2-(2-chlorophenoxy)propanoic acid methyl ester

• 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-chlorophenoxy)propanoic acid methyl ester
• 英文别名: methyl 2-(2-chlorophenoxy)propionate；methyl 2-(2-chlorophenoxy)propanoate
• 化学式: C₁₀H₁₁ClO₃
• mdl: MFCD04054697
• 分子量: 214.649
• InChiKey: FSLKEMBXNJKLCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenoxy)propanoic acid methyl ester 生成 (S)-methyl 2-(2-chlorophenoxy) propionate
  参考文献：
  名称：

  酯酶对2-（氯苯氧基）丙酸酯的对映选择性水解。

  摘要：

  发现α-胰凝乳蛋白酶，猪肝酯酶和猪胰或脂肪酶对外消旋2-（单，二和三氯苯氧基）-丙酸甲酯的酶促水解作用差到中等对映选择性。在大多数情况下，R酯优先水解。

  DOI：

  10.1016/s0040-4039(00)96590-0
• 作为产物：
  描述：

  2-(2-chloro-phenoxy)-propionyl chloride 生成 2-(2-chlorophenoxy)propanoic acid methyl ester
  参考文献：
  名称：

  酯酶对2-（氯苯氧基）丙酸酯的对映选择性水解。

  摘要：

  发现α-胰凝乳蛋白酶，猪肝酯酶和猪胰或脂肪酶对外消旋2-（单，二和三氯苯氧基）-丙酸甲酯的酶促水解作用差到中等对映选择性。在大多数情况下，R酯优先水解。

  DOI：

  10.1016/s0040-4039(00)96590-0

文献信息

• Synthesis and computer-aided SAR studies for derivatives of phenoxyalkyl-1,3,5-triazine as the new potent ligands for serotonin receptors 5-HT6
  作者：Wesam Ali、Małgorzata Więcek、Dorota Łażewska、Rafał Kurczab、Magdalena Jastrzębska-Więsek、Grzegorz Satała、Katarzyna Kucwaj-Brysz、Annamaria Lubelska、Monika Głuch-Lutwin、Barbara Mordyl、Agata Siwek、Muhammad Jawad Nasim、Anna Partyka、Sylwia Sudoł、Gniewomir Latacz、Anna Wesołowska、Katarzyna Kieć-Kononowicz、Jadwiga Handzlik

  DOI：10.1016/j.ejmech.2019.06.022

  日期：2019.9

  (Ki = 11 nM). SAR analysis indicated, that an exchange of oxygen to selenium (7 vs. 22), and especially, to sulfur (7 vs. 19) was beneficial to increase both affinity and antagonistic action for 5-HT6R. Surprisingly, an introduction of SO2 caused a drastic decrease of the 5-HT6R affinity, which was explained at a molecular level based on docking studies. All in vivo tested compounds (10, 18 and 21) did not

  这项研究提供了迄今为止所研究的1,3,5-三嗪衍生物中活性最高的5-HT 6 R药物，并且还确定了世界上第一个含硒的5-HT 6 R配体。这些研究主要针对新型5-HT 6 R试剂（作为铅结构4-（4-甲基哌嗪-1-基）-6-（苯氧甲基）-1）的衍生物进行设计，合成，生物学评估和对接支持的SAR分析， 3，5-三嗪-2-胺（7）。主要的修饰包括引入：（i）苯环上的各种小取代基，（ii）支化的醚连接基，或（iii）用其他硫族元素（S，Se）或磺酰基部分取代醚氧。因此，一系列新化合物（7 – 24）合成，并检查它们的亲和力对5-HT 6 R和选择性，对于5-HT 1A R，5-HT 2A R，5-HT 7 R和多巴胺d 2受体，在放射性配体结合测定。对于代表性的大多数活性化合物，进行了体外功能性生物测定和毒性分析，以及体内抗抑郁样活性。发现2-异丙基-5-甲基苯基衍生物（10）是活性最高的三嗪5-HT
• Enantioselective inhibition: strategy for improving the enantioselectivity of biocatalytic systems
  作者：Zhi Wei Guo、Charles J. Sih

