2-nitro-6H-isoindolo[2,1-α]indol-6-one | 874751-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-nitro-6H-isoindolo[2,1-α]indol-6-one
• 英文别名: 2-nitro-6H-isoindolo[2,1-a]indol-6-one；2-nitroisoindolo[2,1-a]indol-6-one；2-Nitroisoindolo[2,3-a]indol-6-one
• CAS: 874751-99-2
• 化学式: C₁₅H₈N₂O₃
• 分子量: 264.24
• InChiKey: IBEHSQKDJGACCD-UHFFFAOYSA-N

物化性质

• 熔点：
  268.8 °C (decomp)
• 沸点：
  413.6±27.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-nitro-6H-isoindolo[2,1-α]indol-6-one 在 potassium tert-butylate 作用下， 以 水 、 叔丁醇 为溶剂， 生成 2-(5-硝基-1H-吲哚-2-基)苯甲酸
  参考文献：
  名称：

  Structure–activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus

  摘要：

  The synthesis of 22 2-aryl-1H-indoles, including 12 new compounds, has been achieved via Pd- or Rh-mediated methodologies, or selective electrophilic substitution. All three methods were based on elaborations from simple indole precursors. SAR studies on these indoles and 2-phenyl-1H-indole in Staphylococcus aureus as NorA efflux pump inhibitors indicated 5-nitro-2-(3-methoxycarbonyl)phenyl-1H-indole was a slightly more potent inhibitor than the lead INF55. A promising new antibacterial lead compound against S. aureus (2-phenyl-1H-indol-5-yl)-methanol, was also found. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.093
• 作为产物：
  描述：

  4-硝基-2-甲苯胺 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 56.0h， 生成 2-nitro-6H-isoindolo[2,1-α]indol-6-one
  参考文献：
  名称：

  Synthesis and biological activity of 6H-isoindolo[2,1-a]indol-6-ones, analogues of batracylin, and related compounds

  摘要：

  Closely related to batracylin, 6H-isoindolo[2,1-a]indol-6-ones including 2-nitro- 13a, 2-amino- 14, and 2-diethylaminopropionamide derivative 16 as well as D-ring substituted 13b, 13c or A-ring substituted 13d and 20 analogues, were synthesised and evaluated against L1210 leukaemia. Subsequent treatment of 13b and 13c with NN-diethylethylenediarnine at 180 degrees C, led to compounds 17a and 17b arising from an unexpected opening of the pyrrolidinone ring and amidification of the keto group. Under the same conditions, the dichloro derivative 13d led to the monoalkyl compound 20 which was the most cytotoxic of the series. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.008

文献信息

• Rhodium-Catalyzed NH-Indole-Directed C–H Carbonylation with Carbon Monoxide: Synthesis of 6<i>H</i>-Isoindolo[2,1-<i>a</i>]indol-6-ones
  作者：Qiufeng Huang、Qingshuai Han、Shurong Fu、Zizhu Yao、Lv Su、Xiaofeng Zhang、Shen Lin、Shengchang Xiang

  DOI：10.1021/acs.joc.6b01200

  日期：2016.12.16

  An efficient synthesis of 6H-isoindolo[2,1-a]indol-6-ones through rhodium-catalyzed NH-indole-directed C–H carbonylation of 2-arylindoles with carbon monoxide has been developed. Preliminary mechanistic studies revealed that this reaction proceeds via N–H bond cleavage and subsequent C–H bond cleavage. Reaction monitoring via ESI-MS was used to support the formation of five-membered rhodacycle species

  通过铑催化一氧化碳2-芳基吲哚的NH-吲哚定向的CH羰基化羰基反应，已开发出6 H-异吲哚并[2,1 - a ]吲哚-6-酮的有效合成方法。初步的机理研究表明，该反应通过NH键断裂和随后的CH键断裂进行。通过ESI-MS进行的反应监测用于支持催化循环中五元罗丹环物种的形成。
• 一种6H-异吲哚并[2,1-α]吲哚-6-酮衍生物的 合成方法
  申请人：福建师范大学

  公开号：CN104892614B

  公开（公告）日：2017-11-07

  本发明公开了一种6H‑异吲哚并[2,1‑α]吲哚‑6‑酮衍生物的合成方法，包括如下步骤：在高压釜中将2‑(2‑碘苯基)‑吲哚、催化剂、配体、碱放入有机溶剂中，体系中充入一定压力的CO气体进行羰基化反应，反应完成后通过柱层析分离得到6H‑异吲哚并[2,1‑α]吲哚‑6‑酮衍生物。本发明采用一氧化碳作为碳源一步合成6H‑异吲哚并[2,1‑α]吲哚‑6‑酮衍生物，催化体系简单，操作简便。
• Synthesis of functionalised 2-aryl-5-nitro-1H-indoles and their activity as bacterial NorA efflux pump inhibitors
  作者：Siritron Samosorn、John B. Bremner、Anthony Ball、Kim Lewis

  DOI：10.1016/j.bmc.2005.09.019

  日期：2006.2

  In order to develop structure-activity relationships and to provide access to antibacterial agents for dual action studies, a variety of aryl group-substituted 2-aryl-5-nitro-1H-indoles were synthesized and the activity of the compounds assessed as inhibitors of the NorA multidrug resistance pump in the bacterium Staphylococcus aureus. The NorA protein from the major facilitator superfamily of efflux pumps confers resistance to a variety of structurally dissimilar antimicrobials such as norfloxacin, ethidium bromide, berberine and acrillavin. The compound [4-benzyloxy-2-(5-nitro-1H-2-yl)-phenyl]-methanol was the most potent pump inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.
• Structure–activity relationships of 2-aryl-1H-indole inhibitors of the NorA efflux pump in Staphylococcus aureus
  作者：Joseph I. Ambrus、Michael J. Kelso、John B. Bremner、Anthony R. Ball、Gabriele Casadei、Kim Lewis

  DOI：10.1016/j.bmcl.2008.06.093

  日期：2008.8

  The synthesis of 22 2-aryl-1H-indoles, including 12 new compounds, has been achieved via Pd- or Rh-mediated methodologies, or selective electrophilic substitution. All three methods were based on elaborations from simple indole precursors. SAR studies on these indoles and 2-phenyl-1H-indole in Staphylococcus aureus as NorA efflux pump inhibitors indicated 5-nitro-2-(3-methoxycarbonyl)phenyl-1H-indole was a slightly more potent inhibitor than the lead INF55. A promising new antibacterial lead compound against S. aureus (2-phenyl-1H-indol-5-yl)-methanol, was also found. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and biological activity of 6H-isoindolo[2,1-a]indol-6-ones, analogues of batracylin, and related compounds
  作者：Jean Guillaumel、Stéphane Léonce、Alain Pierré、Pierre Renard、Bruno Pfeiffer、Paola B. Arimondo、Claude Monneret

  DOI：10.1016/j.ejmech.2005.10.008

  日期：2006.3

  Closely related to batracylin, 6H-isoindolo[2,1-a]indol-6-ones including 2-nitro- 13a, 2-amino- 14, and 2-diethylaminopropionamide derivative 16 as well as D-ring substituted 13b, 13c or A-ring substituted 13d and 20 analogues, were synthesised and evaluated against L1210 leukaemia. Subsequent treatment of 13b and 13c with NN-diethylethylenediarnine at 180 degrees C, led to compounds 17a and 17b arising from an unexpected opening of the pyrrolidinone ring and amidification of the keto group. Under the same conditions, the dichloro derivative 13d led to the monoalkyl compound 20 which was the most cytotoxic of the series. (c) 2006 Elsevier SAS. All rights reserved.