2-((3,5-dibromo-4-hydroxyphenethyl)amino)naphthalene-1,4-dione | 123475-75-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-((3,5-dibromo-4-hydroxyphenethyl)amino)naphthalene-1,4-dione
• 英文别名: 2-{[2-(3,5-Dibromo-4-hydroxyphenyl)ethyl]amino}naphthoquinone；2-[2-(3,5-dibromo-4-hydroxyphenyl)ethylamino]naphthalene-1,4-dione
• CAS: 123475-75-2
• 化学式: C₁₈H₁₃Br₂NO₃
• 分子量: 451.114
• InChiKey: NVRCNBYIOHZECJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((3,5-dibromo-4-hydroxyphenethyl)amino)naphthalene-1,4-dione 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 生成 2',6'-dibromospiro[2,3-dihydro-1H-benzo[g]quinoline-4,4'-cyclohexa-2,5-diene]-1',5,10-trione
  参考文献：
  名称：

  Discorhabdin生物碱的合成方法：取代的苯酚衍生物的高价碘氧化为氮杂碳环螺二烯酮

  摘要：

  在2,2,2-三氟乙醇中，苯基碘基双（三氟乙酸盐）（PIFA）将甲硅烷基化的取代酚进行高价碘氧化，制得的氮杂碳环螺二烯酮具有良好的收率。

  DOI：

  10.1016/s0040-4039(01)80375-0
• 作为产物：
  描述：

  酪胺盐酸盐 在 溴 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 生成 2-((3,5-dibromo-4-hydroxyphenethyl)amino)naphthalene-1,4-dione
  参考文献：
  名称：

  Ezrin inhibitors and methods of making and using

  摘要：

  该发明涵盖了包含以下化合物的化合物和药物组合物（I）的药物组合物，或其药用盐或前药，这些化合物对于抑制细胞中的ezrin蛋白或抑制癌细胞的生长是有用的。

  公开号：

  US09522908B2

文献信息

• Design, synthesis and biological evaluation of ezrin inhibitors targeting metastatic osteosarcoma
  作者：Mikell Paige、George Kosturko、Güllay Bulut、Matthew Miessau、Said Rahim、Jeffrey A. Toretsky、Milton L. Brown、Aykut Üren

  DOI：10.1016/j.bmc.2013.11.003

  日期：2014.1

  Respiratory failure due to pulmonary metastasis is the major cause of death for patients with osteosarcoma. However, the molecular basis for metastasis of osteosarcoma is poorly understood. Recently, ezrin, a member of the ERM family of proteins, has been associated with osteosarcoma metastasis to the lungs. The small molecule NSC 668394 was identified to bind to ezrin, inhibit in vitro and in vivo cell migration, invasion, and metastatic colony survival. Reported herein are the design and synthesis of analogues of NSC 668394, and subsequent functional ezrin inhibition studies. The binding affinity was characterized by surface plasmon resonance technique. Cell migration and invasion activity was determined by electrical cell impedance methodology. Optimization of a series of heterocyclic-dione analogues led to the discovery of compounds 21k and 21m as potential novel antimetastatic agents. (C) 2013 Elsevier Ltd. All rights reserved.
• KITA, YASUYUKI;YAKURA, TAKAYUKI;TOHMA, HIROFUMI;KIKUCHI, KAZUMI;TAMURA, Y+, TETRAHEDRON LETT., 30,(1989) N, C. 1119-1120
  作者：KITA, YASUYUKI、YAKURA, TAKAYUKI、TOHMA, HIROFUMI、KIKUCHI, KAZUMI、TAMURA, Y+

  DOI：——

  日期：——
• NOVEL EZRIN INHIBITORS AND METHODS OF MAKING AND USING
  申请人：GEORGETOWN UNIVERSITY

  公开号：US20140135325A1

  公开（公告）日：2014-05-15

  The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growth of a cancer cell.
• Novel Ezrin Inhibitors and Methods of Making and Using
  申请人：Georgetown University

  公开号：US20180148437A1

  公开（公告）日：2018-05-31

  The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growh of a cancer cell.
• US9522908B2
  申请人：——

  公开号：US9522908B2

  公开（公告）日：2016-12-20