AC1MOXS7 | 114847-11-9

• 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: AC1MOXS7
• 英文别名: meso-2,4,6-tri-O-benzyl-D-myo-inositol-1,3,5-O-orthoformate；myo-inositol 1,3,5-orthoformate tribenzyl ether；2,4,6-tri-O-benzyl-myo-inositol orthoformate
• CAS: 114847-11-9
• 化学式: C₂₈H₂₈O₆
• 分子量: 460.527
• InChiKey: QIKGPDYILNCGHY-BWQSURFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  AC1MOXS7 在 sodium hydride 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 6,7-二氮杂二螺[2.1.4.2]十一烷(9CI)
  参考文献：
  名称：

  Synthesis of 1-O-(2-oxo-benzo-1,3,2-dioxaphosphaocan-2-yl)-myo-inositol and 3,5-dideoxy-1-O-(2-oxo-benzo-1,3,2-dioxaphosphaocan-2-yl)-myo-inositol as prodrugs of inositolmonophosphatase ligands

  摘要：

  1-O-(2-oxo-benzo-1,3,2-dioxaphosphaocan-2-yl)-myo-inositol and 3,5-dideoxy-1-O-(2-oxo-benzo -1,3,2 -dioxaphosphaocan- 2 -yl) -myo -inositol were prepared by selective modifications of myo-inositol. Phosphorylation used the phosphite method by means of the 2(N,N-di-isopropylamino).benzo-1,3,2-dioxaphosphaocane. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00941-1
• 作为产物：
  描述：

  myo-Inositol monoorthoformate 在 sodium hydride 作用下， 生成 AC1MOXS7
  参考文献：
  名称：

  Billington, David C.; Baker, Raymond; Kulagowski, Janusz J., Journal of the Chemical Society. Perkin transactions I, 1989, p. 1423 - 1429

  摘要：

  DOI：

文献信息

• Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications
  作者：Wenhong Li、Carsten Schultz、Juan Llopis、Roger Y. Tsien

  DOI：10.1016/s0040-4020(97)00714-x

  日期：1997.9

  inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (), hexakis(propionyloxymethyl) ester () and hexakis(butyryloxymethyl) ester () were therefore synthesized. Whereas extracellular application of up to 200 μM of or to 1321N1 astrocytoma

  肌醇多磷酸的膜渗透性衍生物是用于生物学研究的有用工具。外消旋2,3,6-三-O-丁酰基肌肌醇1,4,5-三磷酸六（乙酰氧基甲基）酯（），肌醇肌醇1,4,5-三磷酸六（乙酰氧基甲基）酯（），六因此合成了（丙酰氧基甲基）酯（）和六（丁酰氧基甲基）酯（）。而最多200μM或1321N1星形细胞瘤细胞的细胞外应用未能动员内部钙，并分别以低至20μM和2μM的浓度释放内部钙。
• Synthesis and antitumor activity of inositol phosphotriester analogues
  作者：Fanbo Song、Jing Zhang、Yuefang Zhao、Wenbin Chen、Luyuan Li、Zhen Xi

  DOI：10.1039/c2ob00031h

  日期：——

  Inositol phosphates, as important second messengers of signal transduction, regulate many biological functions. However, cell penetration and phospholipase stability could be two main issues faced by inositol phosphate analogues used as lead compounds for drug discovery. Inositol phosphotriester analogues could be more beneficial to diffuse across plasma membrane. In this paper, we describe the design and synthesis of a series of inositol phosphotriester analogues based on phosphatidylinositol, along with the initial antitumor activity analysis. Several compounds exhibited good cytotoxic activity against human cancer cell lines A549, HepG2, MDA-MB-231 and HeLa, especially compound 33 was cytotoxic against all the four cancer cell lines with good IC50 values.

