3-(furan-3-ylmethylidene)chromen-4-one | 170696-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(furan-3-ylmethylidene)chromen-4-one
• CAS: 170696-58-9
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: ZBOIIAKPRQREGW-UHFFFAOYSA-N

物化性质

• 沸点：
  395.4±42.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-(furan-3-ylmethylidene)chromen-4-one 、 1-[2-oxo-2-(thiophen-2-yl)ethyl]pyridinium iodide 在 ammonium acetate 、 溶剂黄146 作用下， 以32.4%的产率得到4-(furan-3-yl)-2-(thiophen-2-yl)-5H-chromeno[4,3-b]pyridine
  参考文献：
  名称：

  Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship

  摘要：

  Designed and synthesized were a series of 5H-chromeno[4,3-b]pyridines with substitution at 2- and 4-positions with various 5- or 6-membered heteroaromatics as antitumor agents. They were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Structure activity relationship study showed that 2-furyl or 2-thienyl at 2- or 4-position of central pyridine is crucial in displaying topo I or II inhibitory activity and cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.029
• 作为产物：
  描述：

  3-糠醛 、 2,3-二氢苯并吡喃-4-酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3-(furan-3-ylmethylidene)chromen-4-one
  参考文献：
  名称：

  Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship

  摘要：

  Designed and synthesized were a series of 5H-chromeno[4,3-b]pyridines with substitution at 2- and 4-positions with various 5- or 6-membered heteroaromatics as antitumor agents. They were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Structure activity relationship study showed that 2-furyl or 2-thienyl at 2- or 4-position of central pyridine is crucial in displaying topo I or II inhibitory activity and cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.029

文献信息

• 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).
• 2,4-Diaryl-5H-chromeno [4,3-b]pyridines: Synthesis, Topoisomerase I and II Inhibitory Activity, and Cytotoxicity
  作者：Pritam Thapa、Eung-Seok Lee

  DOI：10.5012/bkcs.2012.33.9.3103

  日期：2012.9.20
• Synthesis of 2,4-diaryl chromenopyridines and evaluation of their topoisomerase I and II inhibitory activity, cytotoxicity, and structure–activity relationship
  作者：Uttam Thapa、Pritam Thapa、Radha Karki、Minho Yun、Jae Hun Choi、Yurngdong Jahng、Eunyoung Lee、Kyung-Hwa Jeon、Younghwa Na、Eun-Mi Ha、Won-Jea Cho、Youngjoo Kwon、Eung-Seok Lee

  DOI：10.1016/j.ejmech.2011.04.029

  日期：2011.8

  Designed and synthesized were a series of 5H-chromeno[4,3-b]pyridines with substitution at 2- and 4-positions with various 5- or 6-membered heteroaromatics as antitumor agents. They were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Structure activity relationship study showed that 2-furyl or 2-thienyl at 2- or 4-position of central pyridine is crucial in displaying topo I or II inhibitory activity and cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.