N-[(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(3-pyridin-4-ylmethyl-thioureidomethyl)-heptadec-3-enyl]-2,2-dimethyl-propionamide | 342655-67-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(3-pyridin-4-ylmethyl-thioureidomethyl)-heptadec-3-enyl]-2,2-dimethyl-propionamide
• CAS: 342655-67-8
• 化学式: C₃₆H₆₆N₄O₂SSi
• 分子量: 647.097
• InChiKey: SGTYMKVSBVATRD-BZGIPGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.22
• 重原子数：
  44.0
• 可旋转键数：
  21.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.28
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(3-pyridin-4-ylmethyl-thioureidomethyl)-heptadec-3-enyl]-2,2-dimethyl-propionamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到N-[(E)-(1S,2R)-2-Hydroxy-1-(3-pyridin-4-ylmethyl-thioureidomethyl)-heptadec-3-enyl]-2,2-dimethyl-propionamide
  参考文献：
  名称：

  Biological evaluation of sphingomyelin analogues as inhibitors of sphingomyelinase

  摘要：

  Seeking neutral sphingomyelinase inhibitors, we designed and synthesized hydrolytically stable analogues of sphingomyelin. These novel analogues replace the phosphodiester moiety of sphingomyelin with carbamate and urea moiety, resulting in inhibition of neutral sphingomyelinase. Compound I prevented ceramide generation and apoptotic neuronal cell death in a model of ischemia based on organotypic hippocampal slice cultures. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.020
• 作为产物：
  描述：

  N-((6S,7R)-9,9,10,10-tetramethyl-2-oxo-7-((E)-pentadec-1-en-1-yl)-3,8-dioxa-4-aza-9-silaundec-4-en-6-yl)pivalamide 在 吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 为溶剂， 生成 N-[(E)-(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(3-pyridin-4-ylmethyl-thioureidomethyl)-heptadec-3-enyl]-2,2-dimethyl-propionamide
  参考文献：
  名称：

  Biological evaluation of sphingomyelin analogues as inhibitors of sphingomyelinase

  摘要：

  Seeking neutral sphingomyelinase inhibitors, we designed and synthesized hydrolytically stable analogues of sphingomyelin. These novel analogues replace the phosphodiester moiety of sphingomyelin with carbamate and urea moiety, resulting in inhibition of neutral sphingomyelinase. Compound I prevented ceramide generation and apoptotic neuronal cell death in a model of ischemia based on organotypic hippocampal slice cultures. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.020