2-(4-(2-chlorobenzyloxy)phenyl)ethanol | 1228930-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-(2-chlorobenzyloxy)phenyl)ethanol
• 英文别名: 2-[4-[(2-Chlorophenyl)methoxy]phenyl]ethanol
• CAS: 1228930-61-7
• 化学式: C₁₅H₁₅ClO₂
• mdl: MFCD15523482
• 分子量: 262.736
• InChiKey: VORXTVKVVWITTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-(2-chlorobenzyloxy)phenyl)ethanol 在 2,2,6,6-四甲基哌啶氧化物 、 sodium bromite trihydrate 、 碳酸氢钠 、 sulfur 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 2-(4-chlorobenzamido)-5-(4-(2-chlorobenzyloxy)phenyl)thiophene-3-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1

  摘要：

  A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb) growth with MIC values between 1.9 and 7.7 mu M and low toxicity against VERO cells. The four compounds were also tested against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) clinical strains, which were found to show moderate activity. In addition, molecular docking simulation was performed to position compounds 10d, 15, 12h and 12k into mtFabH active site to predict the probable binding mode. These studies thus suggest that the designed 2-amino-5-phenylthiophene-3-carboxylic acid scaffold may serve as new promising template for further elaboration as anti-TB drugs. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.018
• 作为产物：
  描述：

  对羟基苯乙醇 、 邻氯氯苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以100%的产率得到2-(4-(2-chlorobenzyloxy)phenyl)ethanol
  参考文献：
  名称：

  Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1

  摘要：

  A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb) growth with MIC values between 1.9 and 7.7 mu M and low toxicity against VERO cells. The four compounds were also tested against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) clinical strains, which were found to show moderate activity. In addition, molecular docking simulation was performed to position compounds 10d, 15, 12h and 12k into mtFabH active site to predict the probable binding mode. These studies thus suggest that the designed 2-amino-5-phenylthiophene-3-carboxylic acid scaffold may serve as new promising template for further elaboration as anti-TB drugs. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.018

文献信息

• Novel immunomodulators based on an oxazolin-2-one-4-carboxamide scaffold
  作者：Xinhua He、Lili Wang、Zhibing Zheng、Junhai Xiao、Wu Zhong、Song Li

  DOI：10.1016/j.bmcl.2011.10.088

  日期：2012.1

  A series of oxazolidin-2-one-4-carboxylic amide compounds (1a-f) were designed and synthesized as the non-phosphate S1P1 receptor agonists. The single crystal of 1e was prepared and solved to elucidate the structure of 1a-f. EC(50) of 1a-d were about 1.1-3.6 mu M in S1P(1) Redistribution (R) assay, and their cytotoxicity was 8-40-fold lower than FTY720. Though its S1P(1) agonist activities in vitro were about 1000-folds weaker than (S)-FTY720-P, at a dose of 10 mg/Kg, the immunosuppressive effects of 1a were comparable to FTY720. So oxazolidin-2-one-4-carboxylic amide derivatives were found as potential immunomodulator, compound 1a could be considered as a lead compound, rational modifications of 1a are anticipated using medicinal chemistry techniques and molecular modeling to obtain analogs with higher affinity and better clinical therapeutic properties. (C) 2011 Elsevier Ltd. All rights reserved.
• Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1
  作者：Xiaoyun Lu、Baojie Wan、Scott G. Franzblau、Qidong You

  DOI：10.1016/j.ejmech.2011.05.018

  日期：2011.9

  A series of 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives were synthesized and evaluated for anti-tubercular activity. Among these compounds, 10d, 15, 12h and 12k inhibited Mycobacterium tuberculosis (Mtb) growth with MIC values between 1.9 and 7.7 mu M and low toxicity against VERO cells. The four compounds were also tested against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) clinical strains, which were found to show moderate activity. In addition, molecular docking simulation was performed to position compounds 10d, 15, 12h and 12k into mtFabH active site to predict the probable binding mode. These studies thus suggest that the designed 2-amino-5-phenylthiophene-3-carboxylic acid scaffold may serve as new promising template for further elaboration as anti-TB drugs. (C) 2011 Elsevier Masson SAS. All rights reserved.