香豆素-3-羧酸琥珀酰亚胺酯 | 148627-84-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 香豆素-3-羧酸琥珀酰亚胺酯
• 英文名称: 2,5-dioxopyrrolidin-1-yl 2-oxo-2H-chromene-3-carboxylate
• 英文别名: Coumarin-3-carboxylic acid succinimidyl ester；(2,5-dioxopyrrolidin-1-yl) 2-oxochromene-3-carboxylate
• CAS: 148627-84-3
• 化学式: C₁₄H₉NO₆
• 分子量: 287.229
• InChiKey: NTXGVUJAUMMHQO-UHFFFAOYSA-N

物化性质

• 溶解度：
  在DMF中可溶

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-amino-2-hydroxypropyl)-3-(2-hydroxy-2,2-diphosphonoethyl)pyridinium 、 香豆素-3-羧酸琥珀酰亚胺酯 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 [1-Hydroxy-2-[1-[2-hydroxy-3-[(2-oxochromene-3-carbonyl)amino]propyl]pyridin-1-ium-3-yl]-1-phosphonoethyl]phosphonic acid
  参考文献：
  名称：

  Novel fluorescent risedronates: Synthesis, photodynamic inactivation and imaging of Bacillus subtilis

  摘要：

  Novel fluorescently-labeled conjugates of risedronate were synthesized using an epoxide linker, enabling conjugation of risedronate via its pyridyl nitrogen with the aromatic succinimidyl esters. The compounds were characterized by using H-1 NMR, C-13 NMR, P-31 NMR, UV-vis and fluorescence emission spectroscopies. Biological activity assays showed that the conjugates 14 and 15 exhibited photodynamic inactivation of Bacillus subtilis (ATCC 6633) with 91% and 47% bacterial lethality at 10 mu M upon visible light irradiation, respectively. Both 14 and 15 could be also used for fluorescence imaging of Bacillus subtilis. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.051
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 香豆素-3-羧酸 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以52%的产率得到香豆素-3-羧酸琥珀酰亚胺酯
  参考文献：
  名称：

  一种方便的AIE荧光探针，适用于广泛的pH检测。

  摘要：

  pH的检测在各个领域越来越受到关注。当前，一个热门的研究主题集中在如何使用一种简便的荧光染料来实现广泛而准确的pH检测。本文中，我们报告了一种基于聚集诱导排放（AIE）特性的，用于pH检测的简单荧光探针，具有广泛的范围和准确性。由香豆素和喹啉作为电子供体和受体的探针2-oxo-N'-（2-（quinolin-8-yloxy）acetyl）-2H-chromne-3-carbo-hydrazide（CHBQ），N，N '-二甲酰肼键分别作为连接基团。在混合介质中含水量高达99％的情况下，该探头显示出良好的AIE特性。此外，通过在UV365 nm灯下改变溶液的颜色，它可以在30 s内快速识别酸和碱。pH探针的检测几乎不干扰其他离子。而且，CHBQ探针可以设计成广泛的pH检测试纸，具有很大的实用价值。

  DOI：

  10.1016/j.saa.2019.117650

文献信息

• COMPOSITIONS AND METHODS FOR TREATMENT OF VIRAL DISEASES
  申请人：Johansen Lisa M.

  公开号：US20100009970A1

  公开（公告）日：2010-01-14

  The present invention features compositions, methods, and kits useful in the treatment of viral diseases. In certain embodiments, the viral disease is caused by a single stranded RNA virus, a flaviviridae virus, or a hepatic virus. In particular embodiments, the viral disease is viral hepatitis (e.g., hepatitis A, hepatitis B, hepatitis C, hepatitis D, hepatitis E) and the agent or combination of agents includes sertraline, a sertraline analog, UK-416244, or a UK-416244 analog. Also featured are screening methods for identification of novel compounds that may be used to treat a viral disease.

