{(S)-2-(Di-tert-butoxy-phosphoryloxy)-1-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-ethyl}-carbamic acid tert-butyl ester | 863482-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: {(S)-2-(Di-tert-butoxy-phosphoryloxy)-1-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-ethyl}-carbamic acid tert-butyl ester
• CAS: 863482-79-5
• 化学式: C₃₂H₅₄N₃O₆P
• 分子量: 607.771
• InChiKey: ZKFPXFVNQWDGJZ-HHHXNRCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  111.77
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  {(S)-2-(Di-tert-butoxy-phosphoryloxy)-1-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-ethyl}-carbamic acid tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 4.0h， 以100%的产率得到Phosphoric acid mono-{(S)-2-amino-2-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-ethyl} ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Synthesis of 4(5)-phenylimidazole-based analogues of sphingosine-1-phosphate and FTY720: Discovery of potent S1P1 receptor agonists

  摘要：

  The novel immunosuppressant FTY720 has been demonstrated to elicit immunomodulating effects via interaction with the G-protein coupled receptor S1P(1). FTY720 induced agonism at the S1P(3) receptor, however, has been shown to result in mild bradycardia, a minor side-effect of initial FTY720 therapy. This report describes the synthesis of several potent 4(5)-phenylimidazole-based SIP, receptor agonists that are accompanied by poor agonist activity at S1P(3). For instance, compound 20 displayed an EC50 = 4.7 +/- 1.3 nM at the S1P(1), receptor and EC50 = 780 +/- 1.3 nM at the SIP3 receptor using a [gamma-S-35]GTP-binding assay as compared to phospho-FTY720 (S1P(1): EC50 = 1.3 +/- 1.3 nM, S1P(3): EC50 = 2.0 +/- 2.4 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.097
• 作为产物：
  描述：

  {(S)-2-Benzyloxy-1-[5-(4-oct-1-ynyl-phenyl)-1H-imidazol-2-yl]-ethyl}-carbamic acid tert-butyl ester 在 四氮唑 、 氨 、 双氧水 、 sodium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.08h， 生成 {(S)-2-(Di-tert-butoxy-phosphoryloxy)-1-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 4(5)-phenylimidazole-based analogues of sphingosine-1-phosphate and FTY720: Discovery of potent S1P1 receptor agonists

  摘要：

  The novel immunosuppressant FTY720 has been demonstrated to elicit immunomodulating effects via interaction with the G-protein coupled receptor S1P(1). FTY720 induced agonism at the S1P(3) receptor, however, has been shown to result in mild bradycardia, a minor side-effect of initial FTY720 therapy. This report describes the synthesis of several potent 4(5)-phenylimidazole-based SIP, receptor agonists that are accompanied by poor agonist activity at S1P(3). For instance, compound 20 displayed an EC50 = 4.7 +/- 1.3 nM at the S1P(1), receptor and EC50 = 780 +/- 1.3 nM at the SIP3 receptor using a [gamma-S-35]GTP-binding assay as compared to phospho-FTY720 (S1P(1): EC50 = 1.3 +/- 1.3 nM, S1P(3): EC50 = 2.0 +/- 2.4 nM). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.097