4-(7'-coumarinoxy)-butyric acid | 126051-09-0

• 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
• 英文名称: 4-(7'-coumarinoxy)-butyric acid
• 英文别名: 4-(2-oxo-2H-chromen-7-yloxy)butanoic acid；4-(2-Oxochromen-7-yl)oxybutanoic acid
• CAS: 126051-09-0
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: KVHPPJNUWXHWGS-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  511.7±50.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(7'-coumarinoxy)-butyric acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 27.0h， 生成 N-Octadecyl-4-[10-(3-octadecylcarbamoyl-propoxy)-6,7-dioxo-6,6a,6b,7,12b,12c-hexahydro-5,8-dioxa-dibenzo[a,i]biphenylen-3-yloxy]-butyramide
  参考文献：
  名称：

  Synthesis and properties of coumarin-derived organogelators

  摘要：

  A new family of coumarin derivatives containing amide group with different alkyl chain lengths was synthesized and their properties as organogelators were evaluated. It was found that the organogelation abilities were not obviously affected by the alkyl spacer length of amide group. Helical morphologies formed either in nonpolar or high polar solvents by most of the gelators. Occurrence of reversible and stereoselective photodimerization of the gel formed by 4-(7'-coumarinoxy)-N-octadecylbutanamide (3a) in cyclohexane was confirmed by H-1 NMR, UV absorption, and fluorescence spectra. The photoreaction of the gel proceeded without any dissolution, but the drastic microscopic changes of gel morphologies accompanied with the irradiation were identified using SEM and AFM investigations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.003
• 作为产物：
  描述：

  7-羟基香豆素 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 4-(7'-coumarinoxy)-butyric acid
  参考文献：
  名称：

  N-[(吲哚基)乙基)香豆素-基氧基)]链烷酰胺的合成及抗乙酰胆碱酯酶活性

  摘要：

  合成了通过接头连接的新型香豆素-色胺系统，并通过经典的 Ellman 测试在体外针对乙酰胆碱酯酶进行了评估。

  DOI：

  10.3184/174751917x14859570937677

文献信息

• Synthesis and biological evaluation of CX-659S and its related compounds for their inhibitory effects on the delayed-type hypersensitivity reaction
  作者：Masanori Tobe、Yoshiaki Isobe、Yuso Goto、Fumihiro Obara、Masami Tsuchiya、Junko Matsui、Kosaku Hirota、Hideya Hayashi

  DOI：10.1016/s0968-0896(00)00126-7

  日期：2000.8

  In order to find novel nonsteroidal compounds possessing an inhibitory activity against delayed-type hypersensitivity (DTH) reactions, we conducted random screening using a picryl chloride (PC)-induced contact hypersensitivity reaction (CHR) in mice, and found compound 1 as a lead compound. Then we synthesized and evaluated an extensive series of 5-carboxamidouracil derivatives focused on both the

  为了找到对延迟型超敏反应（DTH）反应具有抑制活性的新型非甾体化合物，我们使用氯化吡啶（PC）诱导的小鼠接触超敏反应（CHR）在小鼠中进行了随机筛选，发现化合物1为铅复合。然后，我们合成并评估了一系列广泛的针对尿嘧啶和抗氧化部分的5-羧酰胺基尿嘧啶衍生物。其中，我们发现受阻酚部分对于展示其活性是必要的。特别地，发现具有维生素E的部分结构的化合物28a-28c通过口服和局部给药都具有针对DTH反应的有效活性。化合物28c对脂质过氧化具有抗氧化活性，IC50为5.9 microM。
• Identification of Small Molecules Blocking the Pseudomonas aeruginosa Type III Secretion System Protein PcrV
  作者：Charlotta Sundin、Michael Saleeb、Sara Spjut、Liena Qin、Mikael Elofsson

  DOI：10.3390/biom11010055

  日期：——

  Pseudomonas aeruginosa is an opportunistic bacterial pathogen that employs its type III secretion system (T3SS) during the acute phase of infection to translocate cytotoxins into the host cell cytoplasm to evade the immune system. The PcrV protein is located at the tip of the T3SS, facilitates the integration of pore-forming proteins into the eukaryotic cell membrane, and is required for translocation of cytotoxins into the host cell. In this study, we used surface plasmon resonance screening to identify small molecule binders of PcrV. A follow-up structure-activity relationship analysis resulted in PcrV binders that protect macrophages in a P. aeruginosa cell-based infection assay. Treatment of P. aeruginosa infections is challenging due to acquired, intrinsic, and adaptive resistance in addition to a broad arsenal of virulence systems such as the T3SS. Virulence blocking molecules targeting PcrV constitute valuable starting points for development of next generation antibacterials to treat infections caused by P. aeruginosa.

