(R)-2-(1-hydroxybutan-2-yl)-1H-benzo[de]isoquinoline-1,3 (2H)-dione | 200057-54-1

• 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: (R)-2-(1-hydroxybutan-2-yl)-1H-benzo[de]isoquinoline-1,3 (2H)-dione
• 英文别名: (R)-2-(1-hydroxybutan-2-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione；2-[(2R)-1-hydroxybutan-2-yl]benzo[de]isoquinoline-1,3-dione
• CAS: 200057-54-1
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: AMQUOGIQAXFOJS-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(1-hydroxybutan-2-yl)-1H-benzo[de]isoquinoline-1,3 (2H)-dione 在 吡啶 、 盐酸羟胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 C₂₅H₁₈N₂O₇
  参考文献：
  名称：

  N-羟基邻苯二甲酰亚胺催化剂作为生物活性助氧化剂†

  摘要：

  的催化作用Ñ -hydroxyphthalimide（NHPI）在促进自由基氢原子转移（HAT）反应的，记录用于工业和合成感兴趣的过程，在此研究了在生物环境中的第一次。尽管NHPI本身未显示任何生物活性，但选定的NHPI衍生物（NHPIDs）却具有激活细胞内活性氧物种（ROS）形成的能力，从而导致谷胱甘肽（GSH）耗竭并增加了氧化应激（OS） ）。这些衍生物中的某些具有明显的生物活性，导致骨肉瘤MG-63的活力显着降低，这表明NHPIDs作为促氧化剂药物具有新的潜在作用。证明了N–OH基团在促进氧化应激中的关键作用。

  DOI：

  10.1039/c5ra26556h
• 作为产物：
  描述：

  1,8-萘二甲酸酐 、 2-氨基丁醇 以 乙醇 为溶剂， 反应 24.0h， 以71%的产率得到(R)-2-(1-hydroxybutan-2-yl)-1H-benzo[de]isoquinoline-1,3 (2H)-dione
  参考文献：
  名称：

  Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol – The crucial role of the configuration

  摘要：

  The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 mu M-14.03 mu M. Five of the most active compounds 11, 22, 23, 31 and 42(5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H(37)Rv showing no activity even at 20-32 fold higher concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.035

文献信息

• Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol – The crucial role of the configuration
  作者：Georgi M. Dobrikov、Violeta Valcheva、Margarita Stoilova-Disheva、Georgi Momekov、Pavleta Tzvetkova、Angel Chimov、Vladimir Dimitrov

  DOI：10.1016/j.ejmech.2011.11.035

  日期：2012.2

  The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 mu M-14.03 mu M. Five of the most active compounds 11, 22, 23, 31 and 42(5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H(37)Rv showing no activity even at 20-32 fold higher concentrations. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Sunlight Induced Oxidative Photoactivation of<i>N</i>-Hydroxyphthalimide Mediated by Naphthalene Imides
  作者：Lucio Melone、Paola Franchi、Marco Lucarini、Carlo Punta

  DOI：10.1002/adsc.201300611

  日期：2013.11.11

  AbstractWe report the aerobic photoactivation of N‐hydroxyphthlimide (NHPI) to the phthalimido‐N‐oxyl (PINO) radical mediated by naphthalene monoimides (NI) for promoting the selective oxidation of alkylaromatics and allylic compounds to the corresponding hydroperoxides. In the absence of either NI or NHPI no oxidation was observed, meaning that the two molecules operate in a synergistic way. Sunlight as well as artificial UV‐light irradiation was necessary in order to perform the process at low temperature (30–35 °C). EPR spectroscopy confirmed the role of NI and oxygen in promoting the formation of the superoxide radicals O2.− which, in turn, increased the concentration of PINO radicals during the UV light irradiation of NI/NHPI mixtures in MeCN. The investigation was extended to NI bearing different substituents on the naphthalene moiety. Finally, the synthesis and application of a unique photocatalyst including the NI and NHPI moieties linked by a suitable spacer was also considered. In this case the photocatalyst showed a substrate‐dependent behaviour with some peculiarities in comparison to the system where NI and NHPI are independent units in the same reacting system. This photocatalytic system paves the way to a non‐thermal, metal‐free approach for CH bond activation towards aerobic oxidation under very mild conditions.magnified image
• N-Hydroxyphthalimide catalysts as bioactive pro-oxidants
  作者：L. Melone、P. Tarsini、G. Candiani、C. Punta

  DOI：10.1039/c5ra26556h

  日期：——

  The catalytic role of N-hydroxyphthalimide (NHPI) in promoting free-radical hydrogen atom transfer (HAT) reactions, well-documented for processes of industrial and synthetic interest, is here investigated for the first time in a biological environment. While NHPI by itself did not show any bioactivity, selected NHPI-derivatives (NHPIDs) revealed the ability to activate the intracellular formation of

  的催化作用Ñ -hydroxyphthalimide（NHPI）在促进自由基氢原子转移（HAT）反应的，记录用于工业和合成感兴趣的过程，在此研究了在生物环境中的第一次。尽管NHPI本身未显示任何生物活性，但选定的NHPI衍生物（NHPIDs）却具有激活细胞内活性氧物种（ROS）形成的能力，从而导致谷胱甘肽（GSH）耗竭并增加了氧化应激（OS） ）。这些衍生物中的某些具有明显的生物活性，导致骨肉瘤MG-63的活力显着降低，这表明NHPIDs作为促氧化剂药物具有新的潜在作用。证明了N–OH基团在促进氧化应激中的关键作用。