1-(4-azidobutanoyl)-4-(1,3-bis(dihydroxyphosohoryloxy)propan-2-yloxy)-7-nitroindoline | 927866-59-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 1-(4-azidobutanoyl)-4-(1,3-bis(dihydroxyphosohoryloxy)propan-2-yloxy)-7-nitroindoline
• 英文别名: [2-[[1-(4-Azidobutanoyl)-7-nitro-2,3-dihydroindol-4-yl]oxy]-3-phosphonooxypropyl] dihydrogen phosphate
• CAS: 927866-59-9
• 化学式: C₁₅H₂₁N₅O₁₂P₂
• 分子量: 525.306
• InChiKey: OZMYLJUCWMNICI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  223
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-(4-azidobutanoyl)-4-(1,3-bis(dihydroxyphosohoryloxy)propan-2-yloxy)-7-nitroindoline 在 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1-(4-aminobutanoyl)-4-[1,3-bis(dihydroxyphosphoryloxy)propan-2-yloxy]-7-nitroindoline
  参考文献：
  名称：

  Synthesis of an anionically substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors

  摘要：

  A 7-nitroindolin-1-yl amide of the neuroactive amino acid gamma-aminobutryate (GABA) has been synthesised with two phosphate groups attached to the indoline nucleus at 4-alkoxy substituent. The compound is designed to release GABA on a sub-microsecond time scale in response to flash photolysis with near-UV light. The presence of the high negatively charged substituent shows evidence that interaction of the GABA conjugate with ionotropic GABA receptors is much reduced in comparison with an earlier nitroindoline-GABA compound that had no charged groups on the indoline nucleus. In experiments to develop the eventual synthetic route, an unusual reductive cleavage of a TBDMS ether was observed as a significant side reaction during reduction of an indole to an indoline with NaBH3CN in glacial acetic acid. In the eventual synthetic route, the primary amine of GABA was masked as an azide until the final stage of the synthesis, which overcame significant problems with other forms of amine protection. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.030
• 作为产物：
  描述：

  diethyl 2-(indol-4-yloxy)malonate 在 吡啶 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 焦磷酰氯 、 乙酸酐 、 sodium cyanoborohydride 、 copper(II) nitrate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 6.03h， 生成 1-(4-azidobutanoyl)-4-(1,3-bis(dihydroxyphosohoryloxy)propan-2-yloxy)-7-nitroindoline
  参考文献：
  名称：

  Synthesis of an anionically substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors

  摘要：

  A 7-nitroindolin-1-yl amide of the neuroactive amino acid gamma-aminobutryate (GABA) has been synthesised with two phosphate groups attached to the indoline nucleus at 4-alkoxy substituent. The compound is designed to release GABA on a sub-microsecond time scale in response to flash photolysis with near-UV light. The presence of the high negatively charged substituent shows evidence that interaction of the GABA conjugate with ionotropic GABA receptors is much reduced in comparison with an earlier nitroindoline-GABA compound that had no charged groups on the indoline nucleus. In experiments to develop the eventual synthetic route, an unusual reductive cleavage of a TBDMS ether was observed as a significant side reaction during reduction of an indole to an indoline with NaBH3CN in glacial acetic acid. In the eventual synthetic route, the primary amine of GABA was masked as an azide until the final stage of the synthesis, which overcame significant problems with other forms of amine protection. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.030

文献信息

• Anionically substituted 7-Nitroindoline derivatives and their uses
  申请人：Medical Research Council

  公开号：EP1757585B1

  公开（公告）日：2010-12-01
• US7737169B2
  申请人：——

  公开号：US7737169B2

  公开（公告）日：2010-06-15
• Synthesis of an anionically substituted nitroindoline-caged GABA reagent that has reduced affinity for GABA receptors
  作者：George Papageorgiou、John E.T. Corrie

  DOI：10.1016/j.tet.2007.07.030

  日期：2007.9

  A 7-nitroindolin-1-yl amide of the neuroactive amino acid gamma-aminobutryate (GABA) has been synthesised with two phosphate groups attached to the indoline nucleus at 4-alkoxy substituent. The compound is designed to release GABA on a sub-microsecond time scale in response to flash photolysis with near-UV light. The presence of the high negatively charged substituent shows evidence that interaction of the GABA conjugate with ionotropic GABA receptors is much reduced in comparison with an earlier nitroindoline-GABA compound that had no charged groups on the indoline nucleus. In experiments to develop the eventual synthetic route, an unusual reductive cleavage of a TBDMS ether was observed as a significant side reaction during reduction of an indole to an indoline with NaBH3CN in glacial acetic acid. In the eventual synthetic route, the primary amine of GABA was masked as an azide until the final stage of the synthesis, which overcame significant problems with other forms of amine protection. (c) 2007 Elsevier Ltd. All rights reserved.