  作者：Parmanand Ahirwar、Veronika Kozlovskaya、Bhavitavya Nijampatnam、Edwin M. Rojas、Piyasuda Pukkanasut、Daniel Inman、Maksim Dolmat、Anna C. Law、Norbert Schormann、Champion Deivanayagam、Gregory J. Harber、Suzanne M. Michalek、Hui Wu、Eugenia Kharlampieva、Sadanandan E. Velu

  DOI：10.1021/acs.jmedchem.3c00272

  日期：2023.6.22
• 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.