1-O-benzoyl-scyllo-inositol | 261621-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-benzoyl-scyllo-inositol
• 英文别名: 1‐O‐benzoyl‐scyllo‐inositol；1-O-benzoyl-2,3,4,5,6-pentahydroxy-scyllo-inositol；1-O-Bz-2,3,4,5,6-pentahydroxyl-scyllo-inositol
• CAS: 261621-51-6
• 化学式: C₁₃H₁₆O₇
• 分子量: 284.266
• InChiKey: USFAYASKIQJDGW-JZWZECNXSA-N

物化性质

• 沸点：
  448.2±45.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.97
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127.45
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-O-benzoyl-scyllo-inositol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以88%的产率得到scyllo-inositol
  参考文献：
  名称：

  Synthesis of all possible regioisomers of scyllo-Inositol phosphate

  摘要：

  scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis-diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo-IPn. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00183-2
• 作为产物：
  描述：

  Inositol 在 palladium dihydroxide 氢气 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 20.0~100.0 ℃ 、344.74 kPa 条件下， 反应 52.0h， 生成 1-O-benzoyl-scyllo-inositol
  参考文献：
  名称：

  Synthesis of all possible regioisomers of scyllo-Inositol phosphate

  摘要：

  scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis-diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo-IPn. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00183-2

文献信息

• Design, Synthesis, and Delivery Properties of Novel Guanidine-Containing Molecular Transporters Built on Dimeric Inositol Scaffolds
  作者：Kaustabh K. Maiti、Ock-Youm Jeon、Woo Sirl Lee、Sung-Kee Chung

  DOI：10.1002/chem.200600898

  日期：2007.1.12

  We have developed a novel class of synthetic molecular transporters that contain eight residues of guanidine with an inositol dimer as the scaffold. The dimers were prepared by connecting two units of myo- or scyllo-inositol via a carbonate or amide linkage, and the multiple units of the guanidine functionality were constructed on the inositol scaffold by means of peracylation with omega-aminocarboxylate

  我们已经开发出一类新型的合成分子转运蛋白，其中包含八个残基的胍基和一个肌醇二聚体作为支架。通过经由碳酸酯或酰胺键连接两个单元的肌醇或鲨肌醇来制备二聚体，并通过用不同长度的ω-氨基羧酸酯衍生物进行过酰基化，在肌醇支架上构建多个胍官能团。基于共聚焦激光扫描显微镜和荧光激活的细胞分选仪分析的生物测定表明，这些转运蛋白表现出不同程度的膜转运能力，并且细胞内定位和小鼠组织分布研究强烈表明，这些转运蛋白经历与迄今为止报道的肽转运蛋白。
• [EN] INOSITOL-BASED MOLECULAR TRANSPORTERS AND PROCESSES FOR THE PREPARATION THEREOF<br/>[FR] TRANSPORTEURS MOLECULAIRES A BASE D'INOSITOL ET LEURS PROCEDES DE PREPARATION
  申请人：POSTECH FOUNDATION

  公开号：WO2005085159A1

  公开（公告）日：2005-09-15

  Inositol derivatives in accordance with the present invention are effective in significantly enhancing the transportation of various therapeutic molecules across a biological membrane, which may include the plasma membrane, nuclear membrane or blood-brain barrier.

  根据本发明，肌醇衍生物在显著增强各种治疗分子穿过生物膜的运输方面是有效的，这些生物膜可能包括细胞膜、核膜或血脑屏障。
• Mitochondrial Affinity of Guanidine-rich Molecular Transporters Built on myo- and scyllo-Inositol Scaffolds: Stereochemistry Dependency
  作者：Subhash C. Ghosh、Bo-Ram Kim、Jung-Kyun Im、Woo-Sirl Lee、Chang-Nim Im、Young-Tae Chang、Wan-Il Kim、Kyong-Tai Kim、Sung-Kee Chung

  DOI：10.5012/bkcs.2010.31.12.3623

  日期：2010.12.20

  We prepared several novel molecular transporters built on myo- and scyllo-inositol scaffolds with variations in the number of guanidine residues, linker chain lengths and patterns. Some of these transporters were found to localize in mitochondria, and the mitochondrial affinity seems to be substantially related to the scaffold stereochemistry.

  我们准备了几种新型分子运输体，这些运输体基于肌醇和斯基洛肌醇架构，具有不同数量的氨基脲残基、连接链长度和排列模式。发现其中一些运输体能够定位于线粒体，而线粒体亲和力似乎与架构的立体化学显著相关。
• Novel Substrates for Kinases Involved in the Biosynthesis of Inositol Pyrophosphates and Their Enhancement of ATPase Activity of a Kinase
  作者：Raja Mohanrao、Ruth Manorama、Shubhra Ganguli、Mithun C. Madhusudhanan、Rashna Bhandari、Kana M. Sureshan

  DOI：10.3390/molecules26123601

  日期：——

  IP6K and PPIP5K are two kinases involved in the synthesis of inositol pyrophosphates. Synthetic analogs or mimics are necessary to understand the substrate specificity of these enzymes and to find molecules that can alter inositol pyrophosphate synthesis. In this context, we synthesized four scyllo-inositol polyphosphates—scyllo-IP5, scyllo-IP6, scyllo-IP7 and Bz-scyllo-IP5—from myo-inositol and studied

  IP6K 和 PPIP5K 是参与肌醇焦磷酸合成的两种激酶。合成类似物或模拟物对于了解这些酶的底物特异性和寻找可以改变肌醇焦磷酸合成的分子是必要的。在这方面，我们合成了4种鲨肌醇polyphosphates-鲨-IP 5，鲨-IP 6，鲨-IP 7和Bz-青蟹-IP 5 -从肌醇肌醇并研究了它们的活性作为鼠标IP6K1和催化底物VIP1 的结构域，PPIP5K 的萌芽酵母变体。我们孵化了这些大闸蟹-肌醇多磷酸盐，这些激酶和 ATP 作为磷酸盐供体。我们通过测量形成的放射性标记的鲨肌醇焦磷酸产物的量和消耗的 ATP 量来跟踪酶活性。所有鲨肌醇磷酸盐是两个激酶的底物，但它们比相应的弱肌肌醇磷酸。我们的研究揭示了轴向羟基/磷酸酯对 IP6K1 底物识别的重要性。我们发现所有这些衍生物都增强了 VIP1 的 ATPase 活性。我们发现 IP6K1 的配体诱导的 ATPase 活性非常弱。苯甲酰基-青蟹-IP
• [EN] INOSITOL AND TREHALOSE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS FOR TREATING NEURODEGENERATIVE DISEASES COMPRISING THE SAME<br/>[FR] DÉRIVÉS D'INOSITOL ET DE TRÉHALOSE ET COMPOSITIONS PHARMACEUTIQUES POUR LE TRAITEMENT DES MALADIES NEURODÉGÉNÉRATIVES COMPRENANT CES DÉRIVÉS
  申请人：POSTECH ACAD IND FOUND

  公开号：WO2010011012A1

  公开（公告）日：2010-01-28

  The invented inositol and trehalose derivatives, prepared by introducing multiple units of the guanidine group to the backbone molecules, show excellent blood-brain barrier permeability, and accordingly, it can be easily transported to the brain tissues and utilized for the treatment of neurodegenerative diseases such as Alzheimer¡s disease and Huntington's disease.

  通过在骨架分子中引入多个胍基单元制备的肌醇和海藻糖衍生物表现出优异的血脑屏障渗透性，因此可以轻松地运输到脑组织并用于治疗神经退行性疾病，如阿尔茨海默病和亨廷顿病。