3-acetamido-2-oxo-2H-chromen-7-yl acetate | 69019-75-6

• 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: 3-acetamido-2-oxo-2H-chromen-7-yl acetate
• 英文别名: (3-Acetamido-2-oxochromen-7-yl) acetate
• CAS: 69019-75-6
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: OBDYUBVEBKAGNI-UHFFFAOYSA-N

物化性质

• 熔点：
  242 °C
• 沸点：
  533.3±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetamido-2-oxo-2H-chromen-7-yl acetate 在 盐酸 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 25.42h， 生成 3-{4-[4-((7α,17β)-3,17-dihydroxyestra-1,3,5(10)-trien-7-yl)-butyl]-1,2,3-triazol-1-yl}-7-hydroxy-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of Novel Estrogen Receptor Antagonists Using Metal-Catalyzed Coupling Reactions and Characterization of Their Biological Activity

  摘要：

  Estrogen receptor (ER) antagonists are valuable in the treatment of ER-positive human breast cancer. In this study, we designed and synthesized nine new derivatives of 17 beta-estradiol (E-2) with a bulky side chain attached to its C-7 alpha position, and determined their ER antagonistic activity using in vitro bioassays. Four of the derivatives showed a strong inhibition of ER alpha transactivation activity in a luciferase reporter assay and blocked ER alpha interactions with coactivators. Similarly, these derivatives also strongly inhibited the growth of the ER alpha-positive human breast cancer cells. Computational docking analysis was conducted to model the interaction of these antagonists with the human ER alpha and showed that they could tightly bind to the ER alpha in a manner similar to that of ICI-182,780, a pure ER antagonist. These results provide an example that attachment of a bulky side chain to the C-7 alpha position of E-2 can produce ER antagonists with ER affinity comparable to that of ICI-182, 780.

  DOI：

  10.1021/jm3013773
• 作为产物：
  描述：

  N-乙酰甘氨酸 、 2,4-二羟基苯甲醛 在 sodium acetate 、 乙酸酐 作用下， 反应 4.0h， 以34%的产率得到3-acetamido-2-oxo-2H-chromen-7-yl acetate
  参考文献：
  名称：

  High Spatiotemporal Control of Spontaneous Reactions Using Ultrasound-Triggered Composite Droplets

  摘要：

  Achieving high spatial and temporal control over a spontaneous reaction is a particularly challenging task with potential breakthroughs in various fields of research including surface patterning and drug delivery. We report here an exceptionally effective method that allows attaining such control. This method relies on a remotely triggered ultrasound-induced release of a reactant encapsulated in a composite microdroplet of liquid perfluorohexane. More specifically, the demonstration was achieved by locally applying a focused 2.25 MHz transducer onto a microfluidic channel in which were injected composite microdroplets containing a solution of an azidocoumarin and an external flow containing a reactive alkyne.

  DOI：

  10.1021/ja5019354

文献信息

• NOVOBIOCIN ANALOGUES AND TREATMENT OF POLYCYSTIC KIDNEY DISEASE
  申请人：Calvet James P.

  公开号：US20110082098A1

  公开（公告）日：2011-04-07

  Novobiocin analogues are useful in methods of treating, inhibiting, and/or preventing cyst formation in autosomal dominant polycystic kidney disease (ADPKD) in a subject. The disclosure provides methods of treating ADPKD comprising administering a therapeutically effective amount of a coumarin-3-carboxamide novobiocin analogue. Accordingly, the method can include administering a novobiocin analogue in a therapeutically effective amount for reducing levels of mTOR pathway phosphoproteins P-mTOR, P-Akt and P-S6K, or combinations thereof. Further, the method can include administering a novobiocin analogue in a therapeutically effective amount for reducing levels of Hsp-90 client proteins CFTR, ErbB2, c-Raf and Cdk4, or combinations thereof.

  新比奴霉素类似物在治疗、抑制和/或预防自体显性多囊肾病（ADPKD）中的囊肿形成方法中是有用的。本公开提供了治疗ADPKD的方法，包括给予香豆素-3-羧酰胺新比奴霉素类似物的治疗有效量。因此，该方法可以包括给予新比奴霉素类似物的治疗有效量，以降低mTOR途径磷酸化蛋白P-mTOR、P-Akt和P-S6K的水平，或其组合。此外，该方法可以包括给予新比奴霉素类似物的治疗有效量，以降低Hsp-90客体蛋白CFTR、ErbB2、c-Raf和Cdk4的水平，或其组合。
• 一类含有生物活性基团的四价铂配合物及其 制备方法
  申请人：东南大学

