7-羟基-2-氧代-2H-1-苯并吡喃-4-羧酸乙酯 | 1084-45-3

• 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: 7-羟基-2-氧代-2H-1-苯并吡喃-4-羧酸乙酯
• 中文别名: 乙基-7-羟基香豆素-4-羧酸；7-羟基香豆素-4-羧酸乙酯
• 英文名称: ethyl 7-hydroxy-2-oxo-2H-chromene-4-carboxylate
• 英文别名: Ethyl 7-hydroxycoumarin-4-carboxylate；ethyl 7-hydroxy-2-oxochromene-4-carboxylate
• CAS: 1084-45-3
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: SNMUERBNQDOIQB-UHFFFAOYSA-N

物化性质

• 熔点：
  149-151
• 沸点：
  448.3±45.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  7-羟基-2-氧代-2H-1-苯并吡喃-4-羧酸乙酯 在 sodium hydroxide 作用下， 生成 7-Hydroxy-4-coumarinylacetic acid
  参考文献：
  名称：

  In situ fluorescence imaging reveals that mitochondrial H₂O₂ mediates lysosomal dysfunction in depression

  摘要：

  我们使用了两种新型荧光探针，以识别从氧化应激下线粒体H₂O₂积累开始的时间依赖性病理级联反应，导致升高的溶酶体H₂O₂，最终导致抑郁小鼠大脑中GCase酶活性降低的结果。

  DOI：

  10.1039/d2cc00431c
• 作为产物：
  描述：

  Ethyl 2-oxo-7-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methoxy]chromene-3-carboxylate 在 双氧水 作用下， 以 aq. buffer 为溶剂， 生成 7-羟基-2-氧代-2H-1-苯并吡喃-4-羧酸乙酯
  参考文献：
  名称：

  双响应荧光探针可通过胱硫醚β-合酶途径揭示H2O2诱导的H2S生物发生。

  摘要：

  两个信号分子H 2 S和H 2 O 2在维持细胞内氧化还原稳态中起着关键作用。H 2 O 2和H 2 S之间的生物学关系在氧化还原生物学中仍然是未知的。在这项研究中，我们合理地设计和合成了用于检测活细胞中H 2 O 2和H 2 S的单响应和双响应荧光探针。双重反应探针显示出能够对H 2 O 2和H 2进行单次和双重检测S有选择地和敏感地。基于探针的详细生物成像研究表明，外源性和内源性H 2 O 2均可诱导活细胞中H 2 S生物发生。通过对生物成像使用基因敲低技术，发现H 2 S生物发生主要依赖于胱硫醚β-合酶（CBS）。我们的发现显示了体内H 2 O 2（ROS）和H 2 S（RSS）之间的生物通讯的第一个直接证据。

  DOI：

  10.1002/chem.201502832

文献信息

• Discovery, Biological Evaluation, and Structure–Activity and −Selectivity Relationships of 6′-Substituted (<i>E</i>)-2-(Benzofuran-3(2<i>H</i>)-ylidene)-<i>N</i>-methylacetamides, a Novel Class of Potent and Selective Monoamine Oxidase Inhibitors
  作者：Leonardo Pisani、Maria Barletta、Ramon Soto-Otero、Orazio Nicolotti、Estefania Mendez-Alvarez、Marco Catto、Antonellina Introcaso、Angela Stefanachi、Saverio Cellamare、Cosimo Altomare、Angelo Carotti

  DOI：10.1021/jm4000769

  日期：2013.3.28

  The use of selective inhibitors of monoamine oxidase A (MAO-A) and B (MAO-B) holds a therapeutic relevance in the treatment of depressive disorders and Parkinson’s disease (PD), respectively. Here, the discovery of a new class of compounds acting as monoamine oxidase inhibitors (MAO-Is) and bearing a 6′-substituted (E)-2-(benzofuran-3(2H)-ylidene)-N-alkylacetamide skeleton is reported. 6′-Sulfonyloxy