  本发明涉及用于治疗病毒性疾病的组合物、方法和试剂盒。在某些实施方式中，病毒性疾病是由单链RNA病毒、黄病毒科病毒或肝病毒引起的。在特定实施方式中，病毒性疾病是病毒性肝炎（例如甲型肝炎、乙型肝炎、丙型肝炎、丁型肝炎、戊型肝炎），药剂或药剂组合包括舍曲林、舍曲林类似物、UK-416244或UK-416244类似物。还包括用于鉴定可用于治疗病毒性疾病的新化合物的筛选方法。
• Flow-based bioconjugation of coumarin phosphatidylethanolamine probes: Optimised synthesis and membrane molecular dynamics studies
  作者：Pedro A.M.M. Varandas、Ricardo Belinha、Alexander J.A. Cobb、João P. Prates Ramalho、Marcela A. Segundo、Luís M.S. Loura、Eduarda M.P. Silva

  DOI：10.1016/j.bbamem.2024.184335

  日期：2024.10

  of the behaviour of a representative probe of this family, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine labelled with 3-carboxycoumarin (POPE-COUM), in bilayers of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC)/1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine (SLPC) 2:1, mimicking the composition of the egg yolk lecithin membranes recently used experimentally by our group to study

  通过连续流合成，通过改进的生物偶联方法制备了一系列用 3-羧基香豆素标记的头部标记的磷脂酰乙醇胺荧光探针。与传统的批量方法相比，既定程序在实验设计 （DoE） 设置的支持下，除了略微提高产量外，还显著缩短了反应时间。通过对该家族代表性探针的行为进行深入的分子动力学 （MD） 研究，即用 3-羧香豆素 （POPE-COUM） 标记的 1-棕榈酰-2-油酰-sn-甘油-3-磷酸乙醇胺，在 1-棕榈酰-2-油酰-sn-甘油-3-磷酸胆碱 （POPC）/1-硬脂酰-2-亚油酰-sn-甘油-3-磷酸胆碱 （SLPC） 2：1 的双层中，模拟了我们小组最近实验研究的蛋黄卵磷脂膜的组成POPE-COUM 作为大单层囊泡 （LUV） 氧化态和完整性的生物标志物。MD 模拟显示香豆素基团朝向双层内部，导致相对内部的位置，这与在商业头部标记的 NBD-PE 探针的硝基苯并恶二唑荧光团中观察到的情况一致。这种行为与前面陈述的假设一致，即
• Sialyltransferase inhibitors: consideration of molecular shape and charge/hydrophobic interactions
  作者：Rishi Kumar、Ravindranath Nasi、Milan Bhasin、Nam Huan Khieu、Margaret Hsieh、Michel Gilbert、Harold Jarrell、Wei Zou、Harold J. Jennings

  DOI：10.1016/j.carres.2012.12.017

  日期：2013.8

  In order to evaluate the importance of molecular shape of inhibitor molecules and the charge/H-bond and hydrophobic interactions, we synthesized three types of molecules and tested them against a sialyltransferase. The first type of compounds were designed as substrate mimics in which the phosphate in CMP-Neu5NAc was replaced by a non-hydrolysable, uncharged 1,2,3-triazole moiety. The second type of compound contained a 2-deoxy-2,3-dehydro-acetylneuraminic moiety which was linked to cytidine through its carboxylic acid and amide linkers. In the third type of compound the sialyl phosphate was substituted by an aryl sulfonamide which was then linked to cytidine. Inhibition study of these cytidine conjugates against Campylobacter jejuni sialyltransferase Cst 06 showed that the first type of molecules are competitive inhibitors, whereas the other two could only inhibit the enzyme non-competitively. The results indicate that although the binding specificity may be guided by molecular shape and H-bond interaction, the charge and hydrophobic interactions contributed most to the binding affinity. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.
• Fluorescent head-labelled phospholipid coumarin bioconjugate as a chemical reporter for antioxidant protection in liposomes
  作者：Pedro A.M.M. Varandas、Ricardo Belinha、Sara S. Marques、Alexander J.A. Cobb、Vanda Vaz Serra、Marcela A. Segundo、Eduarda M.P. Silva

  DOI：10.1016/j.dyepig.2023.111440

  日期：2023.10
• HAPTENS, HAPTEN CONJUGATES, COMPOSITIONS THEREOF AND METHOD FOR THEIR PREPARATION AND USE
  申请人：Ventana Medical Systems, Inc.

  公开号：EP3029461B1

  公开（公告）日：2017-12-20