4-(7'-coumarinoxy)-butyric acid ethyl ester | 75929-27-0

• 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 ethyl ester
• 英文别名: 7-carbethoxy-n-propyloxycoumarin；Ethyl 4-(2-oxochromen-7-yl)oxybutanoate
• CAS: 75929-27-0
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: SWLIQMIRSYRXHK-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  447.2±45.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(7'-coumarinoxy)-butyric acid ethyl ester 在 氢氧化钾 、 水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 4-(7'-coumarinoxy)-N-octadecylbutanamide
  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 、 4-溴丁酸乙酯 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 生成 4-(7'-coumarinoxy)-butyric acid ethyl ester
  参考文献：
  名称：

  用于化疗和光动力治疗的新型卟啉-香豆素衍生物的合成及抗肿瘤研究

  摘要：

  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。

  DOI：

  10.1016/j.molstruc.2023.135826

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。
• Synthesis and Anti-Acetylcholinesterase Activity of N-[(indolyl)ethyl)-coumarin-yloxy)]Alkanamides
  作者：Sarah Ghanei-Nasab、Hamid Nadri、Alireza Moradi、Azam Marjani、Shabnam Shabani、Loghman Firoozpour、Setareh Moghimi、Mehdi Khoobi、Farzin Hadizadeh、Alireza Foroumadi

  DOI：10.3184/174751917x14859570937677

  日期：2017.2

  Novel coumarin–tryptamine systems attached through a linker were synthesised and evaluated in vitro against acetylcholinesterase by the classical Ellman's test.

  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。
• 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。
• Bicyclic carboxylic acid derivatives as anti-inflammatory agents
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0531823A1

  公开（公告）日：1993-03-17

  Compounds of the formula    wherein    X is -O- or -CH₂-;    Y is -O-, -CH₂-CH₂-, -CH=CH-, -C≡C- or -OCH₂C₆H₄-;    Z is -CH₂-CH₂-, -CH=CH- or -C≡C-;    R¹ is hydrogen, lower alkyl, lower alkenyl, cycloalkyl or aralkyl;    A is -B or -O-B;    B is a mono-, di- or tricyclic aromatic or heteroaromatic moiety substituted by the group -COR², -(O)t-(W)s-COR²or -(CH=CH)pCOR² and which may also contain up to 4 additional substituents selected, independently, from the group consisting of halogen, cyano, lower alkyl, lower alkoxy, sulfonamido, alkanoyl, aroyl, -(Q)k-(W)s'-E or -(Q)k-(W)s''-    C₆H₄-(W)s'''-E, provided that no more than one of said substituents is -(Q)k-(W)s'-E or -(Q)k-(W)s''-C₆H₄-(W)s'''-E;    E is -COR² or R²;    W is -CR³R⁴-;    Q is -O- or carbonyl;    R² is hydroxy, lower alkoxy or -NR³R⁴;    R³ and R⁴ , each occurence, independently, are hydrogen or lower alkyl;    f, h, k, m and t, independently, are 0 or 1;    n, s and s', independently, are an integer from 1 to 12;    p is an integer from 1 to 2;    s'' and s''', independently, are a integer from 0 to 12; and    C₆H₄ is a 1,2-, 1,3- or 1,4-phenylene moiety, their geometric and optical isomers and, when R² hydroxy, pharmaceutically acceptable salts thereof with bases are potent leukotriene B₄ antagonists and are therefore useful in the treatment of inflammatory diseases, such as psoriasis, inflammatory bowel diseases, asthma, allergy, arthritis, dermatitis, gout, pulmonary disease, ischemia/reperfusion injury, and trauma induced inflammation, such as spinal cord injury.

  式中的化合物 其中 X 是-O-或-CH₂-； Y 是-O-、-CH₂-CH₂-、-CH=CH-、-C≡C- 或-OCH₂C₆H₄-； Z 是 -CH₂-CH₂-、-CH=CH- 或 -C≡C-； R¹ 是氢、低级烷基、低级烯基、环烷基或芳烷基； A 是-B 或-O-B； B 是被基团-COR²、-(O)t-(W)s-COR²或-(CH=CH)pCOR²取代的单环、二环或三环芳香族或杂芳族分子，其中还可包含最多 4 个独立选自卤素、氰基、低级烷基、低级烷氧基、磺酰胺基、烷酰基、芳基、-(Q)k-(W)s'-E 或-(Q)k-(W)s''-的额外取代基。 (Q)k-(W)s''-E或-(Q)k-(W)s''-C₆H₄-(W)s''-E； E 是 -COR² 或 R²； W 是-CR³R⁴-； Q 是-O-或羰基； R² 是羟基、低级烷氧基或-NR³R⁴； R³ 和 R⁴，各自独立地为氢或低级烷基； f、h、k、m 和 t 独立地为 0 或 1； n、s 和 s' 分别是 1 到 12 的整数； p 是 1 到 2 的整数； s'' 和 s'''' 分别是 0 至 12 的整数；以及 C₆H₄ 是 1,2-、1,3- 或 1,4- 苯基、 它们的几何异构体和光学异构体，以及当 R² 为羟基时，它们与碱的药学上可接受的盐是强效的白三烯 B₄拮抗剂，因此可用于治疗炎症性疾病，如牛皮癣、炎症性肠病、哮喘、过敏、关节炎、皮炎、痛风、肺部疾病、缺血/再灌注损伤和创伤引起的炎症，如脊髓损伤。
• 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.