  DOI：10.1021/ja00199a053

  日期：1989.8

  enantiomerically pure (R)-(+)-DCPP and (S)-(-)-DCPP. The observed inhibition pattern was that of partial noncompetitive inhibition for (R)-(+)-DCPP and that of pure noncompetitive inhibition for (S)-(-)-DCPP. Enantioselective biocatalysis in aqueous' and nonaqueousZ media is becoming increasingly important as a possible alternative method for the resolution of enantiomers. In recent years, hydrolytic enzymes such

  发现右美沙芬 (DM) 和左美沙芬 (LM) 是圆柱假丝酵母脂肪酶催化的多种 (*)-芳基丙酸酯和 (&)-(芳氧基)丙酸酯水解的有效对映选择性抑制剂。在 DM 或 LM 存在下，(&)-甲基 2-(2,4-二氯苯氧基)丙酸酯 (DCPP) 的生物催化拆分的对映选择性提高了 20 倍。已经开发了对映选择性抑制的通用模型，并且已经导出了定量表达式以显示控制对映选择性抑制的潜在参数。为了确定 DM 的作用机制，使用对映异构纯的 (R)-(+)-DCPP 和 (S)-(-)-DCPP 进行了一系列动力学抑制实验。观察到的抑制模式是 (R)-(+)-DCPP 的部分非竞争性抑制和 (S)-(-)-DCPP 的纯非竞争性抑制。水介质和非水介质中的对映选择性生物催化作为拆分对映体的一种可能的替代方法变得越来越重要。近年来，水解酶如猪肝酶、猪胰脂肪酶 Ic 和微生物脂肪酶 Ic (EC 3.1.1.3)
• Might the observed α2A-adrenoreceptor agonism or antagonism of allyphenyline analogues be ascribed to different molecular conformations?
  作者：Eleonora Diamanti、Fabio Del Bello、Giuseppe Carbonara、Antonio Carrieri、Giuseppe Fracchiolla、Mario Giannella、Valerio Mammoli、Alessandro Piergentili、Katariina Pohjanoksa、Wilma Quaglia、Mika Scheinin、Maria Pigini

  DOI：10.1016/j.bmc.2012.01.035

  日期：2012.3

  We recently reported that the alpha(2)-adrenoreceptor (AR) ligand allyphenyline (9) significantly enhanced morphine analgesia (due to its alpha(2C)-AR agonism), was devoid of sedative side effects (due to its alpha(2A)-AR antagonism), prevented and reversed morphine tolerance and dependence. To highlight the molecular characteristics compatible with this behaviour and to obtain novel agents potentially useful in chronic pain and opioid addiction management, the allyl group of 9 was replaced by substituents of moderate steric bulk (MR) and positive or negative lipophilic (pi) and electronic (sigma) contributions in all the possible combinations. Effective novel alpha(2C)-agonists/alpha(2A)-antagonists (2, 3, 10, 12, and 17) were obtained. This study also demonstrated that contradictory combinations of the physicochemical parameters were similarly able to induce the alpha(2A)-activation. Since we had previously observed that the absolute configuration affected only the potency, but not the functional profile of the ligands, we hypothesized that the alpha(2A)-activation was governed by a ligand preferred conformation. From a structural overlay investigation it emerged that an extended conformation appeared to be associated with dual alpha(2C)-agonism/alpha(2A)-antagonism, whereas a folded conformation associated with alpha(2C)-/alpha(2A)-agonism. (C) 2012 Elsevier Ltd. All rights reserved.
• A new biocatalyst for the preparation of enantiomerically pure 2-arylpropanoic acids
  作者：Ish Kumar、Kavita Manju、Ravinder S. Jolly

  DOI：10.1016/s0957-4166(01)00249-x

  日期：2001.6

  A new biocatalyst. a strain of Pseudomonas fluorescens MTCCB0015. is described. which produces ibuprofen. ketoprofen and flurbiprofen as enantiomerically pure (S)-2-arylpropanoic acids from their corresponding racemic esters. 2-Arylpropanoic acids are an important class of non-steroidal anti-inflammatory, compound,. whose anti-inflammatory activity is mainly due to the (S)-enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Azzolina; Collina; Ghislandi, Il Farmaco, 1993, vol. 48, # 10, p. 1401 - 1416
  作者：Azzolina、Collina、Ghislandi

  DOI：——

  日期：——