10-(环氧乙烷-2-基甲基)吖啶-9(10H)-酮 | 150389-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 10-(环氧乙烷-2-基甲基)吖啶-9(10H)-酮
• 英文名称: 10-oxiran-2-ylmethyl-10H-acridin-9-one
• 英文别名: 10-(Oxiran-2-ylmethyl)acridin-9(10H)-one；10-(oxiran-2-ylmethyl)acridin-9-one
• CAS: 150389-84-7
• 化学式: C₁₆H₁₃NO₂
• mdl: MFCD00726316
• 分子量: 251.285
• InChiKey: KRMZERAQRFRQKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-哌啶基哌啶 、 10-(环氧乙烷-2-基甲基)吖啶-9(10H)-酮 反应 0.08h， 以84%的产率得到10-(3-[1,4']bipiperidin-1'-yl-2-hydroxy-propyl)-10H-acridin-9-one
  参考文献：
  名称：

  Search for MDR modulators: Design, syntheses and evaluations of N-substituted acridones for interactions with p-glycoprotein and Mg2+

  摘要：

  By combining the structural features of acridone based anti-cancer drugs (like amsacrine) and MDR modulator propafenone, acridones with hydroxyl amine chain at N-10 have been designed and synthesized. These molecules exhibit appreciable interactions with p-gp and Mg2+ indicating their suitability to modulate p-gp mediated multi drug resistance. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.002
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 硫酸 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 19.5h， 生成 10-(环氧乙烷-2-基甲基)吖啶-9(10H)-酮
  参考文献：
  名称：

  A fluorescent probe for estimation of adenosine diphosphate and monitoring of glucose metabolism

  摘要：

  确定了一种在水介质中起作用的 ADP 选择性荧光探针，并对荧光变化与 ADP 浓度的函数关系进行了标准化。利用这种探针，可以监测线粒体中与 ATP/ADP 相互转化和丙酮酸氧化分解有关的所有糖酵解步骤，并对每个步骤中 ATP/ADP 的消耗/产生进行量化。此外，还测定了从猪身体不同部位提取的线粒体中的 ADP 含量。据推测，对该技术进行适当改良，可为监测生化途径以及快速估算线粒体和其他细胞器中的 ADP 提供诊断工具。

  DOI：

  10.1039/c3ob42505c

文献信息

• ATP selective acridone based fluorescent probes for monitoring of metabolic events
  作者：Jatinder Kaur、Palwinder Singh

  DOI：10.1039/c1cc10253b

  日期：——

  Acridones carrying an appropriate substituent at N-10 showed significant fluorescence changes on interacting with ATP in HEPES buffer at pH 7.2. The selectivity and sufficient binding of these probes with ATP could be useful for monitoring of metabolic processes.

  在 N-10 处含有适当取代基的吖啶酮在 pH 值为 7.2 的 HEPES 缓冲液中与 ATP 发生作用时，荧光会发生显著变化。这些探针与 ATP 的选择性和充分结合可用于监测代谢过程。
• Design, synthesis and evaluations of acridone derivatives using Candida albicans—Search for MDR modulators led to the identification of an anti-candidiasis agent
  作者：Palwinder Singh、Jatinder Kaur、Bhawna Yadav、Sneha Sudha Komath

  DOI：10.1016/j.bmc.2009.04.026

  日期：2009.6

  In order to search for MDR modulators, rationally designed acridone derivatives were investigated for their effect on influx or efflux of Rhodamine6G (R6G) in CAI4 cells. Results of these investigations indicate that in presence of compound 12, inhibition of growth of CAI4 cells and also an increased influx/efflux of R6G in CAI4 cells have been observed. This seems to be occurring due to the cell wall rupturing of Candida albicans. Compound 12 may be a suitable candidate for candidiasis therapy. (C) 2009 Elsevier Ltd. All rights reserved.
• Search for MDR modulators: Design, syntheses and evaluations of N-substituted acridones for interactions with p-glycoprotein and Mg2+
  作者：Palwinder Singh、Jatinder kaur、Prabhjit Kaur、Satwinderjeet Kaur

  DOI：10.1016/j.bmc.2009.02.002

  日期：2009.3

  By combining the structural features of acridone based anti-cancer drugs (like amsacrine) and MDR modulator propafenone, acridones with hydroxyl amine chain at N-10 have been designed and synthesized. These molecules exhibit appreciable interactions with p-gp and Mg2+ indicating their suitability to modulate p-gp mediated multi drug resistance. (C) 2009 Elsevier Ltd. All rights reserved.
• A fluorescent probe for estimation of adenosine diphosphate and monitoring of glucose metabolism
  作者：Arun Kumar、Parteek Prasher、Palwinder Singh

  DOI：10.1039/c3ob42505c

  日期：——

  An ADP selective fluorescent probe working in aqueous medium was identified and the change in fluorescence as a function of ADP concentration was standardized. Using this probe, all the steps of glycolysis coupled with ATP/ADP inter-conversion and oxidative breakdown of pyruvate in the mitochondria were monitored and the consumption/production of ATP/ADP at each step was quantified. The quantity of ADP present in the mitochondria, taken from different body parts of a pig, was also determined. It is hypothesized that an appropriate modification of the technique may provide a diagnostic tool for monitoring biochemical pathways as well as for quick estimation of ADP in the mitochondria and other cell organelles.

  确定了一种在水介质中起作用的 ADP 选择性荧光探针，并对荧光变化与 ADP 浓度的函数关系进行了标准化。利用这种探针，可以监测线粒体中与 ATP/ADP 相互转化和丙酮酸氧化分解有关的所有糖酵解步骤，并对每个步骤中 ATP/ADP 的消耗/产生进行量化。此外，还测定了从猪身体不同部位提取的线粒体中的 ADP 含量。据推测，对该技术进行适当改良，可为监测生化途径以及快速估算线粒体和其他细胞器中的 ADP 提供诊断工具。