2-deoxy-2-fluoro-myo-inositol | 135212-48-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-fluoro-myo-inositol
• CAS: 135212-48-5
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: PDTJJYSBSOKEOY-KXXVROSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.86
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101.15
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1,4,5,6-tetra-O-benzyl-2-deoxy-2-fluoro-myo-inositol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以80%的产率得到2-deoxy-2-fluoro-myo-inositol
  参考文献：
  名称：

  作为糖基磷脂酰肌醇磷脂酶C抑制剂的2-脱氧-2-氟代肌醇-1-0-十二烷基膦酸酯的合成

  摘要：

  已经合成了三种2-脱氧-2-氟代肌醇及其1-0-十二烷基膦酸酯衍生物作为糖基磷脂酰肌醇磷脂酶C的不可裂解的抑制剂。讨论了它们的结构-活性关系。

  DOI：

  10.1016/0040-4039(95)01579-5

文献信息

• Offer, John L.; Voorheis, H. Paul; Metcalfe, James C., Journal of the Chemical Society. Perkin transactions I, 1992, # 8, p. 953 - 960
  作者：Offer, John L.、Voorheis, H. Paul、Metcalfe, James C.、Smith, Gerry A.

  DOI：——

  日期：——
• Synthesis of [3H]-labelled and unlabelled 2-deoxy-2-fluoro-myo-inositol and 1-deoxy-1-fluoro-scyllo-inositol for use in studies of the phosphoinositide cycle
  作者：Gordon Lowe、Fiona McPhee

  DOI：10.1039/p19910001249

  日期：——

  2-Deoxy-2-fluoro-myo-inositol and 1-deoxy-1-fluoro-scyllo-inositol have been synthesized in their unlabelled and tritiated forms in order to study their potential as inhibitors of the phosphoinositide cycle.
• Radiosynthesis and in vivo tumor uptake of 2-deoxy-2-[18F]fluoro-myo-inositol
  作者：Laurence Carroll、Meg Perumal、Neil Vasdev、Edward Robins、Eric O. Aboagye

  DOI：10.1016/j.bmcl.2012.08.022

  日期：2012.10

  Inositols play an important role in membrane lipid metabolism and mitogenic signaling of most cancer cells. There is paucity of data on the distribution of radiolabelled inositols. Based on work previously carried out on 1-deoxy-1-[F-18]fluoro-scyllo-inositol ([F-18]2), we began a program of work to label myo-inositol (2-deoxy-2-[F-18]fluoro-myo-inositol, [F-18]1), the most abundant inositol in cells. Fluorination of a triflate precursor 4 afforded the desired [F-18]1 following deprotection with a radiochemical yield of 8% n.d.c. [F-18]1 showed higher uptake in vivo in a human breast cancer xenograft model, MDA-MB-231, compared to [F-18]2. Thus, we have developed a new inositol radiotracer that could have utility for studying inositol uptake in tumors. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 2-deoxy-2-fluorinated inositol-1-0-dodecylphosphonates as inhibitors of glycosyl phosphatidylinositol phospholipase C
  作者：Hai-Xiao Zhai、Ping-Sheng Lei、James C. Morris、Kojo Mensa-Wilmot、T.Y. Shen

  DOI：10.1016/0040-4039(95)01579-5

  日期：1995.10

  Three 2-deoxy-2-fluorinated inositols and their 1-0-dodecylphosphonate derivatives have been synthesized as non-cleavable inhibitors of glycosyl phosphatidylinositol phospholipase C. Their structure-activity relationship is discussed.

  已经合成了三种2-脱氧-2-氟代肌醇及其1-0-十二烷基膦酸酯衍生物作为糖基磷脂酰肌醇磷脂酶C的不可裂解的抑制剂。讨论了它们的结构-活性关系。