2-N-pivaloyl-D-erythro-sphingosine | 342649-66-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 2-N-pivaloyl-D-erythro-sphingosine
• 英文别名: N-((2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2yl)pivalamide；N-pivaloyl-C18-sphingosine；N-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)pivalamide；N-Pivaloylsphingosine；N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]-2,2-dimethylpropanamide
• CAS: 342649-66-5
• 化学式: C₂₃H₄₅NO₃
• 分子量: 383.615
• InChiKey: SQWMKANURYLEAZ-BWMVHVDHSA-N

物化性质

• 沸点：
  555.6±50.0 °C(Predicted)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-N-pivaloyl-D-erythro-sphingosine 在 吡啶 、 咪唑 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-N-pivaloyl-3-O-t-butyldimethylsilyl-D-erythro-sphingosine
  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
• 作为产物：
  描述：

  D-赤式-鞘氨醇盐酸盐 、 三甲基乙酸 在 1-羟基苯并三唑 、 N-甲基吗啉 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以45%的产率得到2-N-pivaloyl-D-erythro-sphingosine
  参考文献：
  名称：

  [EN] COMPOUNDS, THEIR SYNTHESES, COMPOSITIONS, AND METHODS TO TREAT CANCER
  [FR] COMPOSÉS, LEURS SYNTHÈSES, LEURS COMPOSITIONS ET MÉTHODES POUR TRAITER LE CANCER

  摘要：

  公开号：

  WO2010093615A3

文献信息

• COMPOUNDS, THEIR SYNTHESES, COMPOSITIONS, AND METHODS TO TREAT CANCER
  申请人：Beckman Barbara S.

  公开号：US20120027844A1

  公开（公告）日：2012-02-02

  Compounds and their syntheses are disclosed herein. Compositions and pharmaceutical compositions comprising a compound are also described, and include compositions also comprising liposomes. Methods for the treatment of cancer in animals comprising administering a compound or a composition comprising a compound are also described.

  本文披露了化合物及其合成方法。还描述了包含化合物的组合物和药物组合物，其中包括还包含脂质体的组合物。还描述了用于治疗动物癌症的方法，包括给动物施用化合物或包含化合物的组合物。
• [EN] COMPOUNDS, THEIR SYNTHESES, COMPOSITIONS, AND METHODS TO TREAT CANCER<br/>[FR] COMPOSÉS, LEURS SYNTHÈSES, LEURS COMPOSITIONS ET MÉTHODES POUR TRAITER LE CANCER
  申请人：TULANE UNIVERSITY

  公开号：WO2010093615A3

  公开（公告）日：2010-11-25
• US8853452B2
  申请人：——

  公开号：US8853452B2

  公开（公告）日：2014-10-07
• Novel d-erythro N-octanoyl sphingosine analogs as chemo- and endocrine-resistant breast cancer therapeutics
  作者：James W. Antoon、Jiawang Liu、Adharsh P. Ponnapakkam、Matthew M. Gestaut、Maryam Foroozesh、Barbara S. Beckman

  DOI：10.1007/s00280-009-1233-0

  日期：2010.5

  Resistance to endocrine and chemotherapies remains the primary cause of breast cancer treatment failure. We have synthesized four novel d-erythro N-octanoyl sphingosine analogs and catalogued their activity in drug-sensitive (MCF-7), endocrine-resistant (MDA-MB-231) and chemoresistant (MCF-7TN-R) breast cancer cells.3-(4,5-Dimethylthiazol-2-Yl)-2,5-diphenyltetrazolium bromide (MTT) assay was used to determine cell viability; colony assay was performed to determine effects on clonogenic survival and H-1 NMR, C-13 NMR, HPLC spectra and elemental analytical data analyses were used to determine analog identity and purity.All four analogs inhibited both viability and clonogenic survival, with analog C exhibiting a log-fold improvement in anti-survival activity compared to the parent compound.With resistance to current breast cancer chemotherapies on the rise, the development of novel therapeutic targets is of growing importance. Our results show that lipid analogs have therapeutic potential in treating chemo- and endocrine-resistant breast cancer.
• 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.