(perylen-3-yl)methyl propargyl ether | 877642-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (perylen-3-yl)methyl propargyl ether
• 英文别名: 3-(Prop-2-ynoxymethyl)perylene
• CAS: 877642-81-4
• 化学式: C₂₄H₁₆O
• 分子量: 320.39
• InChiKey: RSRCSHDZXBVBBU-UHFFFAOYSA-N

物化性质

• 熔点：
  168-169 °C(Solv: toluene (108-88-3); hexane (110-54-3))
• 沸点：
  544.6±25.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (perylen-3-yl)methyl propargyl ether 在 四(三苯基膦)钯 copper(l) iodide 、 triethylamine trihydrofluoride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 5-{3-[(perylen-3-yl)methoxy]prop-1-ynyl}-2'-deoxyuridine
  参考文献：
  名称：

  5-Alkynyl-2′-deoxyuridines, containing bulky aryl groups: evaluation of structure–anti-HSV-1 activity relationship

  摘要：

  Four 5-alkynyl-2-deoxyuridines containing different bulky substituents and flexible linkers between the triple bond and the aromatic residue have been prepared and tested against HSV-1 in Vero cells. Two nucleosides containing carbonyl groups, 5-(4-benzoylphenoxypropyn-1-yl)-2'-deoxyutidine (19a) and 5-(estron-3-yloxypropyn-1-yl)-2'-deoxyuridine (19c), showed low cytotoxicity and moderate antiviral activity. The flexible linker appears not to be favorable for antiviral properties of 5-alkynyl-2'deoxyuridines: 5-[(perylen-3-yl)methoxypropyn-1-yl]-2'-deoxyuridine (19d) showed considerable cytotoxicity and no antiviral activity in contrast to the active and nontoxic 5-(perylen-3-ylethynyl)-2'-deoxyuridine (9), a nucleoside with a rigid triple-bond-connection of the aromatic system to the nucleobase. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.057
• 作为产物：
  描述：

  苝 在 lithium aluminium tetrahydride 、 18-冠醚-6 、 potassium hydroxide 、 三氯化磷 作用下， 以 四氢呋喃 、 水 、 邻二氯苯 为溶剂， 反应 5.5h， 生成 (perylen-3-yl)methyl propargyl ether
  参考文献：
  名称：

  能量下转换的有机荧光团官能化的介孔二氧化硅杂化物，用于整体涂覆的发光二极管。

  摘要：

  本文报道了在不使用无机过渡或稀土金属的情况下，有机荧光团在介孔二氧化硅基质中的共价结合，用作能量向下转换的磷光体。合成了蓝色发光的ylene，绿色发光的苯并呋喃烷和红色发光的尼罗红的三乙氧基甲硅烷基丙基取代的衍生物，并通过后接枝到市售MCM-41上，用于介孔杂化材料的合成。将这些经过单独染料官能化的杂化材料以可变的比例混合，以提供一种粉末，该粉末在410 nm照射时能发出CIE色度坐标为x = 0.33，y = 0.33和外部量子产率为4.6％的白光。此外，作为概念验证，市售UV发光二极管有两种不同的设备设置，用含有三种三乙氧基甲硅烷基丙基取代的荧光团衍生物的硅石整体涂层。这些涂层能够将发出的UV光转换为具有非常冷的白色（41100 K，10700 K）的相关色温以及具有相关的色温大约5500 K的绿色白色发射光。

  DOI：

  10.3762/bjoc.13.76

文献信息

• Oligosaccharide conjugates for targeting bacteria and uses related thereto
  申请人：Emory University

  公开号：US09821071B2

  公开（公告）日：2017-11-21

  This disclosure relates to conjugates for targeting bacteria and related uses. In certain embodiments, the disclosure relates to methods of transferring a molecule of interest into bacteria comprising mixing bacteria with a non-naturally occurring conjugate under conditions such that the conjugate is transported across the bacterial cell wall. Typically, the conjugate comprises an oligosaccharide and a molecule of interest. In certain embodiments, the molecule of interest may be a tracer or an antibiotic.

  这份披露涉及用于靶向细菌和相关用途的共轭物。在某些实施例中，该披露涉及将感兴趣的分子转移至细菌的方法，包括将细菌与非自然存在的共轭物混合在一起，在条件下使共轭物被跨越细菌细胞壁。通常，共轭物包括寡糖和感兴趣的分子。在某些实施例中，感兴趣的分子可能是示踪剂或抗生素。
• Maltodextrin-based imaging probes detect bacteria in vivo with high sensitivity and specificity
  作者：Xinghai Ning、Seungjun Lee、Zhirui Wang、Dongin Kim、Bryan Stubblefield、Eric Gilbert、Niren Murthy

