(2S,3R)-2-(tert-butoxycarbonylamino)-14-O-[4'-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol | 727975-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S,3R)-2-(tert-butoxycarbonylamino)-14-O-[4'-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol
• 英文别名: tert-butyl N-[(E,2S,3R)-1,3-dihydroxy-14-[4-[3-(trifluoromethyl)diazirin-3-yl]phenoxy]tetradec-4-en-2-yl]carbamate
• CAS: 727975-09-9
• 化学式: C₂₇H₄₀F₃N₃O₅
• 分子量: 543.627
• InChiKey: OPJSWAPXRIQTQK-ASTIYFOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-(tert-butoxycarbonylamino)-14-O-[4'-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到(2S,3R)-2-amino-14-O-[4'-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol
  参考文献：
  名称：

  Total Synthesis of Two Photoactivatable Analogues of the Growth-Factor-Like Mediator Sphingosine 1-Phosphate:  Differential Interaction with Protein Targets

  摘要：

  The first synthesis of two photoreactive analogues of the lipid mediator and second messenger sphingosine 1-phosphate (S1P), [P-32]-labeled (2S,3R)-14-O-(4'-benzoylphenyl)- and (2S,3R)-14-O-((4'-trifluoromethyldiazirinyl)phenyl)-(4E)-tetradecenyl-2-amino-3-hydroxy-1-phosphate, is described. The interactions of these probes with the SIP type-1 receptor (S1P(1)) transfected into membranes of rat hepatoma cells and with plasma proteins were analyzed. The S1P(1) receptor interacted in a specific manner with the benzophenone-containing ligand (K-D = 84 +/- 10 nM vs K-D for S1P = 36 +/- 2 nM); in contrast, no saturable specific binding was found with the diazirine-containing ligand. However, the same pattern was found for labeling of plasma proteins by both probes, indicating that different parts of the SIP pharmacophore underlie the interaction of S1P with its receptor and plasma carrier proteins.

  DOI：

  10.1021/jo034828q
• 作为产物：
  描述：

  2,2,2-三氟-1-(4-羟基苯基)乙酮 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 盐酸羟胺 、 氨 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2S,3R)-2-(tert-butoxycarbonylamino)-14-O-[4'-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol
  参考文献：
  名称：

  Total Synthesis of Two Photoactivatable Analogues of the Growth-Factor-Like Mediator Sphingosine 1-Phosphate:  Differential Interaction with Protein Targets

  摘要：

  The first synthesis of two photoreactive analogues of the lipid mediator and second messenger sphingosine 1-phosphate (S1P), [P-32]-labeled (2S,3R)-14-O-(4'-benzoylphenyl)- and (2S,3R)-14-O-((4'-trifluoromethyldiazirinyl)phenyl)-(4E)-tetradecenyl-2-amino-3-hydroxy-1-phosphate, is described. The interactions of these probes with the SIP type-1 receptor (S1P(1)) transfected into membranes of rat hepatoma cells and with plasma proteins were analyzed. The S1P(1) receptor interacted in a specific manner with the benzophenone-containing ligand (K-D = 84 +/- 10 nM vs K-D for S1P = 36 +/- 2 nM); in contrast, no saturable specific binding was found with the diazirine-containing ligand. However, the same pattern was found for labeling of plasma proteins by both probes, indicating that different parts of the SIP pharmacophore underlie the interaction of S1P with its receptor and plasma carrier proteins.

  DOI：

  10.1021/jo034828q

文献信息

• Photoaffinity-labeled sphingomyelin analogs and processes thereof
  申请人：Katsumura Shigeo

  公开号：US20050182265A1

  公开（公告）日：2005-08-18

  A photoaffinity-labeled sphingomyelin analog of the following formula: wherein R 1 is C 1-20 alkylene group, R 5 is C 1-20 alkyl group, aryl group or C 1-6 alkyl group substituted by aryl group, Z is photoaffinity-labeled group and Me is methyl group, or an optically active compound thereof.

  以下公式的光亲和标记鞘磷脂类似物： 其中R1是C1-20烷基基团，R5是C1-20烷基基团、芳基基团或由芳基基团取代的C1-6烷基基团，Z是光亲和标记基团，而Me是甲基基团， 或者是其光学活性化合物。
• Total Synthesis of Two Photoactivatable Analogues of the Growth-Factor-Like Mediator Sphingosine 1-Phosphate:  Differential Interaction with Protein Targets
  作者：Xuequan Lu、Sandor Cseh、Hoe-Sup Byun、Gabor Tigyi、Robert Bittman

  DOI：10.1021/jo034828q

  日期：2003.9.1

  The first synthesis of two photoreactive analogues of the lipid mediator and second messenger sphingosine 1-phosphate (S1P), [P-32]-labeled (2S,3R)-14-O-(4'-benzoylphenyl)- and (2S,3R)-14-O-((4'-trifluoromethyldiazirinyl)phenyl)-(4E)-tetradecenyl-2-amino-3-hydroxy-1-phosphate, is described. The interactions of these probes with the SIP type-1 receptor (S1P(1)) transfected into membranes of rat hepatoma cells and with plasma proteins were analyzed. The S1P(1) receptor interacted in a specific manner with the benzophenone-containing ligand (K-D = 84 +/- 10 nM vs K-D for S1P = 36 +/- 2 nM); in contrast, no saturable specific binding was found with the diazirine-containing ligand. However, the same pattern was found for labeling of plasma proteins by both probes, indicating that different parts of the SIP pharmacophore underlie the interaction of S1P with its receptor and plasma carrier proteins.