5-tert-Butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester | 863483-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-tert-Butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester
• CAS: 863483-01-6
• 化学式: C₂₀H₂₆INO₇
• 分子量: 519.333
• InChiKey: FHYJPAMHBUNZGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-tert-Butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl ester 在 palladium on activated charcoal 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 乙酸铵 、 copper(l) iodide 、 氢气 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 xylene 为溶剂， 反应 30.0h， 生成 {2,2-Dimethyl-5-[5-(4-octyl-phenyl)-1H-imidazol-2-yl]-[1,3]dioxan-5-yl}-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
• 作为产物：
  描述：

  (5-甲酰基-2,2-二甲基-1,3-二氧六环-5-基)氨基甲酸叔丁酯 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 caesium carbonate 作用下， 以 乙醇 、 叔丁醇 为溶剂， 反应 3.0h， 生成 5-tert-Butoxycarbonylamino-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid 2-(4-iodo-phenyl)-2-oxo-ethyl 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