Pyridin-4-ylmethyl-carbamic acid (E)-(2S,3R)-2-(2,2-dimethyl-propionylamino)-3-hydroxy-octadec-4-enyl ester | 342649-88-1

• 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: Pyridin-4-ylmethyl-carbamic acid (E)-(2S,3R)-2-(2,2-dimethyl-propionylamino)-3-hydroxy-octadec-4-enyl ester
• 英文别名: [(E,2S,3R)-2-(2,2-dimethylpropanoylamino)-3-hydroxyoctadec-4-enyl] N-(pyridin-4-ylmethyl)carbamate
• CAS: 342649-88-1
• 化学式: C₃₀H₅₁N₃O₄
• 分子量: 517.753
• InChiKey: GXNKJCGBXLXLTK-HXYYQIRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  37
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Pyridin-4-ylmethyl-carbamic acid (E)-(2S,3R)-2-(2,2-dimethyl-propionylamino)-3-hydroxy-octadec-4-enyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 Pyridin-4-ylmethyl-carbamic acid (2S,3R)-2-(2,2-dimethyl-propionylamino)-3-hydroxy-octadecyl ester
  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：

  2-N-pivaloyl-3-O-t-butyldimethylsilyl-D-erythro-sphingosine 在 吡啶 、 氢氟酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 Pyridin-4-ylmethyl-carbamic acid (E)-(2S,3R)-2-(2,2-dimethyl-propionylamino)-3-hydroxy-octadec-4-enyl ester
  参考文献：
  名称：

  Sphingomyelin analogues as inhibitors of sphingomyelinase

  摘要：

  To search for neutral sphingomyelinase inhibitors we designed and synthesized hydrolytically stable analogues of sphingomyelin. The novel compounds 8 and 9 which were replaced the phosphodiester moiety of sphingomyelin with the carbamate moiety showed inhibitory activity with an IC50 value of muM on neutral sphingomyelinase in rat brain microsomes. Compound 8i showed a selective neutral sphingomyelinase inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00360-3

文献信息

• Sphingomyelin analogues as inhibitors of sphingomyelinase
  作者：Minoru Taguchi、Kikuo Sugimoto、Ken-ichi Goda、Tomoko Akama、Kyoko Yamamoto、Taizo Suzuki、Yasumitsu Tomishima、Mariko Nishiguchi、Koshi Arai、Kenzo Takahashi、Takeo Kobori

  DOI：10.1016/s0960-894x(03)00360-3

  日期：2003.6

  To search for neutral sphingomyelinase inhibitors we designed and synthesized hydrolytically stable analogues of sphingomyelin. The novel compounds 8 and 9 which were replaced the phosphodiester moiety of sphingomyelin with the carbamate moiety showed inhibitory activity with an IC50 value of muM on neutral sphingomyelinase in rat brain microsomes. Compound 8i showed a selective neutral sphingomyelinase inhibitory activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Biological evaluation of sphingomyelin analogues as inhibitors of sphingomyelinase
  作者：Minoru Taguchi、Ken-ichi Goda、Kikuo Sugimoto、Tomoko Akama、Kyoko Yamamoto、Taizo Suzuki、Yasumitsu Tomishima、Mariko Nishiguchi、Koshi Arai、Kenzo Takahashi、Takeo Kobori

  DOI：10.1016/j.bmcl.2003.08.020

  日期：2003.11

  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.