5-nitronaphthostyril | 65300-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-nitronaphthostyril
• 英文别名: 5-Nitrobenzo[cd]indol-2(1H)-one；5-nitro-1H-benzo[cd]indol-2-one
• CAS: 65300-69-8
• 化学式: C₁₁H₆N₂O₃
• 分子量: 214.18
• InChiKey: HEUWZZPNLPASHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-nitronaphthostyril 、 乙酸酐 在 sodium acetate 作用下， 生成 1-acetyl-5-nitro-1H-benz[cd]indol-2-one
  参考文献：
  名称：

  Corbellini; Fossati, Rendiconti - Istituto Lombardo Accademia di Scienze e Lettere, A: Scienze Matematiche, Fisiche, Chimiche e Geologiche, 1936, vol. 69, p. 258,272

  摘要：

  DOI：
• 作为产物：
  描述：

  N-Hydroxy-4-nitronaphthalimid 在 sodium hydroxide 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 17.0h， 生成 5-nitronaphthostyril
  参考文献：
  名称：

  Crystal-structure-based design and synthesis of benz[cd]indole-containing inhibitors of thymidylate synthase

  摘要：

  The X-ray crystal-structure-based design, synthesis, and biological activity of a novel family of benz[cd]indole-containing inhibitors of thymidylate synthase (TS) are described. The structure-activity of the lead compound was studied by conceptually dividing the molecule into four regions and independently optimizing the substituents for each region. Combination of favored substituents for each region led to inhibitors with K(i)'s against the human enyzme in the range of 10-20 nM. Thymidine shift experiments suggested that the cytotoxic properties of the best enzyme inhibitors were due to TS targeting in cells. The inhibitors were synthesized from substitued 6-aminobenz[cd]indol-2(1H)-ones by alkylation with both a simple alkyl group and a substituted benzylic portion. The 2,6-diaminobenz[cd]indoles were prepared from the corresponding lactams by conversion to the thiolactam, alkylation to the methylated thiolactam, and then displacement with a substituted or unsubstituted amine.

  DOI：

  10.1021/jm00082a006

文献信息

• Novel antitumor agent family of 1H-benzo[c,d]indol-2-one with flexible basic side chains: Synthesis and biological evaluation
  作者：Hong Yin、Yufang Xu、Xuhong Qian

  DOI：10.1016/j.bmc.2006.11.016

  日期：2007.2.1

  A series of mono-1H-benzo[c,d]indol-2-one with different amine side chains and bis-1H-benzo[c,d]indol-2-one as novel family of DNA intercalators were designed and synthesized, the contributions of aromatic chromophores and amine side chains for DNA binding properties, for example, intercalation and electrostatic binding, respectively, were evaluated. Among them, A3 tailed with N,N-dimethylamino-ethyl-ethane-1,2-diamine showed selective anti-tumor activities against cell lines A549 and P388 with IC50 0.428 mu m and 1.69 mu m. (c) 2006 Elsevier Ltd. All rights reserved.
• Corbellini; Fossati, Rendiconti - Istituto Lombardo Accademia di Scienze e Lettere, A: Scienze Matematiche, Fisiche, Chimiche e Geologiche, 1936, vol. 69, p. 258,271
  作者：Corbellini、Fossati

  DOI：——

  日期：——
• BYSTRITSKIJ G. I.; OVSYANNIKOVA S. V., ZH. ORGAN. XIMII, 1979, 15, HO 12, 2577-2581
  作者：BYSTRITSKIJ G. I.、 OVSYANNIKOVA S. V.

  DOI：——

  日期：——
• PLAKSIDIN V. L.; BOCTPOBA V. N.; GNATYUK P. P.; ZADOROZHNYJ N. M., ZH. ORGAN XIMII, 1977, 13, HO 10, 2194-2202
  作者：PLAKSIDIN V. L.、 BOCTPOBA V. N.、 GNATYUK P. P.、 ZADOROZHNYJ N. M.

  DOI：——

  日期：——
• US4146541A
  申请人：——

  公开号：US4146541A

  公开（公告）日：1979-03-27