  公开号：CN105622674B

  公开（公告）日：2018-02-02

  本发明是一类含有生物活性基团的四价铂配合物及其制备方法，所述的四价铂配合物即铂(IV)配合物，其结构如式II所示：式II中，Y为OH或Cl；Bio代表生物活性基团。所述的铂(IV)配合物，按照式III所示的反应式进行，式III中，Y为OH或Cl；Bio‑OH代表具有生物活性的化合物，TBTU代表偶联试剂O‑苯并三氮唑‑N，N，N′，N′‑四甲基脲四氟硼酸，TEA代表催化剂三乙胺，DMF代表溶剂N，N‑二甲基甲酰胺，DMSO代表溶剂二甲亚砜；采用顺铂为八面体底面，在一个轴向位置引入小分子靶向或药物活性基团，另一个轴向位置引入羟基或氯原子，提供具有克服顺铂耐药的抗肿瘤四价铂配合物，以期获得高效低毒的铂(IV)药物。
• A Mechanochemically Triggered “Click” Catalyst
  作者：Philipp Michael、Wolfgang H. Binder

  DOI：10.1002/anie.201505678

  日期：2015.11.16

  copper‐catalyzed “click” reaction (CuAAC) is achieved either by ultrasonication or mechanical pressing of a polymeric material, using a fluorogenic dye to detect the activation of the catalyst. Based on an N‐heterocyclic copper(I) carbene with attached polymeric chains of different flexibility, the force is transmitted to the central catalyst, thereby activating a CuAAC in solution and in the solid state.

  “点击”化学代表了化学和材料科学中连接分子的最强大方法之一。通过机械力触发此反应将启用特定于位置和应力的“喀哒”反应，这是迄今为止尚未报道的观察结果。我们介绍了均相Cu催化剂的设计和实现，该均相Cu催化剂在连接到合适的聚合物链上时能够通过机械力激活，充当将力传递到中央催化系统的杠杆。后续的铜催化的“喀哒”反应（CuAAC）的活化是通过超声或机械挤压聚合材料，使用荧光染料检测催化剂的活化来实现的。基于具有不同柔韧性的连接的聚合物链的N杂环铜（I）卡宾，力被传递至中心催化剂，
• A Fluorogenic 1,3-Dipolar Cycloaddition Reaction of 3-Azidocoumarins and Acetylenes
  作者：Krishnamoorthy Sivakumar、Fang Xie、Brandon M. Cash、Su Long、Hannah N. Barnhill、Qian Wang

  DOI：10.1021/ol047955x

  日期：2004.11.1

  Copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of nonfluorescent 3-azidocoumarins and terminal alkynes afforded intense fluorescent 1,2,3-triazole products. The mild condition of this reaction allowed us to construct a large library of pure fluorescent coumarin dyes. Since both azide and alkyne are quite inert to biological systems, this reaction has potential in bioconjugation and bioimaging

  铜（I）催化的非荧光3-azidocoumarins和末端炔烃的1,3-偶极环加成反应可提供强烈的荧光1,2,3-三唑产物。此反应的温和条件使我们能够构建一个大型的纯荧光香豆素染料库。由于叠氮化物和炔烃对生物系统都非常惰性，因此该反应在生物共轭和生物成像应用中具有潜力。[反应：看文字]
• Alkynyl–coumarinyl ethers as MAO-B inhibitors
  作者：Matthias D. Mertens、Sonja Hinz、Christa E. Müller、Michael Gütschow

  DOI：10.1016/j.bmc.2014.01.046

  日期：2014.3

  In this study, alkynyl–coumarinyl ethers were developed as inhibitors of human monoamine oxidase B (MAO-B). A series of 31 new, ether-connected coumarin derivatives was synthesized via hydroxycoumarins, whose phenolic group at position 6, 7 or 8 was converted by means of the Mitsunobu reaction. The majority of the final products were produced from primary alcohols with a terminal alkyne group. The

  在这项研究中，开发了炔基-香豆基醚作为人单胺氧化酶B（MAO-B）的抑制剂。通过羟基香豆素合成了31种新的，与醚连接的香豆素衍生物，该羟基香豆素的6、7或8位酚基通过Mitsunobu反应转化。大多数最终产品是由带有末端炔基的伯醇生产的。就炔基氧基链的结构及其在稠合苯环上的位置以及吡喃-2 H-一部分的3位上的残基而言，对抑制剂进行了优化。发现在位置7的六-5-炔氧基链是特别有利的。在7-己-5-炔氧基香豆素中，3-甲氧基羰基衍生物36被表征为具有IC的双作用抑制剂对MAO-A和MAO-B的50个值小于10 nM，并且3-（4-甲氧基）苯基衍生物44被证明具有强大的抗MAO-B效力（IC 50  = 3.0 nM）和对MAO的选择性-B高于MAO-A（选择性> 3400倍）。