mono-6^A-succinyl-β-cyclodextrin | 144383-79-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: mono-6^A-succinyl-β-cyclodextrin
• 英文别名: mono-succinyl-β-cyclodextrin；4-oxo-4-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-5,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-10-yl]methoxy]butanoic acid
• CAS: 144383-79-9
• 化学式: C₄₆H₇₄O₃₈
• 分子量: 1235.07
• InChiKey: TYRUOHHVSNFLBY-MZIFCKCGSA-N

物化性质

• 熔点：
  182 °C
• 沸点：
  1579.8±65.0 °C(Predicted)
• 密度：
  1.613±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -15
• 重原子数：
  84
• 可旋转键数：
  12
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  597
• 氢给体数：
  21
• 氢受体数：
  38

反应信息

• 作为反应物：
  描述：

  mono-6^A-succinyl-β-cyclodextrin 、 D-phenylalanine cyanoethylester 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  Enantioselective folding at the cyclodextrin surface

  摘要：

  水溶液中β-环糊精连接的L-和D-苯丙氨酸氰乙基酯的光谱和动力学研究揭示了一种不寻常的分子内络合模式，其中氨基酸的疏水部分位于宿主空腔之外； L-和D-衍生物显示出不同的结合几何形状和能量。

  DOI：

  10.1039/c39940002051
• 作为产物：
  描述：

  丁二酸酐 、 β-环糊精 以 吡啶 为溶剂， 以45%的产率得到mono-6^A-succinyl-β-cyclodextrin
  参考文献：
  名称：

  Enantioselective folding at the cyclodextrin surface

  摘要：

  水溶液中β-环糊精连接的L-和D-苯丙氨酸氰乙基酯的光谱和动力学研究揭示了一种不寻常的分子内络合模式，其中氨基酸的疏水部分位于宿主空腔之外； L-和D-衍生物显示出不同的结合几何形状和能量。

  DOI：

  10.1039/c39940002051
• 作为试剂：
  描述：

  异氰环已烷 、 3-氨基吲唑 、 5-溴靛红 在 mono-6^A-succinyl-β-cyclodextrin 作用下， 以 水 为溶剂， 反应 0.58h， 以95%的产率得到2-bromo-14-(cyclohexylamino)indazolo[3',2':2,3]imidazo[1,5-c]quinazolin-6(5H)-one
  参考文献：
  名称：

  Succinyl-β-cyclodextrin–driven synthesis of a nitrogen-fused five-ring heterocycle using GBB-based [4 + 1] cycloaddition via supramolecular host–guest interactions

  摘要：

  We synthesized a mono-succinyl-beta-cyclodextrin (Suc-beta-CD) and used it as a supramolecular organic acid catalyst for the synthesis of the therapeutically relevant indazolo[3',2':2,3]imidazo[1,5-c]quinazolin-6(5H)-one (IIQ) via the Groebke-Blackburn-Bienayme reaction (GBB). The Suc-beta-CD was characterized using MALDI-TOF mass spectrometry, NMR spectroscopy, FT-IR spectroscopy, and SEM. A possible reaction mechanism via molecular complexation is suggested, based on 2D NMR (ROESY) spectroscopy, FT-IR spectroscopy, FE-SEM, and DSC analysis. The significant advantages of this atom-economical method include the simple single-step preparation of the catalyst, tolerance of a wide range of functional groups, easy catalyst recyclability, and absence of a tedious workup or purification; moreover, this method eschews the use of hazardous reagents/solvents. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.12.059

文献信息

• A novel polyrotaxane-based delivery system for scutellarin: preparation, characterization, and in vitro evaluation
  作者：Rui-Jian Jiang、Bo Yang、Zhen-Kun Liu、Yu-Lin Zhao、Xia-Li Liao、Jian Yang、Chuan-Zhu Gao、Fen Wang、Bin Han

  DOI：10.1016/j.carres.2013.07.009

  日期：2013.10

  The safe and effective polyrotaxane-based drug delivery system could potentially increase the antiproliferative activity of antitumor medicine. A novel scutellarin-polyrotaxane (SCU-PR), in which scutellarin (SCU) was covalently bound to one of the hydroxyl groups of polyrotaxane (PR), was synthesized, and its characterization was further investigated by NMR, XRD, TG, DSC. The cytotoxicity of SCU-PR was assessed in vitro using human HCT116 and LOVO cell lines in results that the IC50 values of SCU-PR (1.03 x 10 (6) and 1.01 x 10 (6) mol/L, respectively), which compared with those of free SCU (7.80 x 10 (5) and 7.70 x 10 (5) mol/L, respectively), were lower. The valuable properties of SCU-PR will be potentially useful for its application on human colon cancer chemotherapies. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
• Succinyl-β-cyclodextrin–driven synthesis of a nitrogen-fused five-ring heterocycle using GBB-based [4 + 1] cycloaddition via supramolecular host–guest interactions
  作者：Vijay Vilas Shinde、Seunho Jung

  DOI：10.1016/j.tet.2018.12.059

  日期：2019.2

  We synthesized a mono-succinyl-beta-cyclodextrin (Suc-beta-CD) and used it as a supramolecular organic acid catalyst for the synthesis of the therapeutically relevant indazolo[3',2':2,3]imidazo[1,5-c]quinazolin-6(5H)-one (IIQ) via the Groebke-Blackburn-Bienayme reaction (GBB). The Suc-beta-CD was characterized using MALDI-TOF mass spectrometry, NMR spectroscopy, FT-IR spectroscopy, and SEM. A possible reaction mechanism via molecular complexation is suggested, based on 2D NMR (ROESY) spectroscopy, FT-IR spectroscopy, FE-SEM, and DSC analysis. The significant advantages of this atom-economical method include the simple single-step preparation of the catalyst, tolerance of a wide range of functional groups, easy catalyst recyclability, and absence of a tedious workup or purification; moreover, this method eschews the use of hazardous reagents/solvents. (C) 2019 Elsevier Ltd. All rights reserved.
• Enantioselective folding at the cyclodextrin surface
  作者：Alexey V. Eliseev、Guillermo A. Iacobucci、Nikolai A. Khanjin、F. M. Menger

  DOI：10.1039/c39940002051

  日期：——

  Spectroscopic and kinetic studies of β-cyclodextrin-linked L- and D-phenylalanine cyanoethyl esters in aqueous solution reveal an unusual intramolecular complexation mode where the hydrophobic portion of the amino acid resides outside the host cavity; L- and D-derivatives show different binding geometries and energies.

  水溶液中β-环糊精连接的L-和D-苯丙氨酸氰乙基酯的光谱和动力学研究揭示了一种不寻常的分子内络合模式，其中氨基酸的疏水部分位于宿主空腔之外； L-和D-衍生物显示出不同的结合几何形状和能量。