2-(furan-3-ylmethylene)benzofuran-3(2H)-one | 1510838-61-5

• 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-(furan-3-ylmethylene)benzofuran-3(2H)-one
• CAS: 1510838-61-5
• 化学式: C₁₃H₈O₃
• 分子量: 212.205
• InChiKey: KPXUEVUIYZUXMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(furan-3-ylmethylene)benzofuran-3(2H)-one 、 1-(2-furan-2-yl-2-oxo-ethyl)-pyridinium iodide 在 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 反应 16.0h， 以6.5%的产率得到2-(furan-2-yl)-4-(furan-3-yl)benzofuro[3,2-b]pyridine
  参考文献：
  名称：

  2,4-二芳基苯并呋喃[3,2-b]吡啶衍生物：拓扑异构酶抑制活性和细胞毒性的设计、合成和评价

  摘要：

  对设计和合成的 24 种 2,4-二芳基苯并呋喃 [3,2-b] 吡啶衍生物的拓扑异构酶 I 和 II 抑制活性以及对几种人类癌细胞系的细胞毒性进行了评估。各种芳基如苯基、2-或3-呋喃基、2-或3-噻吩基和2-吡啶基在中心吡啶的2-或4-位被取代。化合物 8、12、13 和 14，在中心吡啶的 2 位或 4 位具有 2-呋喃基，在 100°C 时显示出显着的拓扑异构酶 II 抑制活性。

  DOI：

  10.5012/bkcs.2013.34.10.3073
• 作为产物：
  描述：

  3-糠醛 、 3-苯并呋喃酮 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 以52.7%的产率得到2-(furan-3-ylmethylene)benzofuran-3(2H)-one
  参考文献：
  名称：

  6-羟基-苯并呋喃-3-（2H）-酮作为潜在的抗炎剂：LPS刺激的RAW 264.7巨噬细胞中ROS的合成和抑制活性

  摘要：

  在RAW 264.7巨噬细胞中表现出LPS刺激的6-羟基-苯并呋喃-3-（2H）-酮

  DOI：

  10.1002/bkcs.12215

文献信息

• 2-Chlorophenyl-substituted benzofuro[3,2-b]pyridines with enhanced topoisomerase inhibitory activity: The role of the chlorine substituent
  作者：Til Bahadur Thapa Magar、Tara Man Kadayat、Hwa-Jong Lee、Seojeong Park、Ganesh Bist、Aarajana Shrestha、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.bmcl.2017.06.025

  日期：2017.8

  A new series of 2-chloropheny-substituted benzofuro[3,2-b]pyridines were designed, synthesized, and evaluated for topoisomerase I and II inhibition and antiproliferative activity. Compounds 17–19, 23, 24, 26, and 27 exhibited excellent topo II inhibitory activity. A systematic structure-activity relationship study revealed the important role of chlorine substitution in the strong topoisomerase inhibitory

  设计，合成了一系列新的2-氯苯基取代的苯并呋喃[3,2- b ]吡啶，并对其拓扑异构酶I和II的抑制作用和抗增殖活性进行了评估。化合物17 - 19，23，24，26，和27显示出优异的拓扑异构酶II的抑制活性。一项系统的结构-活性关系研究表明，氯取代在强大的拓扑异构酶抑制活性中具有重要作用。
• I₂/FeCl₃-Catalyzed Domino Reaction of Aurones with Enamino Esters for the Synthesis of Highly Functionalized Pyrroles
  作者：Hui Xu、Ming-Jun Li、Hong Chen、Fei-Hong Huang、Qi-Yue Zhu、Guan-Wu Wang、Ze Zhang

  DOI：10.1021/acs.orglett.2c03537

  日期：2022.11.18

  A novel and efficient I2/FeCl3-catalyzed domino reaction of aurones with enamino esters via Michael addition, iodination, intramolecular nucleophilic substitution, and spiro ring opening processes has been developed, affording a vast variety of polysubstituted pyrroles in moderate to excellent yields. This protocol features mild reaction conditions, broad substrate scope, high atom economy and efficiency

  已开发出一种新颖且高效的 I 2 /FeCl 3催化的金酮与烯胺酯的多米诺反应，通过迈克尔加成、碘化、分子内亲核取代和螺环开环过程，以中等至优异的收率提供多种多取代吡咯。该方案具有反应条件温和、底物范围广、原子经济性和效率高以及大规模合成的可行性等特点。提出了一种可能的吡咯合成机理。
• A Series of Novel Terpyridine-Skeleton Molecule Derivants Inhibit Tumor Growth and Metastasis by Targeting Topoisomerases
  作者：Han-Byeol Kwon、Chanmi Park、Kyung-Hwa Jeon、Eunyoung Lee、So-Eun Park、Kyu-Yeon Jun、Tara Man Kadayat、Pritam Thapa、Radha Karki、Younghwa Na、Mi Sun Park、Seung Bae Rho、Eung-Seok Lee、Youngjoo Kwon

  DOI：10.1021/jm501023q

  日期：2015.2.12

  A series of novel terpyridine-skeleton molecules containing conformational rigidity, 14 containing benzo[4,5]furo[3,2-b]pyridine core and 15 comprising chromeno[4,3-b]pyridine core, were synthesized, and their biological activities were evaluated. 3-(4-Phenylbenzo[4,5]furo[3,2-b]pyridin-2-yl)phenol (8) was determined to be a nonintercalative topo I and II dual catalytic inhibitor and 3-(4-phenylchromeno[4,3-b]pyridine-2-yl)phenol (22) was determined to be a nonintercalative topo II alpha specific catalytic inhibitor by various assays. These two catalytic inhibitors induced apoptosis in addition to G1 arrest in T47D human breast cancer cells with much less DNA toxicity than etoposide. Compounds 8 and 22 significantly inhibited tumor growth in HCT15 subcutaneously implanted xenografted mice. The modification of compounds 8 and 22 with the introduction of a methoxy instead of a hydroxy group enhanced endogenous topo inhibitory activity, metabolic stability in diverse types of liver microsomes and improved pharmacokinetic parameters in rat plasma such as augmentation of bioavailability (41.3% and 33.2% for 2-(3-methoxyphenyl)-4-phenylbenzofuro[3,2-b]pyridine (8-M) and 3-(4-phenylchromeno[4,3-b]pyridine-2-yl)methoxybenzene (22-M), respectively).