6-(Furan-2-ylmethyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione | 81721-81-5

• 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-(Furan-2-ylmethyl)-5H-indeno[1,2-c]isoquinoline-5,11(6H)-dione
• 英文别名: 6-(2-Furylmethyl)-5H-indeno(1,2-c)isoquinoline-5,11(6H)-dione；6-(furan-2-ylmethyl)indeno[1,2-c]isoquinoline-5,11-dione
• CAS: 81721-81-5
• 化学式: C₂₁H₁₃NO₃
• 分子量: 327.339
• InChiKey: ZPFUGHSCVQWWBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-Carboxyphenyl)-1,3-indandion 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 30.0h， 生成 6-(Furan-2-ylmethyl)-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

• WAWZONEK, S., ORG. PREP. AND PROCED. INT., 1982, 14, N 3, 163-168
  作者：WAWZONEK, S.

  DOI：——

  日期：——
• 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.