4-[2-[4-[(2-Chlorophenyl)methoxy]phenyl]ethyl]-2-oxo-1,3-oxazolidine-4-carboxamide | 1228930-51-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[2-[4-[(2-Chlorophenyl)methoxy]phenyl]ethyl]-2-oxo-1,3-oxazolidine-4-carboxamide
• CAS: 1228930-51-5
• 化学式: C₁₉H₁₉ClN₂O₄
• 分子量: 374.824
• InChiKey: VIXIHNMGNDQBFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-((tert-butoxycarbonyl)amino)-4-(4-((2-chlorobenzyl)oxy)phenyl)-2-cyanobutanoate 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-[2-[4-[(2-Chlorophenyl)methoxy]phenyl]ethyl]-2-oxo-1,3-oxazolidine-4-carboxamide
  参考文献：
  名称：

  Novel immunomodulators based on an oxazolin-2-one-4-carboxamide scaffold

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.10.088

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.