7-Benzoyloxycoumarin | 31005-05-7

• 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: 7-Benzoyloxycoumarin
• 英文别名: 7-(phenylcarbonyl)oxy-2H-1-benzopyran-2-one；2-oxo-2H-chromen-7-yl benzoate；7-Benzoyloxy-cumarin；Benzoic acid 2-oxo-2H-chromen-7-yl ester；(2-oxochromen-7-yl) benzoate
• CAS: 31005-05-7
• 化学式: C₁₆H₁₀O₄
• mdl: MFCD01107157
• 分子量: 266.253
• InChiKey: DKDPSSSGXHEHAK-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C
• 沸点：
  454.0±40.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-Benzoyloxycoumarin 在 三氯化铝 、 溴 、 溶剂黄146 作用下， 生成 8-benzoyl-3-bromo-7-hydroxy-coumarin
  参考文献：
  名称：

  Marathey; Athavale, Journal of the University of Poona, Science and Technology, 1953, # 4, p. 90,92

  摘要：

  DOI：
• 作为产物：
  描述：

  7-甲氧基香豆素 、 苯甲酰氯 在 hexabutylguanidium chloride hydrochloride 作用下， 以 邻二氯苯 为溶剂， 反应 0.67h， 以75%的产率得到7-Benzoyloxycoumarin
  参考文献：
  名称：

  A simple and efficient transprotection of aryl methyl ether to aryl benzoate under microwave activation

  摘要：

  A simple and efficient method for the transprotection of aryl methyl ether to easily cleavable arylbenzoate mediated by microwave activation has been developed. One important feature of this method is its high tolerance towards sensitive functionalities and to some extent to bulky environment. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.124

文献信息

• Highly Active Manganese-Mediated Acylation of Alcohols with Acid Chlorides or Anhydrides
  作者：Seung-Hoi Kim、Seong-Ryu Joo、Young-Jin Youn、Young-Ran Hwang

  DOI：10.1055/s-0036-1590973

  日期：2017.12

  To explore further the practical uses of highly active manganese (Mn*), a variety of alcohols were treated with Mn*, and the resulting complexes were coupled with acid chlorides and/or acetic anhydride in the absence of any extra catalyst. The subsequent reactions took place smoothly under mild conditions, providing the corresponding O-acylation products in good to excellent isolated yields.

  为了进一步探索高活性锰 (Mn*) 的实际用途，用 Mn* 处理各种醇，在没有任何额外催化剂的情况下，将所得配合物与酰氯和/或乙酸酐偶联。随后的反应在温和的条件下顺利进行，提供了相应的 O-酰化产物，分离产率良好至极好。
• A High-Throughput, Low-Volume Enzyme Assay on Solid Support
  作者：Peter Babiak、Jean-Louis Reymond

  DOI：10.1021/ac048611n

  日期：2005.1.1

  water-soluble substrates (glycosidases), whole-protein substrates (proteases), and enzyme inhibition measurements. Hydrolytically labile umbelliferyl esters can be used to assay lipases in this format without background hydrolysis. High throughput and reproducibility were tested by fingerprint analysis of lipases and esterases against 37 different fluorogenic ester substrates. A set of eight fluorogenic unbelliferyl

  描述了一种高通量酶测定法，该测定法每次测试使用1微升或更少的酶溶液。酶溶液通过机器人处理以超过1000次/小时的处理量沉积在已预浸渍有荧光底物的硅胶板表面上。通过荧光定量反应。该方法与水不溶性底物（脂肪酶），水溶性底物（糖苷酶），全蛋白底物（蛋白酶）和酶抑制测量兼容。水解不稳定的伞形酯可用于以这种形式测定脂肪酶，而无需进行背景水解。通过对37种不同的荧光酯底物进行脂肪酶和酯酶的指纹分析，测试了高通量和可重复性。
• Inhibitory effects and structural insights for a novel series of coumarin-based compounds that selectively target human CA IX and CA XII carbonic anhydrases
  作者：Laura De Luca、Francesca Mancuso、Stefania Ferro、Maria Rosa Buemi、Andrea Angeli、Sonia Del Prete、Clemente Capasso、Claudiu T. Supuran、Rosaria Gitto

  DOI：10.1016/j.ejmech.2017.11.061

  日期：2018.1

  class of inhibitors of the family of metalloenzymes carbonic anhydrases (CA, EC 4.2.1.1). Several coumarins display higher affinity and selectivity toward most relevant and druggable CA isoforms. By decorating the natural compound umbelliferone (1) we have identified a new series of coumarin-based compounds demonstrating high CA inhibitory effects with nanomolar affinity for hCA IX and hCA XII isoforms

  香豆素衍生物是金属酶碳酸酐酶家族的一种特殊抑制剂（CA，EC 4.2.1.1）。几种香豆素对最相关且可药物处理的CA同工型显示出更高的亲和力和选择性。通过装饰天然化合物伞形酮（1），我们确定了一系列新的基于香豆素的化合物，它们对hCA IX和hCA XII亚型具有纳摩尔摩尔亲和力，显示出高的CA抑制作用，被认为是可开发抗肿瘤药物的靶标。经测试，活性最高的化合物是K i的有效抑制剂。其值等于众所周知的抑制剂乙酰唑胺（AAZ）的值，后者对普遍存在的hCA I和hCA II缺乏选择性。正如对接研究所建议的那样，缺少经典金属结合基团的香豆素在催化位点内不与锌离子相互作用，这是经典的磺酰胺类CAs所发现的。因此，所研究的抑制剂可能具有非经典的抑制作用方式，可阻止二氧化碳进入催化腔并阻止其转化为碳酸氢根离子。特别是，hCA XII化合物18i（K i值为5.5 nM）最具活性的抑制剂及其假定的水解产物可以在酶腔内建立H键相互作用网。
• Specific substrate of an ALDH isoenzyme
  申请人：ADVANCED BIODESIGN

  公开号：US11519014B2

  公开（公告）日：2022-12-06

  The invention relates to a specific substrate on an ALDH isoenzyme, to a composition comprising at least one such substrate, to a diagnostic marker comprising such a substrate, and to the uses thereof and associated methods.

  本发明涉及一种 ALDH 同工酶上的特异性底物，涉及一种包含至少一种此类底物的组合物，涉及一种包含此类底物的诊断标记物，还涉及其用途和相关方法。
• Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs
  作者：Amanda Sánchez-Recillas、Gabriel Navarrete-Vázquez、Sergio Hidalgo-Figueroa、María Yolanda Rios、Maximiliano Ibarra-Barajas、Samuel Estrada-Soto

  DOI：10.1016/j.ejmech.2014.03.029

  日期：2014.4

  Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (E-max = 100%), where compound 2 (42 mu M) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP. (C) 2014 Elsevier Masson SAS. All rights reserved.