  DOI：10.1038/nmat3074

  日期：2011.8

  The in vivo optical detection of bacterial infections requires highly specific imaging probes with small affinity to mammalian tissue. It is now shown that fluorescent dyes that are conjugated to maltohexaose can be internalized rapidly via the bacteria-specific maltodextrin transport pathway, enabling the in vivo imaging of Escherichia coli down to 105 colony-forming units. The diagnosis of bacterial infections remains a major challenge in medicine. Although numerous contrast agents have been developed to image bacteria, their clinical impact has been minimal because they are unable to detect small numbers of bacteria in vivo, and cannot distinguish infections from other pathologies such as cancer and inflammation1,2,3,4,5,6,7. Here, we present a family of contrast agents, termed maltodextrin-based imaging probes (MDPs), which can detect bacteria in vivo with a sensitivity two orders of magnitude higher than previously reported, and can detect bacteria using a bacteria-specific mechanism that is independent of host response and secondary pathologies. MDPs are composed of a fluorescent dye conjugated to maltohexaose, and are rapidly internalized through the bacteria-specific maltodextrin transport pathway8,9,10,11, endowing the MDPs with a unique combination of high sensitivity and specificity for bacteria. Here, we show that MDPs selectively accumulate within bacteria at millimolar concentrations, and are a thousand-fold more specific for bacteria than mammalian cells. Furthermore, we demonstrate that MDPs can image as few as 105 colony-forming units in vivo and can discriminate between active bacteria and inflammation induced by either lipopolysaccharides or metabolically inactive bacteria.

  细菌感染的体内光学检测需要对哺乳动物组织具有较小亲和力的高度特异性成像探针。现在表明，与麦芽六糖结合的荧光染料可以通过细菌特异性麦芽糖糊精转运途径快速内化，从而能够对低至 105 个菌落形成单位的大肠杆菌进行体内成像。细菌感染的诊断仍然是医学上的重大挑战。尽管已开发出多种造影剂来对细菌进行成像，但它们的临床影响微乎其微，因为它们无法检测体内少量细菌，并且无法区分感染与癌症和炎症等其他病变1,2,3,4,5 ,6,7。在这里，我们提出了一系列造影剂，称为基于麦芽糖糊精的成像探针（MDP），它可以检测体内细菌，其灵敏度比之前报道的高两个数量级，并且可以使用细菌特异性机制检测细菌，即独立于宿主反应和继发性病理。 MDP 由与麦芽六糖缀合的荧光染料组成，并通过细菌特异性麦芽糖糊精转运途径快速内化8,9,10,11，赋予MDP 对细菌高灵敏度和特异性的独特组合。在这里，我们证明 MDP 以毫摩尔浓度在细菌内选择性积累，并且对细菌的特异性比哺乳动物细胞高一千倍。此外，我们证明 MDP 可以对体内少至 105 个菌落形成单位进行成像，并且可以区分活性细菌和由脂多糖或代谢不活跃的细菌引起的炎症。
• [EN] SACCHARIDE ANALOGS AND AGENTS FOR THE DIAGNOSIS AND THERAPY OF BACTERIAL INFECTIONS<br/>[FR] ANALOGUES DE SACCHARIDE ET AGENTS POUR LE DIAGNOSTIC ET LA THÉRAPIE D'INFECTIONS BACTÉRIENNES
  申请人：UNIV EMORY

  公开号：WO2016044846A1

  公开（公告）日：2016-03-24

  This disclosure relates saccharide analogs such as thiomaltose-based analogs for targeting bacteria and related uses. In certain embodiments, the disclosure relates to methods of transferring a molecule of interest into bacteria comprising mixing bacteria with a non-naturally occurring conjugate, wherein the conjugate comprises a thiomaltose-based analog and a molecule of interest under conditions such that the conjugate is transported across the bacterial cell wall. In certain embodiments, the molecule of interest can be a tracer or an antibiotic.

  本公开涉及糖类类似物，例如基于硫代麦芽糖的类似物，用于靶向细菌和相关用途。在某些实施例中，本公开涉及将感兴趣的分子转移至细菌的方法，包括将细菌与非自然的共轭物混合，其中该共轭物包括基于硫代麦芽糖的类似物和感兴趣的分子，在条件下进行混合，使共轭物被跨越细菌细胞壁。在某些实施例中，感兴趣的分子可以是示踪剂或抗生素。
• SYNTHESIS AND EVALUATION OF ANTI-HSV ACTIVITY OF NEW 5-ALKYNYL-2′-DEOXYURIDINES
  作者：A. A. Pchelintseva、M. V. Skorobogatyj、A. L. Petrunina、V. L. Andronova、G. A. Galegov、I. V. Astakhova、A. V. Ustinov、A. D. Malakhov、Vladimir A. Korshun

  DOI：10.1081/ncn-200059280

  日期：2005.4.1

  Eight 5-alkynyl-2'deoxyuridines containing different bulky substituents have been prepared and tested against HSV-1 in Vero cells. The compounds show positive antiviral activity. There is no obvious correlation between activity and substituent size. The nature of the linker between uracil and a substituent appears to be more important for antiviral properties: nucleosides containing arylethynyl groups show higher activity.
• Assembly and Exchange of Resorcinarene Capsules Monitored by Fluorescence Resonance Energy Transfer
  作者：Elizabeth S. Barrett、Trevor J. Dale、Julius Rebek

  DOI：10.1021/ja0700956

  日期：2007.4.1

  Resorcinarenes were functionalized with fluorophores and fluorescence resonance energy transfer (FRET) was employed as a tool to probe the dynamic behavior of hydrogen-bonded hexameric assemblies at nanomolar concentrations. The encapsulation of a fluorescent guest inside the capsule made it possible to observe FRET across the mechanical boundary of the hexameric assembly.