6-deoxy-6-hydroxyethylamino-β-cyclodextrin | 162615-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-6-hydroxyethylamino-β-cyclodextrin
• 英文别名: mono-6-ethanolamino-6-deoxy-β-CD；6-deoxy-6-hydroxylethylamino-β-cyclodextrin；(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)-5-[(2-hydroxyethylamino)methyl]-10,15,20,25,30,35-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]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• CAS: 162615-68-1
• 化学式: C₄₄H₇₅NO₃₅
• 分子量: 1178.07
• InChiKey: IOQDDYPWOGHXKF-LZITWAFGSA-N

物化性质

• 熔点：
  202 °C (decomp)
• 沸点：
  1543.3±60.0 °C(Predicted)
• 密度：
  1.590±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -15.4
• 重原子数：
  80
• 可旋转键数：
  10
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  566
• 氢给体数：
  22
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  二乙烯基砜 、 6-deoxy-6-hydroxyethylamino-β-cyclodextrin 以 水 为溶剂， 反应 1.0h， 以85%的产率得到VSCD
  参考文献：
  名称：

  单乙烯基砜β-环糊精。灵活的毒品运送系统

  摘要：

  环糊精已被缀合以靶向各种受体，并且还已经被碳水化合物官能化以靶向特定器官。但是，这种方法基于严格的设计，这意味着每个环糊精-靶向剂结合物的即席合成。我们假设：1）使载体功能与靶向功能脱钩的模块化设计可形成灵活的系统，2）将乙烯基砜基团对充当靶向剂的生物分子的反应性与环糊精与环糊精形成复合物的能力结合在一起各种各样的药物可能会产生一个通用的系统，该系统可以使用不同的药物靶向不同的器官，3）可以利用组氨酸残基对乙烯基砜基团更高的反应性，以一定的区域选择性将环糊精偶联到靶向系统上。作为概念的证明，我们合成了单乙烯基砜β-环糊精（负责有效负载的模块），在偶联至针对布鲁氏锥虫（负责靶向的模块）和硝呋喃酮（负责治疗作用的模块）的负载导致形成有效的递送系统，该系统靶向寄生虫的表面并显示锥虫活性。

  DOI：

  10.1002/cmdc.201300385
• 作为产物：
  描述：

  6A-叠氮基-6A-脱氧-β-环糊精 、 C.I.酸性橙108 在 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以100%的产率得到6-deoxy-6-hydroxyethylamino-β-cyclodextrin
  参考文献：
  名称：

  An efficient, regioselective and fast enzymatic glycosylation for cyclodextrins

  摘要：

  The introduction of a short spacer arm was necessary to obtain complete regioselectivity in the glycosylation of beta-cyclodextrin (beta-CD) mediated by glycosidases. Thus 6-N-(2-aminoethyl-alpha-D-galactopyranosyl)-6-deoxycyclomaltoheptaose was prepared in four steps from beta-cyclodextrin with 30% overall yield using, in the key step, the transfer activity of green coffee bean alpha-galactosidase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.003
• 作为试剂：
  描述：

  茴香硫醚 在 sodium molybdate dihydrate 、 双氧水 、 6-deoxy-6-hydroxyethylamino-β-cyclodextrin 作用下， 以 水 为溶剂， 反应 8.0h， 生成 甲基苯基亚砜 、 (S)-methylphenylsulfoxide
  参考文献：
  名称：

  Amino alcohol-modified β-cyclodextrin inducing biomimetic asymmetric oxidation of thioanisole in water

  摘要：

  Inspired by beta-CD, a macrocyclic oligomers of D-(+)-glucopyranose and a renewable material, which could be obtained from starch, that can promote a lot of organic reactions in water, a green solvent, several amino alcohol-modified beta-CDs CD-1 to CD-7 were synthesized in the yields of 36-61%. Their conformations in vacuum and in aqueous solution were optimized by quantum calculation. Their complexes with sodium molybdate prepared in situ were characterized by H-1 NMR and were applied in the asymmetric oxidation of thioanisole. Their performance in inducing enantioselectivity was investigated in detail. For the optimal one, CD-1, moderate enantioselectivity (56% ee) was achieved in aqueous CH3COONa-HCl buffer solution (pH 7.0). The abilities of CD-1 to CD-7 to induce asymmetry are highly dependent on the pH value of the reaction medium and the structure of the modifying group. The origin of the moderate enantioselectivity and the reaction mechanism were investigated with the aid of H-1 ROESY NMR studies and quantum calculation. The moderate enantioselectivity was attributed to the two different binding models between CD-1 and thioanisole, which could be defined as intramolecular catalysis and intermolecular catalysis, in which intramolecular catalysis gave (S)-methyl phenyl sulfoxide and intermolecular catalysis gave (R, S)-methyl phenyl sulfoxide. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.03.034

文献信息

• Synthesis of Novel Cyclodextrin Trimers
  作者：Mei-Ming Luo、Wen-Hua Chen、De-Qi Yuan、Ru-Gang Xie

  DOI：10.1080/00397919808004938

  日期：1998.10

  Abstract CD trimers (3 and 6) and CD dimers (4 and 7) have been synthesized by reaction of 6-deoxy-6-hydroxyethylamino-β-CD (1) with corresponding 1,3,5-tri(bromomethyl) benzene (2) or 1,3,5-tri (bromomethyl)-2,4,6-trimethylbenzene (5) in the presence of base.

