(2R,3S,4R)-4-amino-2-tetradecyltetrahydrofuran-3-ol | 1338778-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,3S,4R)-4-amino-2-tetradecyltetrahydrofuran-3-ol
• 英文别名: (2R,3S,4R)-4-amino-2-tetradecyloxolan-3-ol
• CAS: 1338778-21-4
• 化学式: C₁₈H₃₇NO₂
• 分子量: 299.497
• InChiKey: FBQCDJRSCUVUFL-KURKYZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-1-{(4R,5S)-2-oxo-4-[(triisopropylsilyloxy)methyl]oxazolidin-5-yl}pentadecyl acetate 在 甲醇 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三甲胺盐酸盐 、 magnesium 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 (2R,3S,4R)-4-amino-2-tetradecyltetrahydrofuran-3-ol
  参考文献：
  名称：

  Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C

  摘要：

  Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKC zeta and PKC iota) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.061

文献信息

• METHOD OF TREATING OVARIAN CANCER USING A PKC INHIBITOR
  申请人：Acevedo-Duncan Mildred Enid

  公开号：US20150366883A1

  公开（公告）日：2015-12-24

  A method of treating ovarian cancer by administering a PKC inhibitor is presented herein. It was found that administering a PKC inhibitor, such as ACPD or ICA-1, to ovarian cancer cells inhibited cancer cell proliferation.
• US9301965B2
  申请人：——

  公开号：US9301965B2

  公开（公告）日：2016-04-05
• Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C
  作者：Yuji Yoshimitsu、Shinya Oishi、Jun Miyagaki、Shinsuke Inuki、Hiroaki Ohno、Nobutaka Fujii

  DOI：10.1016/j.bmc.2011.07.061

  日期：2011.9

  Sphingosine kinases (SphKs) are oncogenic enzymes that regulate the critical balance between ceramide and sphingosine-1-phosphate. Much effort has been dedicated to develop inhibitors against these enzymes. Naturally occurring pachastrissamine (jaspine B) and all its stereoisomers were prepared and evaluated for their inhibitory effects against SphKs. All eight stereoisomers exhibited moderate to potent inhibitory activity against SphK1 and SphK2. Inhibitory effects were profiled against protein kinase C (PKC) isoforms by in vitro experiments. Atypical PKCs (PKC zeta and PKC iota) were inhibited by several pachastrissamine stereoisomers. The improved activity over N,N-dimethylsphingosine suggests that the cyclic scaffold in pachastrissamines facilitates potential favorable interactions with SphKs and PKCs. (C) 2011 Elsevier Ltd. All rights reserved.