4-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)benzenesulfonamide | 1353887-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)benzenesulfonamide
• CAS: 1353887-59-8
• 化学式: C₁₈H₁₁N₃O₆S
• 分子量: 397.368
• InChiKey: XYOHKAMFUSAQFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140.68
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)benzenesulfonamide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 N-((4-(1,3-dioxo-6-((thiophen-2-ylmethyl)amino)-1H-benzo[de]isoquinolin-2(3H)-yl)phenyl)sulfonyl)-4-(4-(3,3-diphenylallyl)piperazin-1-yl)benzamide
  参考文献：
  名称：

  Novel Naphthalimide-Benzoic Acid Conjugates as Potential Apoptosis-Inducing Agents: Design, Synthesis, and Biological Activity

  摘要：

  A series of novel naphthalimide derivatives with 4‐[4‐(3,3‐diphenylallyl)piperazin‐1‐yl]benzoic acid as side chain were designed and synthesized. Their antitumor activities were evaluated against a variety of cancer cell lines in vitro. Preliminary results showed that most of the derivatives had cytotoxic activity comparable with that of amonafide, with IC50 values of 10−6–10−5 m. Interestingly, compound 12e had the unique antitumor activity against MCF‐7 among the cancer cell lines tested. More importantly, flow cytometric analysis indicated that compared with amonafide, the target compounds could effectively induce G2/M arrest and progress to apoptosis in HL‐60 cells after double staining with annexin V–FITC and propidium iodide. The present work provided a novel class of naphthalimide‐based derivatives with potential apoptosis‐inducing and improved antitumor activity for further optimization.

  DOI：

  10.1111/j.1747-0285.2011.01232.x
• 作为产物：
  描述：

  4-硝基-1,8-萘醛酸酐 、 磺胺 在 溶剂黄146 作用下， 反应 5.0h， 以75%的产率得到4-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)benzenesulfonamide
  参考文献：
  名称：

  Novel Naphthalimide-Benzoic Acid Conjugates as Potential Apoptosis-Inducing Agents: Design, Synthesis, and Biological Activity

  摘要：

  A series of novel naphthalimide derivatives with 4‐[4‐(3,3‐diphenylallyl)piperazin‐1‐yl]benzoic acid as side chain were designed and synthesized. Their antitumor activities were evaluated against a variety of cancer cell lines in vitro. Preliminary results showed that most of the derivatives had cytotoxic activity comparable with that of amonafide, with IC50 values of 10−6–10−5 m. Interestingly, compound 12e had the unique antitumor activity against MCF‐7 among the cancer cell lines tested. More importantly, flow cytometric analysis indicated that compared with amonafide, the target compounds could effectively induce G2/M arrest and progress to apoptosis in HL‐60 cells after double staining with annexin V–FITC and propidium iodide. The present work provided a novel class of naphthalimide‐based derivatives with potential apoptosis‐inducing and improved antitumor activity for further optimization.

  DOI：

  10.1111/j.1747-0285.2011.01232.x