tert-butyl (S)-2-(4-(octyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate | 876913-65-4

• 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: tert-butyl (S)-2-(4-(octyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S)-3-hydroxy-2-methyl-1-(4-octoxyanilino)-1-oxopropan-2-yl]carbamate
• CAS: 876913-65-4
• 化学式: C₂₃H₃₈N₂O₅
• 分子量: 422.565
• InChiKey: BDGQUGIYMKUHIN-QHCPKHFHSA-N

物化性质

• 沸点：
  604.4±55.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-2-(4-(octyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate 在 草酰氯 、 palladium 10% on activated carbon 、 水 、 氢气 、 二甲基亚砜 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Exploring amino acids derivatives as potent, selective, and direct agonists of sphingosine-1-phosphate receptor subtype-1

  摘要：

  In the quest to discover a potent and selective class of direct agonists to the sphingosine-1-phosphate receptor, we explored the carboxylate functional group as a replacement to previously reported lead phosphates. This has led to the discovery of potent and selective direct agonists with moderate to substantial in vivo lymphopenia. The previously reported selectivity enhancing moiety (SEM) and selectivity enhancing orientation (SEO) in the phenylamide and phenylimidazole scaffolds were crucial to obtaining selectivity for S1P receptor subtype 1 over 3. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.053
• 作为产物：
  描述：

  1-溴辛烷 在 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (S)-2-(4-(octyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate
  参考文献：
  名称：

  强大的鞘氨醇-1-磷酸受体亚型-1激动剂烷氧基-苯基酰胺和烷氧基-苯基咪唑的合成与评价

  摘要：

  在有效和选择性的鞘氨醇-1-磷酸受体激动剂的设计中，我们能够鉴定出基于FTY-720的苯酰胺和苯基咪唑类似物的两个分子系列。这些支架中的几种设计分子已证明对S1P受体亚型1和3具有选择性，并且在小鼠中具有出色的体内活性。口服时，两个分子PPI-4621（4b）和PPI-4691（10a）表现出剂量反应性淋巴细胞减少。

  DOI：

  10.1016/j.bmcl.2008.11.072

文献信息

• [EN] METHODS AND COMPOSITIONS FOR MODULATING SPHINGOSINE-1-PHOSPHATE (S1P) RECEPTOR ACTIVITY<br/>[FR] PROCEDES ET COMPOSITIONS SERVANT A MODULER L'ACTIVITE DU RECEPTEUR DE LA SPHINGOSINE-1-PHOSPHATE (S1P)
  申请人：PRAECIS PHARM INC

  公开号：WO2006020951A1

  公开（公告）日：2006-02-23

  The present invention relates to compounds which modulate the activity of the SI P1 receptor, the use of these compounds for treating conditions associated with signaling through the S1 P1 receptor, and pharmaceutical compositions comprising these compounds.

  本发明涉及调节SI P1受体活性的化合物，以及利用这些化合物治疗与S1 P1受体信号传导相关的疾病的用途，以及包含这些化合物的药物组合物。
• Methods and compositions for modulating sphingosine -1- phosphate (S1P) receptor activity
  申请人：Saha K. Ashis

  公开号：US20080064662A1

  公开（公告）日：2008-03-13

  The present invention relates to compounds which modulate the activity of the S1P1 receptor, the use of these compounds for treating conditions associated with signaling through the S1P1 receptor, and pharmaceutical compositions comprising these compounds.

  本发明涉及调节S1P1受体活性的化合物，使用这些化合物治疗与S1P1受体信号有关的疾病，并包括这些化合物的制药组合物。
• US7241812B2
  申请人：——

  公开号：US7241812B2

  公开（公告）日：2007-07-10
• Synthesis and evaluation of alkoxy-phenylamides and alkoxy-phenylimidazoles as potent sphingosine-1-phosphate receptor subtype-1 agonists
  作者：Ghotas Evindar、Sylvie G. Bernier、Malcolm J. Kavarana、Elisabeth Doyle、Jeanine Lorusso、Michael S. Kelley、Keith Halley、Amy Hutchings、Albion D. Wright、Ashis K. Saha、Gerhard Hannig、Barry A. Morgan、William F. Westlin

  DOI：10.1016/j.bmcl.2008.11.072

  日期：2009.1

  In the design of potent and selective sphingosine-1-phosphate receptor agonists, we were able to identify two series of molecules based on phenylamide and phenylimidazole analogs of FTY-720. Several designed molecules in these scaffolds have demonstrated selectivity for S1P receptor subtype 1 versus 3 and excellent in vivo activity in mouse. Two molecules PPI-4621 (4b) and PPI-4691 (10a), demonstrated

  在有效和选择性的鞘氨醇-1-磷酸受体激动剂的设计中，我们能够鉴定出基于FTY-720的苯酰胺和苯基咪唑类似物的两个分子系列。这些支架中的几种设计分子已证明对S1P受体亚型1和3具有选择性，并且在小鼠中具有出色的体内活性。口服时，两个分子PPI-4621（4b）和PPI-4691（10a）表现出剂量反应性淋巴细胞减少。
• Exploring amino acids derivatives as potent, selective, and direct agonists of sphingosine-1-phosphate receptor subtype-1
  作者：Ghotas Evindar、Hongfeng Deng、Sylvie G. Bernier、Elisabeth Doyle、Jeanine Lorusso、Barry A. Morgan、William F. Westlin

  DOI：10.1016/j.bmcl.2012.11.053

  日期：2013.1

  In the quest to discover a potent and selective class of direct agonists to the sphingosine-1-phosphate receptor, we explored the carboxylate functional group as a replacement to previously reported lead phosphates. This has led to the discovery of potent and selective direct agonists with moderate to substantial in vivo lymphopenia. The previously reported selectivity enhancing moiety (SEM) and selectivity enhancing orientation (SEO) in the phenylamide and phenylimidazole scaffolds were crucial to obtaining selectivity for S1P receptor subtype 1 over 3. (C) 2012 Elsevier Ltd. All rights reserved.