1-nitro-phenanthrene-9,10-dione | 109504-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-nitro-phenanthrene-9,10-dione
• 英文别名: 1-Nitro-phenanthren-9,10-dion；Nitrophenanthrene-9,10-quinone；1-nitrophenanthrene-9,10-dione
• CAS: 109504-22-5
• 化学式: C₁₄H₇NO₄
• 分子量: 253.214
• InChiKey: YZUGWKNDIVSZKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-nitro-phenanthrene-9,10-dione 在 镍 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 1-amino-phenanthrene-9,10-dione
  参考文献：
  名称：

  Potent Reversible Inhibitors of the Protein Tyrosine Phosphatase CD45

  摘要：

  The cytosolic portion of CD45, a major transmembrane glycoprotein found on nucleated hematopoietic cells, contains protein tyrosine phosphatase activity and is critical for T-cell receptor-mediated T-cell activation. CD45 inhibitors could have utility in the treatment of autoimmune disorders and organ graft rejection. A number of 9, l0-phenanthrenediones were identified that reversibly inhibited CD45-mediated p-nitrophenyl phosphate (pNPP) hydrolysis. Chemistry efforts around the 9,10-phenanthrenedione core led to the most potent inhibitors known to date. In a functional assay, the compounds were also potent inhibitors of T-cell receptor-mediated proliferation, with activities in the low micromolar range paralleling their enzyme inhibition. It was also discovered that the nature of modification to the phenanthrenedione pharmacophore could affect selectivity for CD45 over PTP1B (protein tyrosine phosphatase 1B) or vice versa.

  DOI：

  10.1021/jm000447i
• 作为产物：
  描述：

  9-bromo-8-nitro-phenanthrene 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 1-nitro-phenanthrene-9,10-dione
  参考文献：
  名称：

  Braithwaite; Holt, Journal of the Chemical Society, 1959, p. 2304

  摘要：

  DOI：

文献信息

• Triarylmethane dyes
  申请人：——

  公开号：US20030181740A1

  公开（公告）日：2003-09-25

  Described is a triarylmethane dye of the formula I where R 1 and R 2 are independently methyl, ethyl or hydroxyethyl, Q is substituted or unsubstituited phenyl or naphthyl and A ⊖ is the equivalent of an anion. It does not detach carcinogenic Michler's ketone. 1
• US6846956B2
  申请人：——

  公开号：US6846956B2

  公开（公告）日：2005-01-25
• Potent Reversible Inhibitors of the Protein Tyrosine Phosphatase CD45
  作者：Rebecca A. Urbanek、Suzanne J. Suchard、Gary B. Steelman、Katharine S. Knappenberger、Linda A. Sygowski、Chris A. Veale、Marc J. Chapdelaine

  DOI：10.1021/jm000447i

  日期：2001.5.1

  The cytosolic portion of CD45, a major transmembrane glycoprotein found on nucleated hematopoietic cells, contains protein tyrosine phosphatase activity and is critical for T-cell receptor-mediated T-cell activation. CD45 inhibitors could have utility in the treatment of autoimmune disorders and organ graft rejection. A number of 9, l0-phenanthrenediones were identified that reversibly inhibited CD45-mediated p-nitrophenyl phosphate (pNPP) hydrolysis. Chemistry efforts around the 9,10-phenanthrenedione core led to the most potent inhibitors known to date. In a functional assay, the compounds were also potent inhibitors of T-cell receptor-mediated proliferation, with activities in the low micromolar range paralleling their enzyme inhibition. It was also discovered that the nature of modification to the phenanthrenedione pharmacophore could affect selectivity for CD45 over PTP1B (protein tyrosine phosphatase 1B) or vice versa.
• Braithwaite; Holt, Journal of the Chemical Society, 1959, p. 2304
  作者：Braithwaite、Holt

  DOI：——

  日期：——