5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol 4-(dihydrogen phosphate) | 1034742-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol 4-(dihydrogen phosphate)
• 英文别名: 3,9,10,11-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepin-4-yl dihydrogen phosphate；(1,2,3,9-tetramethoxy-5,7-dihydrobenzo[d][2]benzoxepin-8-yl) dihydrogen phosphate
• CAS: 1034742-72-7
• 化学式: C₁₈H₂₁O₉P
• 分子量: 412.333
• InChiKey: RNRSBXPQKSZDGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol 4-(dihydrogen phosphate) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.03h， 以99%的产率得到5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol 4-(disodium phosphate)
  参考文献：
  名称：

  Tubulin-binding dibenz[c,e]oxepines: Part 2. Structural variation and biological evaluation as tumour vasculature disrupting agents

  摘要：

  5,7-Dihydro-3,9,10,11-tetramethoxybenz[c,e]oxepin-4-ol 1, prepared from a dibenzyl ether precursor via Pd-catalysed intramolecular direct arylation, possesses broad-spectrum in vitro cytotoxicity towards various tumour cell lines, and induces vascular shutdown, necrosis and growth delay in tumour xenografts in mice at sub-toxic doses. The biological properties of 1 and related compounds can be attributed to their ability to inhibit microtubule assembly at the micromolar level, by binding reversibly to the same site of the tubulin alpha beta-heterodimer as colchicine 2 and the allocolchinol, N-acetylcolchinol 4. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.01.027
• 作为产物：
  描述：

  5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-yl bis(phenylmethyl) phosphate 在 钯 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以to afford 3,9,10,11-tetramethoxy-5,7-dihydrodibenzo[c,e]oxepin-4-yl dihydrogen phosphate as a white crystalline solid (26.6 mg, 97%)的产率得到5,7-dihydro-3,9,10,11-tetramethoxydibenz[c,e]oxepin-4-ol 4-(dihydrogen phosphate)
  参考文献：
  名称：

  Chemical compounds

  摘要：

  描述了一种化合物，其化学式为(I)，其中取代基如文本中所定义，并且该化合物旨在用于在恒温动物中产生血管损伤效应的生产。

  公开号：

  US08178578B2

文献信息

• CHEMICAL COMPOUNDS
  申请人：Wallace Timothy William

  公开号：US20100016261A1

  公开（公告）日：2010-01-21

  A compound of formula (I) is described; wherein the substituents are as defined in the text and wherein the compound is intended for use in the production of a vascular damaging effect in a warm-blooded animal.

  描述了一种化合物，其化学式为（I），其中取代基如文本中所定义，并且该化合物旨在用于在温血动物中产生血管损伤效应的制备。
• Chemical compounds
  申请人：The University of Manchester

  公开号：US08178578B2

  公开（公告）日：2012-05-15

  A compound of formula (I) is described; wherein the substituents are as defined in the text and wherein the compound is intended for use in the production of a vascular damaging effect in a warm-blooded animal.

  描述了一种化合物，其化学式为(I)，其中取代基如文本中所定义，并且该化合物旨在用于在恒温动物中产生血管损伤效应的生产。
• WO2008/75048
  申请人：——

  公开号：——

  公开（公告）日：——
• US8178578B2
  申请人：——

  公开号：US8178578B2

  公开（公告）日：2012-05-15
• Tubulin-binding dibenz[c,e]oxepines: Part 2. Structural variation and biological evaluation as tumour vasculature disrupting agents
  作者：Steven B. Rossington、John A. Hadfield、Steven D. Shnyder、Timothy W. Wallace、Kaye J. Williams

  DOI：10.1016/j.bmc.2017.01.027

  日期：2017.3

  5,7-Dihydro-3,9,10,11-tetramethoxybenz[c,e]oxepin-4-ol 1, prepared from a dibenzyl ether precursor via Pd-catalysed intramolecular direct arylation, possesses broad-spectrum in vitro cytotoxicity towards various tumour cell lines, and induces vascular shutdown, necrosis and growth delay in tumour xenografts in mice at sub-toxic doses. The biological properties of 1 and related compounds can be attributed to their ability to inhibit microtubule assembly at the micromolar level, by binding reversibly to the same site of the tubulin alpha beta-heterodimer as colchicine 2 and the allocolchinol, N-acetylcolchinol 4. (C) 2017 Elsevier Ltd. All rights reserved.