4-anilino-3-nitro-1,8-naphthalic anhydride | 120228-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-anilino-3-nitro-1,8-naphthalic anhydride
• 英文别名: 5-nitro-6-(phenylamino)-1H,3H-benzo[de]isochromene-1,3-dione；8-anilino-7-nitro-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-2,4-dione
• CAS: 120228-35-5
• 化学式: C₁₈H₁₀N₂O₅
• 分子量: 334.288
• InChiKey: GJZDWAAXGWCLEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-anilino-3-nitro-1,8-naphthalic anhydride 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 24.0h， 以65%的产率得到5-Oxa-8,13-diaza-benzo[de]naphthacene-4,6-dione
  参考文献：
  名称：

  Novel synthetic isoquinolino[5,4-ab]phenazines: Inhibition toward topoisomerase I, antitumor and DNA photo-cleaving activities

  摘要：

  The novel DNA interactive isoquinolino[5,4-ab]phenazine derivatives were designed and synthesized. Their inhibitory abilities toward topoisomerase 1, antitumor activities and DNA photo-cleaving abilities were examined. The substituents at peri sites of two phenazine N atoms played very important roles for all these biological activities. At a concentration of 100 mu M, all these phenazine derivatives (but A2 and A6) exhibited an inhibitory activity toward topoisomerase I. A6 had efficient antitumor activities against both human lung cancer cell (A549) and murine leukemia cell (P388). A1, A5, and A6 exhibited antitumor activities selectively only against P388. A2 was the most efficient DNA photocleaver, which had converted supercoiled DNA from form I to form II at < 1 mu M. Under anaerobic conditions, the electron transfer mechanism mainly contributed to DNA photo-induced cleavage, while under aerobic conditions, superoxide anion was also involved in this process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.029
• 作为产物：
  描述：

  4-溴-3-硝基-1,8-萘酐 、 苯胺 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以85%的产率得到4-anilino-3-nitro-1,8-naphthalic anhydride
  参考文献：
  名称：

  Novel synthetic isoquinolino[5,4-ab]phenazines: Inhibition toward topoisomerase I, antitumor and DNA photo-cleaving activities

  摘要：

  The novel DNA interactive isoquinolino[5,4-ab]phenazine derivatives were designed and synthesized. Their inhibitory abilities toward topoisomerase 1, antitumor activities and DNA photo-cleaving abilities were examined. The substituents at peri sites of two phenazine N atoms played very important roles for all these biological activities. At a concentration of 100 mu M, all these phenazine derivatives (but A2 and A6) exhibited an inhibitory activity toward topoisomerase I. A6 had efficient antitumor activities against both human lung cancer cell (A549) and murine leukemia cell (P388). A1, A5, and A6 exhibited antitumor activities selectively only against P388. A2 was the most efficient DNA photocleaver, which had converted supercoiled DNA from form I to form II at < 1 mu M. Under anaerobic conditions, the electron transfer mechanism mainly contributed to DNA photo-induced cleavage, while under aerobic conditions, superoxide anion was also involved in this process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.029

文献信息

• PYTLARZ, JERZY;TABORSKA, JOANNA
  作者：PYTLARZ, JERZY、TABORSKA, JOANNA

  DOI：——

  日期：——
• PYTLARZ, J.;MIROSLAW, M.;TABORSKA, J.;ZARCZYNSKA, D.
  作者：PYTLARZ, J.、MIROSLAW, M.、TABORSKA, J.、ZARCZYNSKA, D.

  DOI：——

  日期：——
• ——
  作者：PYTLARZ J.、 TABORSKA J.

  DOI：——

  日期：——
• Novel synthetic isoquinolino[5,4-ab]phenazines: Inhibition toward topoisomerase I, antitumor and DNA photo-cleaving activities
  作者：Peng Yang、Qing Yang、Xuhong Qian、Jingnan Cui

  DOI：10.1016/j.bmc.2005.07.029

  日期：2005.11

  The novel DNA interactive isoquinolino[5,4-ab]phenazine derivatives were designed and synthesized. Their inhibitory abilities toward topoisomerase 1, antitumor activities and DNA photo-cleaving abilities were examined. The substituents at peri sites of two phenazine N atoms played very important roles for all these biological activities. At a concentration of 100 mu M, all these phenazine derivatives (but A2 and A6) exhibited an inhibitory activity toward topoisomerase I. A6 had efficient antitumor activities against both human lung cancer cell (A549) and murine leukemia cell (P388). A1, A5, and A6 exhibited antitumor activities selectively only against P388. A2 was the most efficient DNA photocleaver, which had converted supercoiled DNA from form I to form II at < 1 mu M. Under anaerobic conditions, the electron transfer mechanism mainly contributed to DNA photo-induced cleavage, while under aerobic conditions, superoxide anion was also involved in this process. (c) 2005 Elsevier Ltd. All rights reserved.