(R,E)-2-amino-4-(tridecylthio)but-3-en-1-ol | 1266326-14-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R,E)-2-amino-4-(tridecylthio)but-3-en-1-ol
• 英文别名: (E,2R)-2-amino-4-tridecylsulfanylbut-3-en-1-ol
• CAS: 1266326-14-0
• 化学式: C₁₇H₃₅NOS
• 分子量: 301.537
• InChiKey: ITSVTNWZXAHSAR-LCJXNMAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,E)-2-amino-4-(tridecylthio)but-3-en-1-ol 、 Octanoic acid benzotriazol-1-yl ester 在 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
• 作为产物：
  描述：

  1-十三烷硫醇 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 22.0h， 生成 (R,E)-2-amino-4-(tridecylthio)but-3-en-1-ol
  参考文献：
  名称：

  意外获得含有乙烯基硫化物单元的新 Sphingoid 碱基

  摘要：

  描述了对含有乙烯基硫化物单元的新鞘氨醇碱的意外访问。该过程涉及环氧化物与硫醇盐的“一锅”区域选择性打开，然后是分子内酰基转移、碱基促进消除和最终水解。最佳收率需要过量氢化钠和高稀释条件。该过程适用于各种硫醇盐。由此产生的化合物可以被视为新的混合鞘氨醇碱基，它结合了其他报道的鞘脂类似物中存在的一些结构基序。

  DOI：

  10.1055/s-0030-1259047

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.
• An Unexpected Access to a New Sphingoid Base Containing a Vinyl Sulfide Unit
  作者：Antonio Delgado、Ingrid Nieves、María Garrido、José Abad

  DOI：10.1055/s-0030-1259047

  日期：2010.12

  An unexpected access to a new sphingoid base containing a vinyl sulfide unit is described. The process involves the 'one-pot' regioselective opening of an epoxide with a thiolate, followed by intramolecular acyl transfer, base-promoted elimination, and final hydrolysis. Excess sodium hydride and high dilution conditions are required for optimal yields. The process is amenable to a variety of thiolates

  描述了对含有乙烯基硫化物单元的新鞘氨醇碱的意外访问。该过程涉及环氧化物与硫醇盐的“一锅”区域选择性打开，然后是分子内酰基转移、碱基促进消除和最终水解。最佳收率需要过量氢化钠和高稀释条件。该过程适用于各种硫醇盐。由此产生的化合物可以被视为新的混合鞘氨醇碱基，它结合了其他报道的鞘脂类似物中存在的一些结构基序。