3,4-二氢-11-(4-羟基苯基)-2,2,6,6-四甲基-2H,6H,12H-苯并[1,2-B:3,4-B':5,6-B'']三吡喃-12-酮 | 5745-54-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 3,4-二氢-11-(4-羟基苯基)-2,2,6,6-四甲基-2H,6H,12H-苯并[1,2-B:3,4-B':5,6-B'']三吡喃-12-酮
• 英文名称: 7-(4-hydroxyphenyl)-2,2,10,10-tetramethyl-11,12-dihydro-2H-dipyrano[2,3-f:2',3'-h]chromen-8(10H)-one
• 英文别名: isoosajin；IBS_STOCK1N-12744；3-(4-hydroxy-phenyl)-6,6,10,10-tetramethyl-7,8-dihydro-6H,10H-dipyrano[2,3-f;2',3'-h]chromen-4-one；3-(4-Hydroxy-phenyl)-6,6,10,10-tetramethyl-7,8-dihydro-6H,10H-dipyrano[2,3-f;2',3'-h]chromen-4-on；5-(4-hydroxyphenyl)-10,10,16,16-tetramethyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1,4,7,13,17-pentaen-6-one
• CAS: 5745-54-0
• 化学式: C₂₅H₂₄O₅
• 分子量: 404.463
• InChiKey: FMCWKGDGAHVFMC-UHFFFAOYSA-N

物化性质

• 熔点：
  285℃
• 沸点：
  608.0±55.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-二氢-11-(4-羟基苯基)-2,2,6,6-四甲基-2H,6H,12H-苯并[1,2-B:3,4-B':5,6-B'']三吡喃-12-酮 在 氢氧化钾 、 sodium hydroxide 、 丙酮 、 硫酸二甲酯 作用下， 生成 2-(4-methoxy-phenyl)-1-(5-methoxy-2,2,8,8-tetramethyl-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-6-yl)-ethanone
  参考文献：
  名称：

  欧塞奇橙色颜料；osajin和pomiferin的完整结构。

  摘要：

  DOI：

  10.1021/ja01207a021
• 作为产物：
  描述：

  奥沙京 在 溶剂黄146 作用下， 以75%的产率得到3,4-二氢-11-(4-羟基苯基)-2,2,6,6-四甲基-2H,6H,12H-苯并[1,2-B:3,4-B':5,6-B'']三吡喃-12-酮
  参考文献：
  名称：

  半合成异黄酮作为抗阿尔茨海默氏病的BACE-1抑制剂。

  摘要：

  BACE-1被认为是预防和治疗阿尔茨海默氏病（AD）的靶标之一。我们在这里报告了一类新的半合成的异戊烯基异黄酮衍生物，得自Maclura pomifera的天然类黄酮衍生化。通过人重组BACE-1抑制试验评估了合成化合物的体外抗AD作用。化合物7，8和13被认为是最活跃的候选这表明了计算对接和药代动力学预测之间良好的相关性。此外，细胞毒性研究表明，该化合物对正常和癌细胞系无毒性。在这三种化合物中，化合物7增强A549癌细胞上P-糖蛋白（P-gp）的活性，并增加P-gp ATPase的活性，可能对跨血脑屏障的淀粉样β流出具有作用。总之，本发现可能为发现新型预防和/或治疗AD的化合物铺平道路。

  DOI：

  10.1016/j.bioorg.2019.03.034

文献信息

• Osage Orange Pigments. II. Isolation of a New Pigment, Pomiferin
  作者：M. L. Wolfrom、F. L. Benton、A. S. Gregory、W. W. Hess、J. E. Mahan、P. W. Morgan

  DOI：10.1021/ja01265a079

  日期：1939.10.1
• PRENYLATED ISOFLAVONES FOR TREATMENT OF SUBJECTS WITH MULTIDRUG-RESISTANT CANCER
  申请人：Macau University of Science and Technology

  公开号：US20170151212A1

  公开（公告）日：2017-06-01

  Prenylated isoflavones are suitable to specifically inhibit P-glycoprotein in multidrug-resistant cancer cells leading to an accumulation of cytotoxic compounds or therapeutic compounds in the cells while having exceptionally increased cytotoxic activity specifically towards multidrug-resistant cancer cells and while allowing for an increased activity of chemotherapeutic compounds towards which the cells are resistant. Also in accordance with the present invention is a method for specifically targeting cancer cells with multidrug-resistance as well as a method of potentiating the activity of a chemotherapeutic compound in multidrug-resistant cancer cells. In a further aspect, a kit including a prenylated isoflavone and a chemotherapeutic compound is provided.
• COMPOUNDS AND COMPOSITIONS THAT CAUSE MYCN AND/OR CMYC DEGRADATION AND METHODS OF USE THEREOF
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20220119399A1

  公开（公告）日：2022-04-21

  The present disclosure provides, inter alia, scaffolds and compounds having the structure: Also provided are compositions containing a pharmaceutically acceptable carrier and one or more compounds according to the present disclosure. Further provided are methods for treating or ameliorating the effects of a cancer in a subject, methods for selectively killing a cancer cell, methods of modulating mTORC1/2 signaling activity in a cell, methods of modulating the activity of a Master Regulator for MycN in a subject having MycN-amplified neuroblastoma (MycN AMP NBL), methods of selectively treating or ameliorating effects of a cancer in a subject in need thereof, and platforms and methods for identifying a compound that induces degradation of a cancer-related protein. Also provided are kits comprising a compound or a pharmaceutical composition according to the present disclosure. Methods for treating cancers and methods for modulating MYC Master Regulators using other compounds are also provided.
• US9974766B2
  申请人：——

  公开号：US9974766B2

  公开（公告）日：2018-05-22
• Osage Orange Pigments. XI. Complete Structures of Osajin and Pomiferin¹
  作者：M. L. Wolfrom、Walter D. Harris、George F. Johnson、J. E. Mahan、Sam M. Moffett、Bernard Wildi

  DOI：10.1021/ja01207a021

  日期：1946.3