2-(N-acetylamino)-7-(bromomethyl)-1,8-naphthyridine | 120927-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(N-acetylamino)-7-(bromomethyl)-1,8-naphthyridine
• 英文别名: 2-(acetylamino)-7-(bromomethyl)-1,8-naphthyridine；2-bromomethyl-7-acetylamino-1,8-naphthyridine；N-(7-Bromomethyl-[1,8]naphthyridin-2-yl)-acetamide；N-[7-(bromomethyl)-1,8-naphthyridin-2-yl]acetamide
• CAS: 120927-25-5
• 化学式: C₁₁H₁₀BrN₃O
• 分子量: 280.124
• InChiKey: OHFINMXFQDVUQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(N-acetylamino)-7-(bromomethyl)-1,8-naphthyridine 在 sodium perchlorate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  A water-soluble 1,8-naphthyridine-based imidazolium molecular gripper for fluorescence sensing and discriminating of GMP

  摘要：

  A selective receptor for sensing and discriminating of GMP is useful not only in the energy metabolism but also in the processes of DNA replication and transcription-related to GMP; such a receptor is presently rare especially in a pure water environment. Herein, a novel 1,8-naphthyridine-based tripodal imidazolium gripper-like molecular served as a "turn-on" fluorescent receptor (TINP) was designed and synthesized for selective sensing and discriminating GMP from structurally similar GNPs (N = D and T) and XMPs (X = U, T, A, and C) in 100% aqueous solution. TINP consists of 1,8-naphthyridines and imidazolium cations. 2-acetylamino-1,8-naphthyridine was chosen as fluorophore and tri-hydrogen bonds interactions sites for the nucleobase guanine. Imida-zolium cations were identified as the phosphate part receiving moieties and communicators, while the three imidazolium cations also served as indispensable water-soluble parts. GMP caused a remarkable fluorescence enhancement (ca. 6.5-fold) with a quantum yield (Phi(f)) of 0.26 at 399 nm, displaying an efficient "turn on" behavior. The sensing mechanisms and fluorescence response were explained by Job's plot, NMR spectroscopic analysis, and theoretical calculations. The "turn-on" fluorescent property for GMP can be attributed to photoinduced electron transfer (PeT) transitions with some mixed intraligand charge-transfer (ILCT) transitions. Finally, the preliminary results of cell experiments show that the receptor can be applied for the imaging of GMP in living mammalian cells.

  DOI：

  10.1016/j.dyepig.2019.108103
• 作为产物：
  描述：

  2-氨基-7-甲基-1,8-萘啶 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 2-(N-acetylamino)-7-(bromomethyl)-1,8-naphthyridine
  参考文献：
  名称：

  Ross Kelly; Bridger, Gary J.; Zhao, Chen, Journal of the American Chemical Society, 1990, vol. 112, # 22, p. 8024 - 8034

  摘要：

  DOI：

文献信息

• <i>N</i>-bromosuccinimide reactions of some heterocycles in the presence or absence of water: An overview of ring versus side chain bromination for the synthesis of important brominated heterocyclic synthons
  作者：Shyamaprosad Goswami、Kumaresh Ghosh、Reshmi Mukherjee、Avijit Kumar Adak、Ajit Kumar Mahapatra

  DOI：10.1002/jhet.5570380125

  日期：2001.1

  Reactions of various heterocycles 1–6 with N-bromosuccinimide in the presence or absence of water have been studied for side chain versus ring bromination to afford some new and important heterocyclic synthons. Interestingly, the N-bromosuccinimide reaction in the presence of perchloric acid, a new condition, affords exclusively the new dibromo aminopicoline 1f, which is not obtained by other presently

  对于侧链与环溴化反应，研究了各种杂环1-6与N-溴琥珀酰亚胺在有水或无水条件下的反应，以提供一些新的重要的杂环合成子。有趣的是，在高氯酸存在下的N-溴琥珀酰亚胺反应（一种新条件）仅提供了新的二溴氨基吡啶1f，这是目前其他研究方法无法获得的。
• Side Chain Bromination of Mono and Dimethyl Heteroaromatic and Aromatic Compounds by Solid Phase<i>N</i>-Bromosuccinimide Reaction without Radical Initiator under Microwave
  作者：Shyamaprosad Goswami、Swapan Dey、Subrata Jana、Avijit Kumar Adak

  DOI：10.1246/cl.2004.916

  日期：2004.7

  A series of side chain mono and dibromo derivatives of mono and dimethyl heteroaromatic and aromatic compounds (1–17) were synthesized by one step solid phase N-bromosuccinimide (NBS) reaction with...

  通过一步固相 N-溴代琥珀酰亚胺 (NBS) 反应合成了一系列单和二甲基杂芳族和芳族化合物 (1-17) 的侧链单和二溴衍生物。
• A bisubstrate reaction template
  作者：T. Ross Kelly、Chen Zhao、Gary J. Bridger

  DOI：10.1021/ja00192a039

  日期：1989.5
• Naphthyridine-based symmetrical and unsymmetrical pyridinium amides in sensing of biotin salt
  作者：Kumaresh Ghosh、Avik Ranjan Sarkar、Tanushree Sen

  DOI：10.1080/10610270903089738

  日期：2010.2.1

  Two naphthyridine-based receptors have been designed and synthesised for biotin salt. The compounds serve as good hosts for the detection of biotin carboxylate rather than biotin ester. The correct dispositions of the binding groups under an isophthaloyl spacer enable the receptors to bind both the cyclic urea and the carboxylate ends simultaneously with moderate binding constant values. The receptors are effective for the binding of tetrabutylammonium salt of biotin with a concomitant increase in the fluorescence of naphthyridine and show appreciable binding of biotin salt in CH3CN containing 1.2% DMSO. The binding was monitored in CH3CN containing 1.2% DMSO and DMSO using H-1 NMR, UV-vis and fluorescence spectroscopic methods.
• KELLY, T. ROSS;BRIDGER, GARY J.;ZHAO, CHEN, J. AMER. CHEM. SOC., 112,(1990) N2, C. 8024-8034
  作者：KELLY, T. ROSS、BRIDGER, GARY J.、ZHAO, CHEN

  DOI：——

  日期：——