(R,E)-N-(1-hydroxy-4-(tridecylthio)but-3-en-2-yl)octanamide | 1379462-69-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R,E)-N-(1-hydroxy-4-(tridecylthio)but-3-en-2-yl)octanamide
• 英文别名: N-[(E,2R)-1-hydroxy-4-tridecylsulfanylbut-3-en-2-yl]octanamide
• CAS: 1379462-69-7
• 化学式: C₂₅H₄₉NO₂S
• 分子量: 427.736
• InChiKey: NYZFADNSXWSJDZ-PPEFQKSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  29
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  辛酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R,E)-N-(1-hydroxy-4-(tridecylthio)but-3-en-2-yl)octanamide
  参考文献：
  名称：

  3-Deoxy-3,4-dehydro analogs of XM462. Preparation and activity on sphingolipid metabolism and cell fate

  摘要：

  Three analogs of the dihydroceramide desaturase inhibitor XM462 are reported. The compounds inhibit both dihydroceramide desaturase and acid ceramidase, but with different potencies depending on the N-acyl moiety. Other enzymes of sphingolipid metabolism, such as neutral ceramidase, acid sphingomyelinase, acid glucosylceramide hydrolase, sphingomyelin synthase and glucosylceramide synthase, are not affected. The effect on the sphingolipidome of the two best inhibitors, namely (R,E)-N-(1-hydroxy-4-(tridecylthio) but-3-en-2-yl)octanamide (RBM2-1B) and (R, E)-N-(1-hydroxy-4-(tridecylthio) but-3-en-2-yl) pivalamide (RBM2-1D), is in accordance with the results obtained in the enzyme assays. These two compounds reduce cell viability in A549 and HCT116 cell lines with similar potencies and both induced apoptotic cell death to similar levels than C8-Cer in HCT116 cells. The possible therapeutic implications of the activities of these compounds are discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.073

文献信息

• 3-Deoxy-3,4-dehydro analogs of XM462. Preparation and activity on sphingolipid metabolism and cell fate
  作者：Luz Camacho、Fabio Simbari、Maria Garrido、José Luis Abad、Josefina Casas、Antonio Delgado、Gemma Fabriàs

  DOI：10.1016/j.bmc.2012.03.073

  日期：2012.5

  Three analogs of the dihydroceramide desaturase inhibitor XM462 are reported. The compounds inhibit both dihydroceramide desaturase and acid ceramidase, but with different potencies depending on the N-acyl moiety. Other enzymes of sphingolipid metabolism, such as neutral ceramidase, acid sphingomyelinase, acid glucosylceramide hydrolase, sphingomyelin synthase and glucosylceramide synthase, are not affected. The effect on the sphingolipidome of the two best inhibitors, namely (R,E)-N-(1-hydroxy-4-(tridecylthio) but-3-en-2-yl)octanamide (RBM2-1B) and (R, E)-N-(1-hydroxy-4-(tridecylthio) but-3-en-2-yl) pivalamide (RBM2-1D), is in accordance with the results obtained in the enzyme assays. These two compounds reduce cell viability in A549 and HCT116 cell lines with similar potencies and both induced apoptotic cell death to similar levels than C8-Cer in HCT116 cells. The possible therapeutic implications of the activities of these compounds are discussed. (C) 2012 Elsevier Ltd. All rights reserved.