  铜绿假单胞菌是一种机会性细菌病原体，它在感染的急性阶段利用其III型分泌系统（T3SS）将细胞毒素转运到宿主细胞胞质中，以逃避免疫系统。PcrV蛋白位于T3SS的顶端，促进孔形成蛋白与真核细胞膜的整合，并且需要将细胞毒素转运到宿主细胞中。在这项研究中，我们使用表面等离子共振筛选识别PcrV的小分子结合物。随后进行的结构-活性关系分析得出了能在基于P. aeruginosa细胞的感染实验中保护巨噬细胞的PcrV结合物。治疗P. aeruginosa感染具有挑战性，因为除了广泛的毒力系统（如T3SS）外，还存在获得性、固有性和适应性抗性。针对PcrV的毒力阻断分子为开发下一代抗菌剂治疗由铜绿假单胞菌引起的感染提供了宝贵的起点。
• Synthesis and antitumor study of novel porphyrin–coumarin derivatives for chemotherapy and photodynamic therapy
  作者：Zejie Tian、Lei Shi、Zhenhua Liu、Hui Li、Lingyan Yang、Yunmei Liu

  DOI：10.1016/j.molstruc.2023.135826

  日期：2023.9

  Photodynamic therapy (PDT) is attractive in cancer treatment because of its non-invasive and low side effects. In this study, we synthesized 20 porphyrin–coumarin compounds via condensation reactions of porphyrins with coumarin derivatives. In the singlet oxygen (1O2) assay, DPBF fluorescence was quenched by 85% after 10 s of light irradiation; the fluorescence of DPBF almost disappeared at 30 s by

  光动力疗法 (PDT) 因其无创和低副作用而在癌症治疗中具有吸引力。在这项研究中，我们通过卟啉与香豆素衍生物的缩合反应合成了 20 种卟啉-香豆素化合物。在单线态氧( 1 O 2 )测定中，DPBF荧光在光照10 s后猝灭85%；DPBF的荧光在光照30 s时几乎消失。这表明卟啉-香豆素类化合物具有优异的1 O 2发电效率。此外，卟啉-香豆素化合物在光照下对A549和HepG2细胞表现出不同的抑制作用。而在黑暗条件下，具有较短烷基链的化合物显示出抗肿瘤活性，而支链和烷基链的延伸降低了化合物的活性。因此，将具有较短烷基链的香豆素衍生物接入卟啉可实现PDT和化学疗法。此外，金属锌插入卟啉也增强了化合物的光动力治疗效果。
• Template-directed photoligation
  申请人：AMOCO CORPORATION

  公开号：EP0324616A2

  公开（公告）日：1989-07-19

  Methods, apparatus and compositions are presented for ligating ligands together which bind to a common target. One embodiment includes polynucleotide probes having pho­toreactive functional groups. The probes are capable of assuming substantially contiguous reactive positions on a target polynucleotide placing the photoreactive groups in juxtaposition. Activation of the photoreactive functional groups with radiant energy form a probe reaction product in which the probes are bound to each other.

  本文介绍了将与共同目标结合的配体连接在一起的方法、装置和组合物。其中一个实施方案包括具有光活性官能团的多核苷酸探针。这些探针能够在目标多核苷酸上占据基本连续的反应位置，并将光活性基团并置。光活性官能团在辐射能的激活下形成探针反应产物，其中的探针相互结合。
• Synthesis and anti-cholinesterase activity of new 7-hydroxycoumarin derivatives
  作者：Masoumeh Alipour、Mehdi Khoobi、Alireza Moradi、Hamid Nadri、Farshad Homayouni Moghadam、Saeed Emami、Zeinab Hasanpour、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2014.05.056

  日期：2014.7

  A series of 7-hydroxycoumarin derivatives connected by an amidic linker to the different amines were designed and synthesized as cholinesterase inhibitors. Most compounds showed remarkable inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Among them, N-(1-benzylpiperidin-4-yl)acetamide derivative 4r with IC50 value of 1.6 mu M was the most potent compound against AChE. The selectivity index of compound 4r for anti-AChE activity was about 26. Moreover, the compound 4r significantly protected PC12 neurons against H2O2-induced cell death at low concentrations. The docking study of compound 4r with AChE enzyme showed that both CAS and PAS are occupied by the ligand. (C) 2014 Elsevier Masson SAS. All rights reserved.