2,3-dihydroxy-7,8,9,10-tetrahydro-6H-benzo[c]-chromen-6-one

• 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: 2,3-dihydroxy-7,8,9,10-tetrahydro-6H-benzo[c]-chromen-6-one
• 英文别名: 3,4-cyclohexenoesculetin；2,3-dihydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one；2,3-dihydroxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-one
• 化学式: C₁₃H₁₂O₄
• mdl: MFCD00488338
• 分子量: 232.236
• InChiKey: BYWQENRDUAFAAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxy-7,8,9,10-tetrahydro-6H-benzo[c]-chromen-6-one 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  A new visual screening assay for catalytic antibodies with retro-aldol retro-Michael activity

  摘要：

  Fast and convenient methods are required for the detection of novel catalysts. We have developed a new assay to allow direct visualization of retro-aldol retro-Michael catalytic activity and have demonstrated it with catalytic antibody 38C2. The assay is based on a catalytic cleavage of a physiologically stable substrate to release 3,4-cyclohexeneoesculetin. The latter then reacts with iron(III) to generate a non-soluble complex that precipitates in the form of a black dye. This assay may be used for screening new catalysts for retro-aldol retro-Michael activity with improved efficiency for specific prodrug activation.

  DOI：

  10.1016/j.bmcl.2006.12.057
• 作为产物：
  描述：

  7,8-di-O-(β-D-galactopyranosyl)-3,4-cyclohexenocoumarin 在 甲醇 、 氨 、 mercury(II) cyanide 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 乙腈 为溶剂， 生成 2,3-dihydroxy-7,8,9,10-tetrahydro-6H-benzo[c]-chromen-6-one
  参考文献：
  名称：

  基于 Fe3+ 的新型 1H MRI β-半乳糖苷酶报告分子

  摘要：

  人们对开发报告剂以利用小动物成像揭示体内酶活性越来越感兴趣。我们之前已经证明了使用市售的 3,4-环己烯七叶素-β- D-吡喃半乳糖苷 (S-Gal) 作为1 H MRI 报告基因检测lacZ基因活性的可行性。具体来说，β-半乳糖苷酶 (β-gal) 释放糖苷配基，在 Fe 3+存在的情况下形成磁共振对比诱导的顺磁性沉淀物。对比度主要是T 2加权信号损失，但也观察到T 1效应。由于T 1对比度通常提供信号增强而不是信号损失，因此探索是否可以生成具有增强特性的类似物似乎很有吸引力。我们现在报告新型类似物的设计和合成，以及基于T 1和T 2对先导药物体外 β-gal 活性的响应的1 H MRI 对比表征。

  DOI：

  10.1002/cplu.201100072

文献信息

• New Methods for the Synthesis of Spirocyclic Cephalosporin Analogues
  作者：Alan Zhao、Louise Horsfall、Alison Hulme

  DOI：10.3390/molecules26196035

  日期：——

  Spiro compounds provide attractive targets in drug discovery due to their inherent three-dimensional structures, which enhance protein interactions, aid solubility and facilitate molecular modelling. However, synthetic methodology for the spiro-functionalisation of important classes of penicillin and cephalosporin β-lactam antibiotics is comparatively limited. We report a novel method for the generation

  由于其固有的三维结构，螺环化合物在药物发现中提供了有吸引力的靶标，可增强蛋白质相互作用，有助于溶解度并促进分子建模。然而，重要类别青霉素和头孢菌素β-内酰胺抗生素的螺功能化的合成方法相对有限。我们报告了一种通过二氢噻嗪环的迈克尔型加成生成螺头孢菌素化合物的新方法。一系列儿茶酚的偶联是在弱碱性条件（K 2 CO 3 、DMF）下实现的，以中等至良好的产率（28−65%）立体选择性地形成螺头孢菌素（dr 14:1 至 8:1） 。
• Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins
  作者：James A. Bull、Cristina Luján、Michael G. Hutchings、Peter Quayle

  DOI：10.1016/j.tetlet.2009.03.077

  日期：2009.7

  A new approach to the synthesis of the 6H-benzo[d]naphthal[,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. (C) 2009 Elsevier Ltd. All rights reserved.
• Screening Broths Comprising Esculatin Compounds for the Detection of Specific Microorganisms
  申请人：Neogen Corporation

  公开号：US20180163250A1

  公开（公告）日：2018-06-14

  The present invention relates to the use of an esculatin compound in a method for detecting the presence or absence of an enzymatic reaction in a sample containing one or more enzymes and one or more first chromogenic indicator of one or more enzymatic reactions, wherein the esculatin compound is a compound of formula 1: or a suitable salt or hydrate thereof.
• PAPD5 INHIBITORS AND METHODS OF USE THEREOF
  申请人：Children`s Medical Center Corporation

  公开号：US20210177827A1

  公开（公告）日：2021-06-17

  The disclosure relates to compounds that are, e.g., PAP Associated Domain Containing 5 (PAPD5) inhibitors and methods of use thereof.
• US7531646B2
  申请人：——

  公开号：US7531646B2

  公开（公告）日：2009-05-12