6-(3-azido-2-hydroxypropyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-(3-azido-2-hydroxypropyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione
• 英文别名: 6-(3-Azido-2-hydroxypropyl)indeno[1,2-c]isoquinoline-5,11-dione；6-(3-azido-2-hydroxypropyl)indeno[1,2-c]isoquinoline-5,11-dione
• 化学式: C₁₉H₁₄N₄O₃
• 分子量: 346.345
• InChiKey: QBWIKULRJCPSRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(3-azido-2-hydroxypropyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione 在 copper(l) iodide 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (1-(2-acetoxy-3-(5,11-dioxo-5,11-dihydro-6H-indeno[1,2-c]isoquinolin-6-yl)propyl)-1H-1,2,3-triazol-4-yl)methyl acetate
  参考文献：
  名称：

  新型茚并异喹啉取代的三唑杂化物的合成及细胞毒性评价

  摘要：

  各种取代的三唑-茚并异喹啉杂化物的合成是基于在炔丙基取代的衍生物与含叠氮化物的茚并异喹啉之间进行CuI催化的1,3-环加成反应而进行的。此外，多种N-（烷基）炔丙基腺苷异喹啉被用作通过3'-叠氮基-3'-脱氧胸苷（Click）化学介导的偶联而缀合的三唑-茚基异喹啉-AZT的底物。因此，成功制备了23种新的茚并异喹啉取代的三唑杂合体，并将其作为细胞毒性剂进行了评估，揭示了KB和HepG2癌细胞系中四种三唑连接基-茚异喹啉-AZT杂合体的有趣抗癌活性。

  DOI：

  10.1016/j.bmcl.2016.05.092
• 作为产物：
  描述：

  2-(2-Carboxyphenyl)-1,3-indandion 在 sodium azide 、 溴 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 6-(3-azido-2-hydroxypropyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione
  参考文献：
  名称：

  Synthesis and cytotoxic evaluation of novel indenoisoquinoline-propan-2-ol hybrids

  摘要：

  The synthesis of N-substituted indenoisoquinolines was performed by applying a two-step condensation between 2-carboxybenzaldehyde and phthalide, followed by treatment with various primary amines. N-allylindenoisoquinoline was subsequently selected as a substrate for hydroxybromination, providing 6-(3-bromo-2-hydroxy)indenoisoquinoline as a key intermediate for derivatization in the lactam side chain. In this way, a series of 6-(2-hydroxypropyl)indenoisoquinolines bearing various functional groups at the 3'-position were prepared, which can be considered as novel indenoisoquinoline-propan-2-ol hybrid molecules. Subsequent cytotoxic evaluation of 28 indenoisoquinolines against two human cancer cell lines (Hep-G2 and KB) demonstrated a moderate to high antiproliferative activity displayed by 11 indenoisoquinolines thus synthesized. In particular, the introduction of the 2-hydroxypropyl side chain was shown to be beneficial for the overall cytotoxic activity, pointing to the potential relevance of these novel indenoisoquinoline-propan-2-ol hybrids. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.12.045

文献信息

• Synthesis and cytotoxic evaluation of novel indenoisoquinoline-propan-2-ol hybrids
  作者：Tham Pham Thi、Lena Decuyper、Tan Luc Quang、Chinh Pham The、Tuyet Anh Dang Thi、Ha Thanh Nguyen、Thuy Giang Le Nhat、Tra Nguyen Thanh、Phuong Hoang Thi、Matthias D’hooghe、Tuyen Van Nguyen

  DOI：10.1016/j.tetlet.2015.12.045

  日期：2016.1

  The synthesis of N-substituted indenoisoquinolines was performed by applying a two-step condensation between 2-carboxybenzaldehyde and phthalide, followed by treatment with various primary amines. N-allylindenoisoquinoline was subsequently selected as a substrate for hydroxybromination, providing 6-(3-bromo-2-hydroxy)indenoisoquinoline as a key intermediate for derivatization in the lactam side chain. In this way, a series of 6-(2-hydroxypropyl)indenoisoquinolines bearing various functional groups at the 3'-position were prepared, which can be considered as novel indenoisoquinoline-propan-2-ol hybrid molecules. Subsequent cytotoxic evaluation of 28 indenoisoquinolines against two human cancer cell lines (Hep-G2 and KB) demonstrated a moderate to high antiproliferative activity displayed by 11 indenoisoquinolines thus synthesized. In particular, the introduction of the 2-hydroxypropyl side chain was shown to be beneficial for the overall cytotoxic activity, pointing to the potential relevance of these novel indenoisoquinoline-propan-2-ol hybrids. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and cytotoxic evaluation of novel indenoisoquinoline-substituted triazole hybrids
  作者：Tham Pham Thi、Thuy Giang Le Nhat、Thuong Ngo Hanh、Tan Luc Quang、Chinh Pham The、Tuyet Anh Dang Thi、Ha Thanh Nguyen、Thu Ha Nguyen、Phuong Hoang Thi、Tuyen Van Nguyen

  DOI：10.1016/j.bmcl.2016.05.092

  日期：2016.8

  The synthesis of various substituted triazole–indenoisoquinoline hybrids was performed based on a CuI-catalyzed 1,3-cycloaddition between propargyl-substituted derivatives and the azide-containing indenoisoquinoline. Besides, a variety of N-(alkyl)propargylindenoisoquinolines was used as substrates for the construction of triazole–indenoisoquinoline–AZT conjugated via a click chemistry-mediated coupling

  各种取代的三唑-茚并异喹啉杂化物的合成是基于在炔丙基取代的衍生物与含叠氮化物的茚并异喹啉之间进行CuI催化的1,3-环加成反应而进行的。此外，多种N-（烷基）炔丙基腺苷异喹啉被用作通过3'-叠氮基-3'-脱氧胸苷（Click）化学介导的偶联而缀合的三唑-茚基异喹啉-AZT的底物。因此，成功制备了23种新的茚并异喹啉取代的三唑杂合体，并将其作为细胞毒性剂进行了评估，揭示了KB和HepG2癌细胞系中四种三唑连接基-茚异喹啉-AZT杂合体的有趣抗癌活性。