tert-butyl N-[1-hydroxy-4-(4-octylphenyl)butan-2-yl]carbamate | 596820-24-5

• 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: tert-butyl N-[1-hydroxy-4-(4-octylphenyl)butan-2-yl]carbamate
• CAS: 596820-24-5
• 化学式: C₂₃H₃₉NO₃
• 分子量: 377.568
• InChiKey: CVISKDFOMDAORA-UHFFFAOYSA-N

物化性质

• 沸点：
  519.4±50.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[1-hydroxy-4-(4-octylphenyl)butan-2-yl]carbamate 在 四氮唑 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.0h， 生成 [1-(Di-tert-butoxy-phosphoryloxymethyl)-3-(4-octyl-phenyl)-propyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

  摘要：

  Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1 -phosphate (SIP) G-protein coupled receptors. Unlike their phosphate precursors, phosphothioate compounds with SIP-receptor profiles similar to that of FTY720, an emerging immunomodulator, were shown to evoke prolonged lymphopenia in vivo. Analysis of mouse plasma concentrations for a series of related alcohol/phosphate/phosphothioate compounds showed the conversion of the phosphate to alcohol. These preliminary data highlight the importance of metabolic regulation of SIP receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.057
• 作为产物：
  描述：

  1-苯基辛烷 在 盐酸 、 三乙基硅烷 、 三氯化铝 、 sodium ethanolate 、 四氯化钛 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 tert-butyl N-[1-hydroxy-4-(4-octylphenyl)butan-2-yl]carbamate
  参考文献：
  名称：

  Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

  摘要：

  Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1 -phosphate (SIP) G-protein coupled receptors. Unlike their phosphate precursors, phosphothioate compounds with SIP-receptor profiles similar to that of FTY720, an emerging immunomodulator, were shown to evoke prolonged lymphopenia in vivo. Analysis of mouse plasma concentrations for a series of related alcohol/phosphate/phosphothioate compounds showed the conversion of the phosphate to alcohol. These preliminary data highlight the importance of metabolic regulation of SIP receptor ligands. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.057

文献信息

• Potent S1P receptor agonists replicate the pharmacologic actions of the novel immune modulator FTY720
  作者：Jeffrey J. Hale、William Neway、Sander G. Mills、Richard Hajdu、Carol Ann Keohane、Mark Rosenbach、James Milligan、Gan-Ju Shei、Gary Chrebet、James Bergstrom、Deborah Card、Gloria C. Koo、Sam L. Koprak、Jesse J. Jackson、Hugh Rosen、Suzanne Mandala

  DOI：10.1016/j.bmcl.2004.02.106

  日期：2004.6

  corresponding phosphate ester 2 can be induced by the systemic administration of potent sphingosine-1-phosphate receptor agonists exemplified by 19. The similar S1P receptor profiles of 2 and 19 coupled with their comparable potency in vivo supports a connection between S1P receptor agonism and immunosuppressive efficacy.

  暴露于FTY720（1）或其相应的磷酸酯2后观察到的啮齿动物淋巴细胞运输的改变和移植物排斥的阻止可通过全身性施用有效的鞘氨醇-1-磷酸受体激动剂（例如19）来诱导。相似的S1P受体概况2和19中的1结合其在体内的可比性，支持了S1P受体激动作用与免疫抑制功效之间的联系。
• Aminoalkylphosphonates and related compounds as edg receptor agonists
  申请人：Budhu J Richard

  公开号：US20060089334A1

  公开（公告）日：2006-04-27

  The present invention encompasses compounds or Formula (I): as well as the pharmaceutically acceptable salts and hydrates thereof. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.

  本发明涵盖化合物或式（I）及其药学上可接受的盐和水合物。这些化合物可用于治疗免疫介导的疾病和病状，例如骨髓、器官和组织移植排斥。还包括药物组合物和使用方法。
• Aminoalkylphosphonates and related compounds as Edg receptor agonists
  申请人：Doherty A. George

  公开号：US20070224263A1

  公开（公告）日：2007-09-27

  The present invention encompasses compounds of Formula II: as well as the pharmaceutically acceptable salts and hydrates thereof. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.

  本发明涵盖了II式化合物，以及其医药上可接受的盐和水合物。这些化合物可用于治疗免疫介导的疾病和病状，例如骨髓、器官和组织移植排斥。还包括药物组成物和使用方法。
• EP1482895A4
  申请人：——

  公开号：EP1482895A4

  公开（公告）日：2005-04-27
• AMINOALKYLPHOSPHONATES AND RELATED COMPOUNDS AS EDG RECEPTOR AGONISTS
  申请人：Merck & Co., Inc.

  公开号：EP1482895A2

  公开（公告）日：2004-12-08