hexakis(6-bromo-6-deoxy)-α-cyclodextrin | 53784-82-0

• 物质功能分类: 化学试剂 - 有机试剂 - 环糊精
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexakis(6-bromo-6-deoxy)-α-cyclodextrin
• 英文别名: (1S,3S,5S,6S,8S,10S,11S,13S,15S,16S,18S,20S,21S,23S,25S,26S,28S,30S,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-5,10,15,20,25,30-hexakis(bromomethyl)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontane-31,32,33,34,35,36,37,38,39,40,41,42-dodecol
• CAS: 53784-82-0
• 化学式: C₃₆H₅₄Br₆O₂₄
• 分子量: 1350.23
• InChiKey: PYIHGELJTCLTHO-RWMJIURBSA-N

物化性质

• 熔点：
  230-234 °C
• 沸点：
  1368.6±60.0 °C(Predicted)
• 密度：
  1.948±0.06 g/cm3(Predicted)
• 溶解度：
  Soluble in DMF, DMSO. Insoluble in water, methanol, chloroform.
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  66
• 可旋转键数：
  6
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  354
• 氢给体数：
  12
• 氢受体数：
  24

安全信息

• 储存条件：
  存于阴凉干燥处。

反应信息

• 作为反应物：
  描述：

  hexakis(6-bromo-6-deoxy)-α-cyclodextrin 在 sodium tetrahydroborate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以86%的产率得到hexakis(6-deoxy)cyclomaltohexaose
  参考文献：
  名称：

  Improved preparation of hexakis(6-deoxy)cyclomalto-hexaose and heptakis(6-deoxy)cyclomaltoheptaose

  摘要：

  DOI：

  10.1016/s0008-6215(00)90568-8
• 作为产物：
  描述：

  α-环糊精 在 溴甲烯基二甲基溴化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 hexakis(6-bromo-6-deoxy)-α-cyclodextrin
  参考文献：
  名称：

  有效表面上环糊精的表面衍生化

  摘要：

  为了证明使用Vilsmeier-Haack试剂对α，β和γCD进行表面官能化的效率和易用性，已报道了通过全6-溴6-脱氧CD合成13种环糊精（CD）衍生物。

  DOI：

  10.1016/0040-4039(96)00916-1

文献信息

• An improved synthesis of 6-deoxyhalo cyclodextrins via halomethylenemorpholinium halides Vilsmeier-Haack type reagents
  作者：Kazimierz Chmurski、Jacques Defaye

  DOI：10.1016/s0040-4039(97)10019-3

  日期：1997.10

  Per(6-bromo-6-deoxy)cyclomalto-hexaose, -heptaose, and -octaose and the corresponding per(6-chloro-6-deoxy) derivatives were prepared in high yield by reaction of bromomethylenemorpholinium bromide or chloromethylenemorpholinium chloride, respectively, with cyclomaltohexaose, cyclomaltoheptaose and cyclomaltooctaose in dimethylformamide.

  通过分别使溴化亚甲基吗啉溴化物或氯代亚​​甲基吗啉鎓反应高产率地制备每（6-溴-6-脱氧）环麦芽六糖，-庚糖和-八糖以及相应的每-（6-氯-6-脱氧）衍生物，在二甲基甲酰胺中含有环麦芽六糖，环麦芽七糖和环麦芽八糖。
• Bilayer Vesicles of Amphiphilic Cyclodextrins: Host Membranes That Recognize Guest Molecules
  作者：Patrick Falvey、Choon Woo Lim、Raphael Darcy、Tobias Revermann、Uwe Karst、Marcel Giesbers、Antonius T. M. Marcelis、Adina Lazar、Anthony W. Coleman、David N. Reinhoudt、Bart Jan Ravoo

  DOI：10.1002/chem.200400905

  日期：2005.2.4

  Molecular recognition of a hydrophobic anion (adamantane carboxylate) by the cyclodextrin vesicles was investigated by using capillary electrophoresis, thereby exploiting the increase in electrophoretic mobility that occurs when the hydrophobic anions bind to the nonionic cyclodextrin vesicles. It was found that in spite of the presence of oligo(ethylene glycol) substituents, the beta-cyclodextrin vesicles

  两亲环糊精家族（6、7）是通过α-，β-和γ-环糊精（PEG =聚（乙二醇））。这些环糊精在水溶液中形成非离子双层囊泡。通过透射电子显微镜，动态光散射，染料封装和毛细管电泳对双层囊泡进行了表征。通过使用沉积在玻璃上的双层的小角度X射线衍射和在空气-水界面上从Langmuir单层获得的压力-面积等温线，研究了两亲环糊精的分子堆积。双层厚度取决于链长，而平均分子表面积与环糊精环的大小成比例。双层中环糊精的烷基链深交指。通过使用毛细管电泳研究了环糊精囊泡对疏水性阴离子（金刚烷羧酸酯）的分子识别，从而利用了当疏水性阴离子与非离子环糊精囊泡结合时发生的电泳迁移率的增加。发现尽管存在低聚（乙二醇）取代基，β-环糊精囊泡仍保持其对金刚烷羧酸盐的特征亲和力（缔合常数K（a）= 7.1 x 10（3）M（-1））， γ-环糊精囊泡的亲和力较小（K（a）= 3.2 x 10（3）M（-1）），而α-环糊精或非
• [EN] CYCLODEXTRINS AS PROCOAGULANTS<br/>[FR] CYCLODEXTRINES COMME PROCOAGULANTS
  申请人：STICHTING SANQUIN BLOEDVOORZIENING

  公开号：WO2017188820A1

  公开（公告）日：2017-11-02

  The invention relates to substituted cyclodextrins comprising at least one substituent -S-(Cn-alkylene)-R and pharmaceutically acceptable salts thereof, pharmaceutical compositions, kits of parts and their use as procoagulants. The invention further relates to said cyclodextrins for use in methods of reversing an anticoagulant effect of an anticoagulant in a subject, in methods for reducing or preventing bleeding in a subject and in methods for the treatment or prevention of a blood coagulation disorder.

