2-(6-(2-(dimethylamino)ethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-4-methylpentanoic acid | 1134196-02-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(6-(2-(dimethylamino)ethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-4-methylpentanoic acid
• CAS: 1134196-02-3
• 化学式: C₂₂H₂₇N₃O₄
• 分子量: 397.474
• InChiKey: OKLKDUYSGQZJHS-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  89.95
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  联大茴香胺 、 2-(6-(2-(dimethylamino)ethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-4-methylpentanoic acid 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 氯仿 为溶剂， 反应 48.0h， 以55%的产率得到N-(4'-amino-3,3'-dimethoxybiphenyl-4-yl)-2-(6-(2-(dimethylamino)ethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-4-methylpentanamide
  参考文献：
  名称：

  Novel naphthalimide–amino acid conjugates with flexible leucine moiety as side chain: Design, synthesis and potential antitumor activity

  摘要：

  A series of novel naphthalimide derivatives with flexible leucine side chains were designed and synthesized. Their antitumor activities were evaluated against HeLa, A549, P388, HL-60, MCF-7, HCT-8 and A375 cancer cell lines in vitro. The preliminary results showed that most of the derivatives had moderate antitumor activities with the IC50 values of 10 (6) - 10 (5) M. More importantly, compounds 8a-c exhibited exclusive antitumor activities against MCF-7 cell line. The interaction between compound 8b and BSA was also investigated. DNA binding experiments showed that these derivatives behaved as DNA intercalating agents. This work provided a novel class of naphthalimide-based lead compounds with exclusive antitumor activities against MCF-7 cell line for further optimization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.080
• 作为产物：
  描述：

  methyl 2-(6-(2-(dimethylamino)ethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-4-methylpentanoate 在 lithium hydroxide monohydrate 、 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以96%的产率得到2-(6-(2-(dimethylamino)ethylamino)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-4-methylpentanoic acid
  参考文献：
  名称：

  Novel naphthalimide–amino acid conjugates with flexible leucine moiety as side chain: Design, synthesis and potential antitumor activity

  摘要：

  A series of novel naphthalimide derivatives with flexible leucine side chains were designed and synthesized. Their antitumor activities were evaluated against HeLa, A549, P388, HL-60, MCF-7, HCT-8 and A375 cancer cell lines in vitro. The preliminary results showed that most of the derivatives had moderate antitumor activities with the IC50 values of 10 (6) - 10 (5) M. More importantly, compounds 8a-c exhibited exclusive antitumor activities against MCF-7 cell line. The interaction between compound 8b and BSA was also investigated. DNA binding experiments showed that these derivatives behaved as DNA intercalating agents. This work provided a novel class of naphthalimide-based lead compounds with exclusive antitumor activities against MCF-7 cell line for further optimization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.080