4,5-dimethoxy-2-nitroacetophenone hydrazone | 123642-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-dimethoxy-2-nitroacetophenone hydrazone
• 英文别名: [1-(4,5-Dimethoxy-2-nitrophenyl)ethylidene]hydrazine；1-(4,5-dimethoxy-2-nitrophenyl)ethylidenehydrazine
• CAS: 123642-61-5
• 化学式: C₁₀H₁₃N₃O₄
• 分子量: 239.231
• InChiKey: FBDMXPWHQWYTQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxy-2-nitroacetophenone hydrazone 在 manganese(IV) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 1-(4,5-dimethoxy-2-nitrophenyl)diazoethane
  参考文献：
  名称：

  Caged agonist of P2Y1 and P2Y12 receptors for light-directed facilitation of platelet aggregation

  摘要：

  We have prepared a caged form (MRS2703) of a potent dual agonist of the P2Y(1) and P2Y(12) nucleotide receptors, 2-MeSADP, by blocking the p-phosphate group with a 1-(3,4-dimethyloxyphenyl)eth-1-yl phosphoester. Although MRS2703 is itself inactive at human P2Y(1) and P2Y(12) receptors expressed heterologously in 1321N1 astrocytoma cells or in washed human platelets, this derivative readily regenerates the parent agonist upon mild irradiation with long-wave UV light (360 nm). The functional effect of the regenerated agonist was demonstrated by a rise in intracellular calcium mediated by either P2Y(1) or P2Y(12) receptors in transfected cells. Washed human platelets exposed to a solution of MRS2703 were induced to aggregate upon UV irradiation. At 1.0 mu M MRS2703, full aggregation was achieved within 1 min of irradiation. Thus, this caged nucleotide promises to be a useful probe for potent P2Y receptor activation with light-directed spatial and temporal control. Published by Elsevier Inc.

  DOI：

  10.1016/j.bcp.2007.10.037
• 作为产物：
  描述：

  1-(4,5-二甲氧基-2-硝基苯基)乙酮 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以53%的产率得到4,5-dimethoxy-2-nitroacetophenone hydrazone
  参考文献：
  名称：

  Chemo-enzymatic synthesis and biological evaluation of photolabile nicotinic acid adenine dinuclotide phosphate (NAADP⁺)

  摘要：

  成功实现了一种新的化学酶合成方法，可以合成不形成多种笼化化合物的新型笼化NAADP+。在完整的海胆卵子中，笼化NAADP+的快速去笼化证明了其生物活性。

  DOI：

  10.1039/b617344f

文献信息

• Synthesis of photolabile precursors of amino acid neurotransmitters
  作者：Mary Wilcox、Randall W. Viola、Katherine W. Johnson、Andrew P. Billington、Barry K. Carpenter、James A. McCray、Anthony P. Guzikowski、George P. Hess

  DOI：10.1021/jo00292a038

  日期：1990.3
• Caged Quantum Dots
  作者：Gang Han、Taleb Mokari、Caroline Ajo-Franklin、Bruce E. Cohen

  DOI：10.1021/ja804948s

  日期：2008.11.26

  Photoactivatable organic fluorophores and fluorescent proteins have been widely adopted for cellular imaging and have been critical for increasing temporal and spatial resolution, as well as for the development of superresolution microscopy techniques. At the same time, semiconducting nanocrystat quantum dots (QDs) have shown superior brightness and photostability compared to both organic fluorophores and proteins. As part of our efforts to develop nanoparticles with novel optical properties, we have synthesized caged quantum dots, which are nonluminescent under typical microscopic illumination but can be activated with stronger pulses of UV light. We show that ortho-nitrobenzyl groups efficiently quench QDs of different compositions and emissions and can be released from the nanoparticle surface with UV light, both in solution and in live cells. This caging is dependent on the emission of the QD, but it is effective through the visible spectrum into the nIR, offering a large array of new colors for photoactivatable probes. Like organic and protein-based photoactivatable probes, caged QDs can confer increased spatial and temporal resolution, with the added brightness and photostability of QDs.
• A Caged Doxycycline Analogue for Photoactivated Gene Expression
  作者：Sidney B. Cambridge、Daniel Geissler、Sandro Keller、Beate Cürten

  DOI：10.1002/anie.200503339

  日期：2006.3.27
• Chemo-enzymatic synthesis and biological evaluation of photolabile nicotinic acid adenine dinuclotide phosphate (NAADP⁺)
  作者：Raman Parkesh、Sridhar R. Vasudevan、Alexandra Berry、Antony Galione、James Dowden、Grant C. Churchill

  DOI：10.1039/b617344f

  日期：——

  A chemo-enzymatic synthesis of novel caged NAADP+ without the formation of multiple cage compounds has been achieved. The biological activity of the caged NAADP+ was demonstrated by its fast uncaging in intact sea-urchin eggs.

  成功实现了一种新的化学酶合成方法，可以合成不形成多种笼化化合物的新型笼化NAADP+。在完整的海胆卵子中，笼化NAADP+的快速去笼化证明了其生物活性。
• Caged agonist of P2Y1 and P2Y12 receptors for light-directed facilitation of platelet aggregation
  作者：Zhan-Guo Gao、Béatrice Hechler、Pedro Besada、Christian Gachet、Kenneth A. Jacobson

  DOI：10.1016/j.bcp.2007.10.037

  日期：2008.3

  We have prepared a caged form (MRS2703) of a potent dual agonist of the P2Y(1) and P2Y(12) nucleotide receptors, 2-MeSADP, by blocking the p-phosphate group with a 1-(3,4-dimethyloxyphenyl)eth-1-yl phosphoester. Although MRS2703 is itself inactive at human P2Y(1) and P2Y(12) receptors expressed heterologously in 1321N1 astrocytoma cells or in washed human platelets, this derivative readily regenerates the parent agonist upon mild irradiation with long-wave UV light (360 nm). The functional effect of the regenerated agonist was demonstrated by a rise in intracellular calcium mediated by either P2Y(1) or P2Y(12) receptors in transfected cells. Washed human platelets exposed to a solution of MRS2703 were induced to aggregate upon UV irradiation. At 1.0 mu M MRS2703, full aggregation was achieved within 1 min of irradiation. Thus, this caged nucleotide promises to be a useful probe for potent P2Y receptor activation with light-directed spatial and temporal control. Published by Elsevier Inc.