  摘要 通过 6-脱氧-6-羟乙基氨基-β-CD (1) 与相应的 1,3,5-三（溴甲基）苯反应合成了 CD 三聚体（3 和 6）和 CD 二聚体（4 和 7）。 2) 或 1,3,5-三(溴甲基)-2,4,6-三甲基苯 (5) 在碱存在下。
• Catalytic properties of novel cyclodextrin dimers in the hydrolytic cleavage ofp-nitrophenyl alkanoates
  作者：Mei-Ming Luo、Ru-Gang Xie、Ping-Fang Xia、Ling Tao、De-Qi Yuan、Hua-Ming Zhao

  DOI：10.1002/poc.379

  日期：2001.8

  Novel cyclodextrin (CD) dimers (3a–c) linked by multidentate ligands were prepared by reacting 6-deoxy-6-(hydroxyethylamino)-β-CD (2) with p- and m-bis(bromomethyl)benzene and 2,6-bis(bromomethyl)pyridine, respectively. The catalytic properties of 2, 3b and 3c in the hydrolytic cleavage of p-nitrophenyl alkanoates, namely acetate (PNPA), butanoate (PNPB), hexanoate (PNPH) and octanoate (PNPO), were

  新颖的环糊精（CD）二聚体（3A-C通过齿配体连接）由6-脱氧-6-（羟基乙基氨基）反应，制备-β-CD（2）与p -和米双（溴甲基）苯和2,6- -双（溴甲基）吡啶。的催化性质2，图3b和图3c中的水解裂解p硝基苯基链烷酸酯，即乙酸酯（PNPA），丁酸乙酯（PNPB），己酸盐（PNPH）和辛酸（PNPO），进行了研究。CD二聚体3b和3c在中性附近显示出适度的速率增强。尽管在3b存在下催化速率常数（k c）或3c随酯链长度的变化不显着，“长链”酯（PNPH和PNPO）的米氏常数K M远小于“短链”酯（PHPA和PNPB）的米氏常数，因此，“长链”酯的选择性因子（k c / K M）比“短链”酯的选择性因子大得多，这表明CD二聚体在水解过程中具有良好的尺寸识别能力和底物选择性。对硝基苯基链烷酸酯。向反应介质中添加Cu 2+对K M的影响不大，但导致K M的显着增加。ķ Ç在，因此增加ķ Ç
• Microwave-assisted synthesis of 6-amino-β-cyclodextrins
  作者：Antonino Puglisi、John Spencer、James Clarke、John Milton

  DOI：10.1007/s10847-011-0054-z

  日期：2012.8

  A general microwave-assisted procedure for the synthesis of 6-amino-β-cyclodextrins is reported. Mono-tosyl-β-cyclodextrin was used as the starting material in a one-pot route employing a solvent-free microwave-assisted reaction with a liquid amine. Shorter reaction times were observed for the formation of 6-amino-β-cyclodextrins using this novel microwave approach compared to the thermal procedure.

  本研究报道了一种合成 6-氨基-β-环糊精的通用微波辅助程序。以单对甲苯磺酰基-β-环糊精为起始原料，采用无溶剂微波辅助液胺反应的一锅法。与热反应相比，使用这种新型微波方法生成 6-氨基-β-环糊精的反应时间更短。
• Polyethylenimine–Bisphosphonate–Cyclodextrin Ternary Conjugates: Supramolecular Systems for the Delivery of Antineoplastic Drugs
  作者：Simona Plesselova、Pablo Garcia-Cerezo、Victor Blanco、Francisco J. Reche-Perez、Fernando Hernandez-Mateo、Francisco Santoyo-Gonzalez、María Dolores Giron-Gonzalez、Rafael Salto-Gonzalez

  DOI：10.1021/acs.jmedchem.1c00887

  日期：2021.8.26

  drug-carrying polymers. This work reports the design, synthesis, and biological evaluation of polyethyleneimine–BP–cyclodextrin (PEI-BP-CD) ternary conjugates with supramolecular capabilities for the loading of antineoplastic drugs. A straightforward, modular, and versatile strategy based on the click aza-Michael addition reaction of vinyl sulfones (VSs) allows the grafting of BPs targeting ligands and

  双膦酸盐 (BP) 是骨结合分子，当与载药聚合物结合时，可为骨癌细胞提供靶向能力。这项工作报告了聚乙烯亚胺-BP-环糊精 (PEI-BP-CD) 三元偶联物的设计、合成和生物学评估，该偶联物具有用于装载抗肿瘤药物的超分子能力。基于乙烯基砜 (VSs) 的点击氮杂-迈克尔加成反应的简单、模块化和通用的策略允许将靶向配体和 βCD 载体附件的 BPs 接枝到 PEI 聚合物支架上。在体外对不同骨相关癌细胞系（MC3T3-E1 成骨细胞、MG-63 肉瘤细胞和 MDA-MB-231 乳腺细胞）中三元偶联物及其阿霉素包合物的评估（细胞毒性、细胞摄取、内化途径和亚细胞分布）癌细胞）证实了特异性、线粒体靶向性以及介导靶向药物向这些细胞转运的整体能力。在体内使用MG-63和对小鼠的MDA-MB-231细胞的异种移植物的评价也证实了共轭物的靶向。
• Remote loading of curcumin-in-modified β-cyclodextrins into liposomes using a transmembrane pH gradient
  作者：Fadwa Odeh、Hamdi Nsairat、Walhan Alshaer、Shrouq Alsotari、Rula Buqaien、Said Ismail、Abdalla Awidi、Abeer Al Bawab

  DOI：10.1039/c9ra07560g

  日期：——

  The current study provides a novel remote loading approach utilizing chemically modified cyclodextrins to incorporate hydrophobic drugs into liposomes.

  当前研究提供了一种新颖的远程装载方法，利用化学修饰的环糊精将疏水药物纳入脂质体中。