2-(2-oxo-2-propoxyethyl)benzoic acid | 1034706-09-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-oxo-2-propoxyethyl)benzoic acid
• CAS: 1034706-09-6
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: QUSQKRKIILDMGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-oxo-2-propoxyethyl)benzoic acid 在 五氯化磷 作用下， 以 甲苯 为溶剂， 生成 3-propoxy-4-chloroisocoumarin
  参考文献：
  名称：

  4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents

  摘要：

  4-Chloroisocoumarin compounds have broad inhibitory properties against serine proteases. Here, we show that selected 3-alkoxy-4-chloroisocoumarins preferentially inhibit the activity of the conserved serine protease High-temperature requirement A of Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based scaffolds has been developed, and their anti-chlamydial properties were investigated. The structure of the alkoxy substituent was found to influence the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure attenuate anti-chlamydial properties.

  DOI：

  10.3390/molecules29071519
• 作为产物：
  描述：

  丙醇 、 邻羧基苯乙酸 在 硫酸 作用下， 生成 2-(2-oxo-2-propoxyethyl)benzoic acid
  参考文献：
  名称：

  4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents

  摘要：

  4-Chloroisocoumarin compounds have broad inhibitory properties against serine proteases. Here, we show that selected 3-alkoxy-4-chloroisocoumarins preferentially inhibit the activity of the conserved serine protease High-temperature requirement A of Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based scaffolds has been developed, and their anti-chlamydial properties were investigated. The structure of the alkoxy substituent was found to influence the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure attenuate anti-chlamydial properties.

  DOI：

  10.3390/molecules29071519

文献信息

• Diesters cycliques et leur utilisation à titre d'ingrédients parfumants
  申请人：FIRMENICH SA

  公开号：EP0694605A2

  公开（公告）日：1996-01-31

  Composition parfumante ou article parfumé contenant à titre d'ingrédient parfumant un composé de formule dans laquelle le groupe Z peut se trouver dans des positions ortho-, meta- ou para- par rapport au groupe carboxylique, le symbole R¹ représente un radical alkyle saturé ou insaturé, linéaire ou ramifié, ayant de 1 à 4 atomes de carbone et a. les lignes pointillées représentent un noyau cyclohexanique et Z représente un groupe R² représentant un radical alkyle saturé ou insaturé, linéaire ou ramifié, ayant de 1 à 4 atomes de carbone ; ou b. les lignes pointillées représentent un noyau cyclohexanique ou benzénique, et Z représente un groupe de formule dans laquelle R² a le sens indiqué ci-dessus.

  香水组合物或香水制品，含有作为香水成分的式化合物 其中基团 Z 相对于羧基可处于正位、偏位或对位，符号 R¹ 代表具有 1 至 4 个碳原子的饱和或不饱和、直链或支链烷基，以及 a. 虚线代表环己烷环，Z 代表一个基团 R² 代表具有 1 至 4 个碳原子的饱和或不饱和、直链或支链烷基； 或 b. 虚线代表环己烷或苯环，Z 代表一个式中的基团 其中 R² 具有上述含义。
• Isocoumarin-based inhibitors of pancreatic cholesterol esterase
  作者：Justin J. Heynekamp、Lucy A. Hunsaker、Thomas A. Vander Jagt、Robert E. Royer、Lorraine M. Deck、David L. Vander Jagt

  DOI：10.1016/j.bmc.2008.03.016

  日期：2008.5

  Pancreatic cholesterol esterase (CEase), which is secreted from the exocrine pancreas, is a serine hydrolase that aids in the bile salt-dependent hydrolysis of dietary cholesteryl esters and contributes to the hydrolysis of triglycerides and phospholipids. Additional roles for CEase in intestinal micelle formation and in transport of free cholesterol to the enterocyte have been suggested. There also are studies that point to a pathological role(s) for CEase in the circulation where CEase accumulates in atherosclerotic lesions and triggers proliferation of smooth muscle cells. Thus, there is interest in CEase as a potential drug target. 4-Chloro-3-alkoxyisocoumarins are a class of haloenol lactones that inhibit serine hydrolases and serine proteases and have the potential to be suicide inhibitors. In the present study, we have developed 3-alkoxychloroisocoumarins that are potent inhibitors of CEase. These inhibitors were designed to have a saturated cycloalkane ring incorporated into a 3-alkoxy substituent. The size of the ring as well as the length of the tether holding the ring was found to be important contributors to binding to CEase. 4-Chloro-3-(4-cyclohexylbutoxy) isocoumarin and 4-chloro-3-(3-cyclopentylpropoxy) isocoumarin were demonstrated to be potent reversible inhibitors of CEase, with dissociation constants of 11 nM and 19 nM, respectively. The kinetic results are consistent with predictions from molecular modeling. (C) 2008 Elsevier Ltd. All rights reserved.
• 4-Chloroisocoumarins as Chlamydial Protease Inhibitors and Anti-Chlamydial Agents
  作者：Matthew J. A. Phillips、Wilhelmina M. Huston、Andrew M. McDonagh、Tristan Rawling

  DOI：10.3390/molecules29071519

  日期：——

  4-Chloroisocoumarin compounds have broad inhibitory properties against serine proteases. Here, we show that selected 3-alkoxy-4-chloroisocoumarins preferentially inhibit the activity of the conserved serine protease High-temperature requirement A of Chlamydia trachomatis. The synthesis of a new series of isocoumarin-based scaffolds has been developed, and their anti-chlamydial properties were investigated. The structure of the alkoxy substituent was found to influence the potency of the compounds against High-temperature requirement A, and modifications to the C-7 position of the 3-alkoxy-4-chloroisocoumarin structure attenuate anti-chlamydial properties.