3-nitro-[2-(2-isothiocyanatoethyl)]-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1314476-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-nitro-[2-(2-isothiocyanatoethyl)]-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-(2-Isothiocyanatoethyl)-5-nitrobenzo[de]isoquinoline-1,3-dione
• CAS: 1314476-46-4
• 化学式: C₁₅H₉N₃O₄S
• 分子量: 327.32
• InChiKey: QYHFKZSFABCINS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-硝基-1,8-萘二甲酸酐 在 potassium carbonate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 2.0h， 生成 3-nitro-[2-(2-isothiocyanatoethyl)]-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Development of novel naphthalimide derivatives and their evaluation as potential melanoma therapeutics

  摘要：

  Synthesis and anti-melanoma activity of various naphthalimide analogs, rationally modified by introducing isothiocyanate (ITC) and thiourea (TU) functionalities, found in well-known anti-cancer agents, is described. The structure activity relationship comparison of the novel agents in inhibiting cancer cell growth was evaluated in various melanoma cell lines. Both ITC and TU analogs effectively inhibited cell viability and induced apoptosis in various human melanoma cells. Nitro substitution and increase in alkyl chain length, in general, enhanced the apoptotic activity of ITC derivatives. All the new compounds were well tolerated when injected intraperitoneal (i.p.) in mice at effective doses at which both the ITC and TU derivatives inhibited melanoma tumor growth in mice following i.p. xenograft. The nitro substituted naphthalimide ITC derivative 3d was found to be the most effective in inducing apoptosis, and in inhibiting melanoma cell and tumor growth. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.058

文献信息

• Development of novel naphthalimide derivatives and their evaluation as potential melanoma therapeutics
  作者：Ugir Hossain Sk、A.S. Prakasha Gowda、Melissa A. Crampsie、Jong K. Yun、Thomas E. Spratt、Shantu Amin、Arun K. Sharma

  DOI：10.1016/j.ejmech.2011.04.058

  日期：2011.8

  Synthesis and anti-melanoma activity of various naphthalimide analogs, rationally modified by introducing isothiocyanate (ITC) and thiourea (TU) functionalities, found in well-known anti-cancer agents, is described. The structure activity relationship comparison of the novel agents in inhibiting cancer cell growth was evaluated in various melanoma cell lines. Both ITC and TU analogs effectively inhibited cell viability and induced apoptosis in various human melanoma cells. Nitro substitution and increase in alkyl chain length, in general, enhanced the apoptotic activity of ITC derivatives. All the new compounds were well tolerated when injected intraperitoneal (i.p.) in mice at effective doses at which both the ITC and TU derivatives inhibited melanoma tumor growth in mice following i.p. xenograft. The nitro substituted naphthalimide ITC derivative 3d was found to be the most effective in inducing apoptosis, and in inhibiting melanoma cell and tumor growth. (C) 2011 Elsevier Masson SAS. All rights reserved.