  该发明涉及含有至少一个取代基-S-(Cn-烷基)-R的取代环糊精及其药用可接受的盐、制药组合物、零部件组合套件及其作为促凝剂的用途。该发明还涉及所述环糊精用于在受试者中逆转抗凝剂的抗凝效应的方法、用于减少或预防受试者出血的方法以及用于治疗或预防血液凝固障碍的方法。
• Direct Synthesis of Amphiphilic α-, β-, and γ-Cyclodextrins
  作者：Kazimierz Chmurski、Antony W. Coleman、Janusz Jurczak

  DOI：10.1080/07328309608005692

  日期：1996.9

  ABSTRACT The clean one step synthesis of the amphiphilic α-, β-, and γ-cyclodextrins starting from per-(6-bromo-6-deoxy)-α-, -β-, and -γ-cyclodextrins is described. The role of the lipophilic tail is played by various aryl groups (phenyl, p-bromophenyl, p-O-butoxyphenyl, p-pentylphenyl, and o-, m-, and p-nitrophenyl) linked by a thioether bridge to the position C-6 of each glucopyranose unit. The yields

  摘要描述了从全-（6-溴-6-脱氧）-α-，-β-和-γ-环糊精开始的两亲性α-，β-和γ-环糊精的干净的一步合成。亲脂性尾巴的作用是通过硫醚桥连接到位置C-6的各种芳基（苯基，对溴苯基，对氧丁氧基苯基，对戊基苯基以及邻，间和对硝基苯基）发挥的。每个吡喃葡萄糖单位。S-烷基化反应的产率非常高（85-95％）。
• Per(6-guanidino-6-deoxy)cyclodextrins: synthesis, characterisation and binding behaviour toward selected small molecules and DNA
  作者：Nikolaos Mourtzis、Kyriaki Eliadou、Chrysie Aggelidou、Vassiliki Sophianopoulou、Irene M. Mavridis、Konstantina Yannakopoulou

  DOI：10.1039/b614899a

  日期：——

  Per(6-guanidino-6-deoxy)-cyclodextrins 4a, 4b and 4c are novel derivatives, resulting from homogeneous introduction of the guanidino group at the primary side of α-, β- and γ-cyclodextrins. The products were obtained from the corresponding amino derivatives, as direct guanidinylation of the known bromo-cyclodextrins provided mixtures. The new compounds were fully characterized by NMR spectroscopy and other analytical methods, and their interaction with guest molecules was studied. Strong complexation with 4-nitrophenyl phosphate (NPP) disodium salt was observed (Kbinding ∼5 × 104 M–1), whereas the non-phosphorylated substrate nitrobenzene (NB) formed a very weak complex. 2D ROESY spectra revealed cavity inclusion in both cases, however the orientation of NPP was opposite to that of NB, such that the phosphate group is oriented toward the primary side facing the guanidine groups. The strong affinity of 4 towards the phosphorylated guest suggested that interaction with DNA was possible. The new compounds were found to completely inhibit the migration of ultra pure calf thymus DNA during agarose gel electrophoresis, whereas no effects were observed with guanidine alone or with the plain cyclodextrins. Further, the condensation of DNA into nanoparticles in the presence of 4b was demonstrated by atomic force microscopy, confirming strong electrostatic interaction between the biopolymer and the multicationic products 4. The strong guanidine–phosphate interactions between 4 and DNA were therefore attributed to the clustering of the guanidine groups in the primary area of the cyclodextrin. Cavity effects could not be assessed.

  过(6-胍基-6-脱氧)-环糊精 4a、4b 和 4c 是新型衍生物，是在α-、β-和γ-环糊精的原边均匀引入胍基后得到的。这些产物是从相应的氨基衍生物中获得的，因为直接对已知的溴环糊精进行胍基化会产生混合物。通过核磁共振光谱和其他分析方法对新化合物进行了全面鉴定，并研究了它们与客体分子的相互作用。观察到了与 4-硝基苯磷酸（NPP）二钠盐的强络合（Kbinding ∼5 × 104 M-1），而与非磷酸化底物硝基苯（NB）形成的络合非常弱。二维 ROESY 光谱显示这两种情况下都存在空腔包合，但 NPP 的方向与 NB 相反，即磷酸基团朝向面向胍基团的一侧。4 对磷酸化客体具有很强的亲和力，这表明它有可能与 DNA 发生相互作用。研究发现，在琼脂糖凝胶电泳过程中，新化合物能完全抑制超纯小牛胸腺 DNA 的迁移，而单独使用胍基或普通环糊精则没有任何效果。此外，原子力显微镜还证明了 DNA 在 4b 的存在下凝结成纳米颗粒，证实了生物聚合物与多聚产物 4 之间强烈的静电相互作用。因此，4 和 DNA 之间强烈的胍磷酸盐相互作用归因于环糊精初级区域的胍基团聚集。空穴效应无法评估。