(1S,2R,6S,7S,8R,9S)-8-fluoro-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-ol | 129365-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (1S,2R,6S,7S,8R,9S)-8-fluoro-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-ol
• CAS: 129365-58-8
• 化学式: C₁₂H₁₉FO₅
• 分子量: 262.278
• InChiKey: AVZCZGXJKNKEHF-DAORTFEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  D-3-Deoxy-3-fluoro-4-O-methyl-myo-inositol 在 camphor-10-sulfonic acid 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (1S,2R,6S,7S,8R,9S)-8-fluoro-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo[7.3.0.02,6]dodecan-7-ol
  参考文献：
  名称：

  Synthesis and Biological Activity of the D-3-Deoxy-3-fluoro and D-3-Chloro-3-deoxy Analogs of Phosphatidylinositol

  摘要：

  The naturally occurring inositol derivative, L-quebrachitol (1), serves as starting material for the synthesis of D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol (4, 28). Their transformation into the title compounds 22 and 40 (abbreviated as FPI and CPI, respectively) is accomplished by benzylation of all hydroxyl groups but OH-1 to which the phosphatidic acid side chain is subsequently attached using the phosphoramidite protocol, and hydrogenolytic deprotection. Compounds 4 and 28, as reported earlier, exhibit moderate and high selectivity, respectively, in the growth inhibition of v-sis transformed vs wild type murine NIH 3T3 cells if myo-inositol is absent but are inactive in the presence of physiological inositol levels. On the other hand, FPI possesses a nearly 2 orders of magnitude higher activity but no selectivity both in the absence or presence of myo-inositol. CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.

  DOI：

  10.1021/jo00084a010

文献信息

• Synthesis of novel metabolically stable analogues of D-myo-inositol 1,4,5-trisphosphate
  作者：Abdul H. Fauq、Javid H. Zaidi、Robert A. Wilcox、Girlie Varvel、Stefan R. Nahorski、Alan P. Kozikowski、Christophé Erneux

  DOI：10.1016/0040-4039(96)00169-4

  日期：1996.3

  Starting from L-quebrachitol, syntheses and biological activities of three novel analogues of the cellular second messenger D-myo-inositol 1,4,5-trisphosphate (IP3), 1,4-bisphosphate 5-phosphorothioate (1a), 1,5-bisphosphate 4-phosphorothioate (1b), and 1-phosphate 4,5-bisphosphorothioate (1c) are described.

  从L-quebrachitol开始，细胞第二种信使D-肌醇1,3,4,5-三磷酸（IP 3），1,4-二磷酸5-硫代磷酸酯（1a），1的三种新型类似物的合成和生物学活性描述了5-二磷酸4-磷酸硫代磷酸酯（1b）和1-磷酸4,5-二磷酸硫代磷酸酯（1c）。
• Synthesis of the first optically pure, fluorinated inositol 1,4,5-trisphosphate of myo-inositol. Stereochemistry and its effect on calcium(2+) release in Swiss 3T3 cells
  作者：Alan P. Kozikowski、Abdul H. Fauq、Ibrahim A. Aksoy、Markus J. Seewald、Garth Powis

  DOI：10.1021/ja00176a055

  日期：1990.9
• KOZIKOWSKI, ALAN P.;FAUQ, ABDUL H.;AKSOY, IBRAHIM A.;SEEWALD, MARKUS J.;P+, J. AMER. CHEM. SOC., 112,(1990) N0, C. 7403-7404
  作者：KOZIKOWSKI, ALAN P.、FAUQ, ABDUL H.、AKSOY, IBRAHIM A.、SEEWALD, MARKUS J.、P+

  DOI：——

  日期：——