  使用单胺氧化酶A（MAO-A）和B（MAO-B）的选择性抑制剂分别在抑郁症和帕金森氏病（PD）的治疗中具有治疗意义。在这里，发现了一类新的充当单胺氧化酶抑制剂（MAO-Is）并带有6'-取代的（E）-2-（苯并呋喃-3（2 H）-亚烷基）-N-烷基乙酰胺骨架的化合物报告。6'-磺酰氧基衍生物表现出对MAO-A的出色亲和力（7.0 nM
• Ethers of 7-hydroxy-coumarin useful as medicaments
  申请人：Unicler

  公开号：US04151291A1

  公开（公告）日：1979-04-24

  The invention provides novel esters of 7-hydroxycoumarin of the formula ##STR1## in which each of R.sub.1 and R.sub.2 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, carboxy, carboxylate, C.sub.2 -C.sub.5 alkoxycarbonyl or nitrophenyl group, and R.sub.3 represents a hydrogen atom or a group of the formula --CH.sub.2 --Z in which Z represents a di(C.sub.1 -C.sub.4 alkyl)amino group, or a saturated heterocyclic amino radical containing 5 to 7 ring members which may contain a further heteroatom, and their pharmaceutically acceptable acid addition salts. The compounds are useful as medicaments, in particular as analgesics.

  该发明提供了新型7-羟基香豆素的酯类化合物，其化学式为##STR1##其中R.sub.1和R.sub.2分别代表氢原子，C.sub.1 -C.sub.4烷基，C.sub.2 -C.sub.4烯基，羧基，羧酸酯，C.sub.2 -C.sub.5烷氧羰基或硝基苯基；R.sub.3代表氢原子或具有--CH.sub.2 --Z的基团，其中Z代表二(C.sub.1 -C.sub.4烷基)氨基基团，或含有5到7个环成员的饱和杂环氨基基团，其中可能含有进一步的杂原子，以及它们的药用可接受的酸盐。这些化合物可用作药物，特别是作为镇痛药。
• Farnesoid X Receptor Agonists
  申请人：Deaton David Norman

  公开号：US20100249179A1

  公开（公告）日：2010-09-30

  The present invention provides novel isoxazole compounds, pharmaceutical compositions, therapeutic uses and processes for preparing the same.

  本发明提供了新型异噁唑化合物、制药组合物、治疗用途和制备方法。
• Fine molecular tuning at position 4 of 2H-chromen-2-one derivatives in the search of potent and selective monoamine oxidase B inhibitors
  作者：Leonardo Pisani、Marco Catto、Orazio Nicolotti、Giancarlo Grossi、Mario Di Braccio、Ramon Soto-Otero、Estefania Mendez-Alvarez、Angela Stefanachi、Domenico Gadaleta、Angelo Carotti

  DOI：10.1016/j.ejmech.2013.09.034

  日期：2013.12

  The effects on the inhibition potencies of monoamine oxidase isoforms A (MAO-A) and B (MAO-B) depending upon changes in the physicochemical properties (size, shape, H-bonding, lipophilicity, etc.) of substituents at the C4 position of 2H-chromen-2-one derivatives were extensively investigated, and the results significantly added to our knowledge on this class of MAO inhibitors. All the 67 examined compounds showed high MAO-B selectivity, some of them achieving potency in the low nanomolar range. In particular, the 7-metachlorobenzyloxy-4-oxyacetamido-211-chromen-2-one (entry 62) showed single digit nanomolar MAO-B potency (IC50 = 3.1 nM) and high selectivity over the MAO-A isoform (selectivity ratio = 7244). The great variety of the investigated substituents at C4 of the 2H-chromen-2-one nucleus, combined with binding models generated from docking studies carried out on selected compounds, allowed us to shed light on the main molecular requirements for potent and selective MAO-B inhibition, highlighting the dominant role of the steric effects. Interestingly, many of the designed substituents could be metabolically related to each other (e.g., CH3/CH2OH/CHO/COOH; NH2/NHCH3, NHAc), and therefore the results obtained may help in predicting the in vivo activity of some putative metabolites of lead MAO-B inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Coumarins. I. Derivatives of Coumarin-3- and 4-Carboxylic Acids
  作者：R. O. Clinton、S. C. Laskowski

  DOI：10.1021/ja01179a007

  日期：1949.11.19