6-(4-chlorophenyl)-7H-[1,3]dioxolo [4,5-f]indol-7-one-5-oxide | 773075-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 6-(4-chlorophenyl)-7H-[1,3]dioxolo [4,5-f]indol-7-one-5-oxide
• 英文别名: 6-(4-Chlorophenyl)-5-oxido-[1,3]dioxolo[4,5-f]indol-5-ium-7-one
• CAS: 773075-14-2
• 化学式: C₁₅H₈ClNO₄
• 分子量: 301.686
• InChiKey: NUWYERFBSACXKE-UHFFFAOYSA-N

物化性质

• 熔点：
  210-211 °C
• 沸点：
  535.7±60.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-methoxystyrene)boronic acid 、 6-(4-chlorophenyl)-7H-[1,3]dioxolo [4,5-f]indol-7-one-5-oxide 反应 24.0h， 以55%的产率得到(E)-6-(4-chlorophenyl)-5-hydroxy-6-(4-methoxystyryl)-5,6-dihydro-7H-[1,3]dioxolo[4,5-f]indol-7-one
  参考文献：
  名称：

  Isatogens 与硼酸的区域选择性交叉偶联构建 2,2-二取代 Indolin-3-one 衍生物

  摘要：

  在本文中，我们通过硼“ate”配合物的 1,4-金属盐转移，提出了一种无过渡金属的交叉偶联反应，即靛蓝原与硼酸。这种偶联反应提供了一种可行的方法来提供有价值的 2,2-二取代 indolin-3-one 衍生物，具有优异的区域选择性，具有操作简单、良好的官能团耐受性和广泛的底物范围。

  DOI：

  10.1021/acs.orglett.1c02808
• 作为产物：
  描述：

  5-(4-Chloro-phenylethynyl)-6-nitro-benzo[1,3]dioxole 在 双(乙腈)氯化钯(II) 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以36%的产率得到6-(4-chlorophenyl)-7H-[1,3]dioxolo [4,5-f]indol-7-one-5-oxide
  参考文献：
  名称：

  Isatogens 与硼酸的区域选择性交叉偶联构建 2,2-二取代 Indolin-3-one 衍生物

  摘要：

  在本文中，我们通过硼“ate”配合物的 1,4-金属盐转移，提出了一种无过渡金属的交叉偶联反应，即靛蓝原与硼酸。这种偶联反应提供了一种可行的方法来提供有价值的 2,2-二取代 indolin-3-one 衍生物，具有优异的区域选择性，具有操作简单、良好的官能团耐受性和广泛的底物范围。

  DOI：

  10.1021/acs.orglett.1c02808

文献信息

• Synthesis and Antiplasmodial Activity of New Indolone <i>N</i>-Oxide Derivatives
  作者：Françoise Nepveu、Sothea Kim、Jeremie Boyer、Olivier Chatriant、Hany Ibrahim、Karine Reybier、Marie-Carmen Monje、Severine Chevalley、Pierre Perio、Barbora H. Lajoie、Jalloul Bouajila、Eric Deharo、Michel Sauvain、Rachida Tahar、Leonardo Basco、Antonella Pantaleo、Francesco Turini、Paolo Arese、Alexis Valentin、Eloise Thompson、Livia Vivas、Serge Petit、Jean-Pierre Nallet

  DOI：10.1021/jm901300d

  日期：2010.1.28

  A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), its well as for cytotoxic concentration (CC50) on MCF7 and KB human tumor Cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (< 3 nM on FcB1 and = 1.7 nM on 3D7) with a very satisfactory selectivity index (CC50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day.
• Pro-oxidant properties of indolone-N-oxides in relation to their antimalarial properties
  作者：Nguyen Thi Hoang Yen、Hany Ibrahim、Karine Reybier、Pierre Perio、Florence Souard、Ennaji Najahi、Paul-Louis Fabre、Francoise Nepveu

  DOI：10.1016/j.jinorgbio.2013.04.012

  日期：2013.9

  Indolone-N-oxides (INODs) are bioreducible and possess remarkable anti-malarial activities in the low nanomolar range in vitro against different Plasmodium falciparum (P. falciparum) strains and in vivo. INODs have an original mechanism of action: they damage the host cell membrane without affecting non-parasitized erythrocytes. These molecules produce a redox signal which activates SYK tyrosine kinases and induces a hyperphosphorylation of AE1 (band 3, erythrocyte membrane protein). The present work aimed to understand the early stages of the biochemical interactions of these compounds with some erythrocyte components from which the redox signal could originate. The interactions were studied in a biomimetic model and compared with those of chloroquine and artemisinin. The results showed that INODs i) do not enter the coordination sphere of the metal in the heme iron complex as does chloroquine; ii) do not generate iron-dependent radicals as does artemisinin; iii) generate stable free radical adducts after reduction at one electron; iv) cannot trap free radicals after reduction. These results confirm that the bioactivity of INODs does not lie in their spin-trapping properties but rather in their pro-oxidant character. This property may be the initiator of the redox signal which activates SYK tyrosine kinases. (C) 2013 Elsevier Inc. All rights reserved.
• Regioselective Cross-Coupling of Isatogens with Boronic Acids to Construct 2,2-Disubstituted Indolin-3-one Derivatives
  作者：Hetao Xu、Mingxing Ye、Kai Yang、Qiuling Song

  DOI：10.1021/acs.orglett.1c02808

  日期：2021.10.15

  Herein we present a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron “ate” complex. This coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one derivatives with excellent regioselectivity, which exhibit operational simplicity, good functional group tolerance, and a broad substrate scope.

  在本文中，我们通过硼“ate”配合物的 1,4-金属盐转移，提出了一种无过渡金属的交叉偶联反应，即靛蓝原与硼酸。这种偶联反应提供了一种可行的方法来提供有价值的 2,2-二取代 indolin-3-one 衍生物，具有优异的区域选择性，具有操作简单、良好的官能团耐受性和广泛的底物范围。