  肌醇磷酸盐作为一种重要的信号转导第二信使，调控许多生物学功能。然而，细胞穿透性和磷脂酶稳定性可能是以肌醇磷酸盐类似物作为先导化合物进行药物发现时面临的两个主要问题。肌醇磷酸三酯类似物可能更有利于穿透细胞膜。本文中，我们描述了一系列基于磷脂酰肌醇的肌醇磷酸三酯类似物的设计与合成，以及初步的抗肿瘤活性分析。几种化合物对A549、HepG2、 MDA-MB-231和HeLa这些人类癌细胞系表现出良好的细胞毒性，特别是化合物33对全部四种癌细胞系均显示出细胞毒性，并具有良好的IC50值。
• Establishment of the Structure of Pinpollitol by Total Synthesis of the Proposed Putative Structures
  作者：Kana M. Sureshan、Yutaka Watanabe、Tomohiro Murakami

  DOI：10.1055/s-2005-863752

  日期：——

  Proposed structures of pinpollitol, namely 1,4-di-O-methyl-chiro-inositol and 1,3-di-O-methyl-chiro-inositol, have been synthesized from myo-inositol. Racemic 1,4-di-O-methyl-chiro-inositol has been synthesized from the readily available l,2:4,5-di-O-isopropylidene-myo-inositol, in five steps while DL-1,3-di-O-methyl-chiro-inositol from myo-inositol 1,3,5-orthoformate in nine steps. A comparison of

  pinpollitol 的拟议结构，即 1,4-二-O-甲基-手性-肌醇和 1,3-二-O-甲基-手性-肌醇，已从肌醇合成。外消旋 1,4-二-O-甲基-手性肌醇已从现成的 1,2:4,5-二-O-异亚丙基-肌醇合成五步，而 DL-1,3-二-O-甲基-手性-肌醇来自肌醇 1,3,5-原甲酸酯，分九步。将 pinpollitol 的 NMR 数据与合成二甲醚的 NMR 数据进行比较，表明 pinpollitol 是 D-1,4-二-O-甲基-手性肌醇。因此，我们不仅明确地确认了 pinpollitol 的结构，而且还通过六步从廉价的起始材料肌醇实现了它的快速全合成。
• A Short and Efficient Route from myo- to neo-Inositol
  作者：Pablo Wessig、Kristian Möllnitz、Sebastian Hübner

  DOI：10.1055/s-0029-1220071

  日期：2010.6

  An efficient route from myo- to neo-inositol is described. The key steps of the sequence are oxidation of the hydroxy group at C-5 to the corresponding ketone, followed by a highly (dr = 7.8:1) stereoselective reduction. The route includes nine steps with an overall yield of 51% and is therefore superior to all hitherto reported methods for the preparation of neo-inositol.

  描述了从肌醇到新肌醇的有效途径。该序列的关键步骤是将 C-5 处的羟基氧化为相应的酮，然后进行高度 (dr = 7.8:1) 立体选择性还原。该路线包括 9 个步骤，总收率为 51%，因此优于迄今为止所有报道的制备新肌醇的方法。
• Total synthesis of new 1,5-bissubstituted myo-inositol derivatives. Synthesis of D-myo-inositol 1,5-bisphosphate, 3,5-bisphosphate and of rac. 1,5-Bissulphated and 1,5-bissulphamoylated isosteric analogues
  作者：Pieter Westerduin、Henrica A.M. Willems、Constant A.A. van Boeckel

  DOI：10.1016/s0040-4039(00)97206-x

  日期：1990.1

  Convenient synthesis of D-myo-inositol 1,5-bisphosphate, 3,5-bisphosphate and isosteric rac. 1,5-bissulphate and 1,5-bissulphonamide was accomplished from key intermediate 2,3,4,6-tetra-O-benzyl-myo-inositol.

  D-肌醇1，5-双磷酸酯，3，5-双磷酸酯和等排rac的便捷合成。从关键中间体2,3,4,6-四-O-苄基-肌醇制备了1,5-双硫酸盐和1,5-双磺酰胺。