3-hexyl-4-[(2R)-2-hydroxytridecyl]oxetan-2-one | 1227308-34-0

• 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: 3-hexyl-4-[(2R)-2-hydroxytridecyl]oxetan-2-one
• CAS: 1227308-34-0
• 化学式: C₂₂H₄₂O₃
• 分子量: 354.574
• InChiKey: RSOUWOFYULUWNE-QNGMFEMESA-N

物化性质

• 沸点：
  467.9±18.0 °C(Predicted)
• 密度：
  0.935±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-[(2R)-2-[tert-butyl(dimethyl)silyl]oxytridecyl]-3-hexyloxetan-2-one 在 氢氟酸 作用下， 以 乙腈 为溶剂， 以10%的产率得到3-hexyl-4-[(2R)-2-hydroxytridecyl]oxetan-2-one
  参考文献：
  名称：

  Activity-Based Proteome Profiling of Potential Cellular Targets of Orlistat − An FDA-Approved Drug with Anti-Tumor Activities

  摘要：

  Orlistat, or tetrahydrolipstatin (THL), is an FDA-approved antiobesity drug with potential antitumor activities. Cellular off-targets and potential side effects of Orlistat in cancer therapies, however, have not been extensively explored thus far. In this study, we report the total of synthesis of THL-like protein-reactive probes, in which extremely conservative modifications (i.e., an alkyne handle) were introduced in the parental THL structure to maintain the native biological properties of Orlistat, while providing the necessary functionality for target identification via the bio-orthogonal click chemistry. With these natural productlike, cell-permeable probes, we were able to demonstrate, for the first time, this chemical proteomic approach is suitable for the identification of previously unknown cellular targets of Orlistat. In addition to the expected fatty acid synthase (FAS), we identified a total of eight new targets, some of which were further validated by experiments including Western blotting, recombinant protein expression, and site-directed mutagenesis. Our findings have important implications in the consideration of Orlistat as a potential anticancer drug at its early stages of development for cancer therapy. Our strategy should be broadly useful for off-target identification against quite a number of existing drugs and/or candidates, which are also covalent modifiers of their biological targets.

  DOI：

  10.1021/ja907716f

文献信息

• PROCESS FOR MAKING (2S, 3S, 5S) OXETANONE DERIVATIVES
  申请人：——

  公开号：US20020045767A1

  公开（公告）日：2002-04-18

  This invention relates to novel processes for making (2S, 3S, 5S) oxetanone derivative lipase inhibitor compounds and intermediates therefor, which processes for producing such derivatives that are useful as lipase inhibitors are capable of being scaled to commercial quantities. Further the invention relates to processes for producing salts and for producing pharmaceutical compositions compounds comprising at least one such oxetanone derivative or salt, as well as methods for using such compounds and compositions for inhibiting lipases.

  本发明涉及一种制备(2S,3S,5S)氧杂环己酮衍生物脂肪酶抑制剂化合物及其中间体的新工艺，这些用于生产这种衍生物的工艺能够扩展到商业规模，其制备的衍生物可用作脂肪酶抑制剂。此外，本发明还涉及制备盐和制备含有至少一种这种氧杂环己酮衍生物或盐的药物组合物的工艺，以及使用这些化合物和组合物抑制脂肪酶的方法。
• Process for making (2S, 3S, 5S) oxetanone derivatives
  申请人：——

  公开号：US20020058822A1

  公开（公告）日：2002-05-16

  This invention relates to novel processes for making (2S, 3S, 5S) oxetanone derivative lipase inhibitor compounds and intermediates therefor, which processes for producing such derivatives that are useful as lipase inhibitors are capable of being scaled to commercial quantities. Further the invention relates to processes for producing salts and for producing pharmaceutical compositions compounds comprising at least one such oxetanone derivative or salt, as well as methods for using such compounds and compositions for inhibiting lipases.

  本发明涉及制备（2S, 3S, 5S）氧杂环戊酮衍生物脂肪酶抑制剂化合物及其中间体的新工艺，用于生产这些衍生物的工艺能够扩大到商业规模，这些衍生物是有用的脂肪酶抑制剂。此外，本发明还涉及制备盐和制备至少包含一种这样的氧杂环戊酮衍生物或盐的药物组合物的工艺，以及使用这些化合物和组合物抑制脂肪酶的方法。
• US6392061B1
  申请人：——

  公开号：US6392061B1

  公开（公告）日：2002-05-21
• [EN] PROCESS FOR MAKING (2S, 3S, 5S) OXETANONE DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES D'OXETANONE (2S, 3S, 5S)
  申请人：MULLINS JOHN JASON GENTRY

  公开号：WO2002032850A1

  公开（公告）日：2002-04-25

  This invention relates to novel processes for making (2S, 3S, 5S) oxetanone derivative lipase inhibitor compounds and intermediates therefor, which processes for producing such derivatives that are useful as lipase inhibitors are capable of being scaled to commercial quantities. Further the invention relates to processes for producing salts and for producing pharmaceutical compositions compounds comprising at least one such oxetanone derivative or salt, as well as methods for using such compounds and compositions for inhibiting lipases.