7'-iodo-1'-(naphthalen-2-ylmethyl)spiro[[1,3]-dioxolane-2,3'-indolin]-2'-one | 1393654-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7'-iodo-1'-(naphthalen-2-ylmethyl)spiro[[1,3]-dioxolane-2,3'-indolin]-2'-one
• CAS: 1393654-32-4
• 化学式: C₂₁H₁₆INO₃
• 分子量: 457.267
• InChiKey: PTILTVDDHOJBCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  7'-iodo-1'-(naphthalen-2-ylmethyl)spiro[[1,3]-dioxolane-2,3'-indolin]-2'-one 在 四丁基溴化铵 、 sodium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以67%的产率得到spiro[benzo[l]pyrrolo[3,2,1-de]phenanthridine-4,2'-[1,3]dioxolan]-5(7H)-one
  参考文献：
  名称：

  Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2-diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives

  摘要：

  To further expand the structure cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 mu M) after 24 h. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.049
• 作为产物：
  描述：

  2-iodohydroxyiminoacetanilide 在 硫酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 66.83h， 生成 7'-iodo-1'-(naphthalen-2-ylmethyl)spiro[[1,3]-dioxolane-2,3'-indolin]-2'-one
  参考文献：
  名称：

  Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2-diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives

  摘要：

  To further expand the structure cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 mu M) after 24 h. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.049

文献信息

• Synthesis and anti-leukaemic activity of pyrrolo[3,2,1-hi]indole-1,2-diones, pyrrolo[3,2,1-ij]quinoline-1,2-diones and other polycyclic isatin derivatives
  作者：Lidia Matesic、Julie M. Locke、Kara L. Vine、Marie Ranson、John B. Bremner、Danielle Skropeta

  DOI：10.1016/j.tet.2012.06.049

  日期：2012.8

  To further expand the structure cytotoxic activity relationships of isatin derivatives and to reduce flexibility in substituent groups at nitrogen, 20 analogues incorporating a ring system between the N1 and C7 atoms of isatin were prepared using a variety of synthetic strategies. This yielded pyrroloindole-, pyrroloquinoline-, pyrroloacridine-, pyrrolophenanthridine- and benzopyrrolophenanthridine-based systems with embedded isatin moieties, the latter possessing a novel carbon skeleton. These compounds were subsequently assessed for their in vitro cytotoxicity against human U937 lymphoma cells, with the brominated pyrroloacridine dione 27 showing the most promising activity (IC50 3.01 mu M) after 24 h. (C) 2012 Elsevier Ltd. All rights reserved.