5-chloroisoindigo | 701257-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-chloroisoindigo
• 英文别名: 5-chloro-1H,1'H-[3,3']biindolylidene-2,2'-dione；5-Chlor-1H,1'H-[3,3']biindolyliden-2,2'-dion；5-chloro-3-(2-oxo-1H-indol-3-ylidene)-1H-indol-2-one
• CAS: 701257-99-0
• 化学式: C₁₆H₉ClN₂O₂
• 分子量: 296.713
• InChiKey: ZLNLMKPDRVWLRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  21.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-chloroisoindigo 在 4-二甲氨基吡啶 、 platinum(IV) oxide 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 di-tert-butyl 5-chloro-2,2'-dioxo-[3,3'-biindoline]-1,1'-dicarboxylate
  参考文献：
  名称：

  有机阳离子催化双吲哚的不对称均/杂-二烷基化：邻位全碳四元立体中心的构建和(-)-Chimonanthidine的全合成

  摘要：

  设计并证明了一种新型手性螺环酰胺 (SPA) 衍生的三唑鎓有机催化剂可实现各种双氧吲哚的不对称同二烷基化和杂二烷基化，从而实现邻位全碳四元立体中心的对映选择性构建。这些反应具有出色的对映选择性和非对映选择性（高达 99% ee 和 >20:1 dr）以及良好的产率（两步高达 89%）。作为该方法的应用，已经实现了 (-)-chimonanthidine 的第一个不对称全合成。

  DOI：

  10.1021/jacs.8b05386
• 作为产物：
  描述：

  2-吲哚酮 、 5-氯靛红 在 Sulfonic-acid-functionalized nanoporous silica 作用下， 反应 0.2h， 以80%的产率得到5-chloroisoindigo
  参考文献：
  名称：

  Efficient green synthesis of isoindigo derivatives using sulfonic-acid-functionalized nanoporous silica (SBA-Pr-SO3H) catalyst and study of their antimicrobial properties

  摘要：

  已开发出一种高效的绿色缩合反应，使用孔径为6纳米的SBA-Pr-SO3H作为异质纳米孔酸催化剂，在无溶剂条件下合成trans-异苯骈二氮杂环衍生物。异苯骈二氮杂环衍生物在染料、药物、有机太阳能电池和半导体存储等多个工业领域有广泛应用。这些化合物的抗菌活性也进行了测试。

  DOI：

  10.1007/s11164-012-0909-y

文献信息

• Functionalized 3-benzylidene-indolin-2-ones: Inducers of NAD(P)H-quinone oxidoreductase 1 (NQO1) with antiproliferative activity
  作者：Wei Zhang、Mei-Lin Go

  DOI：10.1016/j.bmc.2008.12.052

  日期：2009.3

  Functionalized benzylidene-indolin-2-ones are widely associated with antiproliferative activity. The scaffold is not normally associated with chemoprevention in spite of the presence of a nitrogen-linked Michael acceptor moiety that may predispose members to induction of NQO1, a widely used biomarker of chemopreventive potential. To investigate this possibility, we have synthesized and evaluated a series of functionalized 3-benzylidene-indolin-2-ones for induction of NQO1 in murine Hepa1c1c7 cells as well as antiproliferative activity against two human cancer cell lines (MCF-7, HCT116). The benzylideneindolinones were found to be good inducers of NQO1 activity, with 85% of test compounds able to increase basal NQO1 activity by more than twofold at concentrations of <= 10 mu M. By contrast, fewer compounds (11%) tested at the same concentration were able to reduce cell viability by more than 50%. Structure activity relationships showed that the nitrogen linked Michael acceptor moiety was an essential requirement for both activities. This common feature notwithstanding, substitution of the 3-benzylidene-indolin-2-one core structure affected NQO1 induction and antiproliferative activities in dissimilar ways, underscoring different structural requirements for these two activities. Nonetheless, promising compounds ( 10, 42, 45-48) were identified that combine selective induction of NQO1 with potent antiproliferative activity. A potential advantage of such agents would be the ability to provide added protection to normal cells by the up-regulation of NQO1 and other phase II enzymes while simultaneously targeting neoplastic cells. (C) 2008 Elsevier Ltd. All rights reserved.
• Wahl; Fericean, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1928, vol. 186, p. 379
  作者：Wahl、Fericean

  DOI：——

  日期：——
• Viral Modulators and Processes Thereof
  申请人：Kashanchi Fatah

  公开号：US20120190009A1

  公开（公告）日：2012-07-26

  A viral modulator and process thereof. A method may include contacting one or more viral modulators to one or more biological systems. A biological system may be configured to be infected by one or more virus. A virus may include an HIV virus, a VEEV virus and/or the like. A viral modulator may include a viral inhibitor and/or a viral activator.
• VIRAL MODULATORS AND PROCESSES THEREOF
  申请人：Kashanchi Fatah

  公开号：US20120190723A1

  公开（公告）日：2012-07-26

  A viral modulator and process thereof. A method may include contacting one or more viral modulators to one or more biological systems. A biological system may be configured to be infected by one or more virus. A virus may include an HIV virus, a VEEV virus and/or the like. A viral modulator may include a viral inhibitor and/or a viral activator.