biphenyl-4,4'-disulfonyl-A,D-capped β-cyclodextrin | 73499-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: biphenyl-4,4'-disulfonyl-A,D-capped β-cyclodextrin
• 英文别名: biphenylyl-4,4'-disulfonyl-A,D-capped-β-cyclodextrin；Biphenyl-4,4'-disulfonyl-A,D-capped beta-cyclodextrin；(1R,2R,3R,4S,6R,8R,9S,11R,13R,14S,16R,18R,19S,21R,22R,23R,24S,25R,40R,43S,44R,46R,48S,49R,51R,53R,54R,55R,56R,62R,63R,64R,65R,66R,67R)-8,13,18,44,49-pentakis(hydroxymethyl)-28,28,37,37-tetraoxo-5,7,10,12,15,17,20,27,38,41,42,45,47,50,52,61-hexadecaoxa-28λ6,37λ6-dithiaundecacyclo[22.17.11.26,9.211,14.216,19.229,32.233,36.243,46.248,51.121,25.04,40]heptahexaconta-29,31,33,35,57,59-hexaene-2,3,22,23,53,54,55,56,62,63,64,65,66,67-tetradecol
• CAS: 73499-21-5
• 化学式: C₅₄H₇₆O₃₉S₂
• 分子量: 1413.31
• InChiKey: DTERAHOZRPDYOK-RJULKEFWSA-N

物化性质

• 密度：
  1.615±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -12
• 重原子数：
  95
• 可旋转键数：
  5
• 环数：
  29.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  617
• 氢给体数：
  19
• 氢受体数：
  39

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  biphenyl-4,4'-disulfonyl-A,D-capped β-cyclodextrin 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以92%的产率得到6A,6D-dideoxy-6A,6D-di-iodo-β-cyclodextrin
  参考文献：
  名称：

  [EN] CYCLODEXTRIN BASED POLYMERS, METHODS, COMPOSITIONS AND APPLICATIONS THEREOF
  [FR] POLYMÈRES À BASE DE CYCLODEXTRINE, ET LEURS PROCÉDÉS, COMPOSITIONS ET APPLICATIONS

  摘要：

  本公开涉及包含环糊精或其衍生物与连接子基团的共轭物的聚合物，以及它们在治疗脂质储存疾病中的应用，通过从细胞中去除胆固醇等脂质。具有以下结构的聚合物：Formula (I)，其中CD、L和n在此处定义，展示出改进的特性，包括但不限于改进的生物相容性、改进的保留时间、在细胞中的延长作用时间以及在治疗各种肾脏疾病和相关症状中的增加疗效。

  公开号：

  WO2018051298A1
• 作为产物：
  描述：

  4,4'-联苯二磺酰氯 、 β-环糊精 在 吡啶 作用下， 反应 2.0h， 生成 biphenyl-4,4'-disulfonyl-A,D-capped β-cyclodextrin
  参考文献：
  名称：

  β-环糊精二硫醇盐衍生的 [Fe4S4]2+ 簇的形成、光谱表征和溶液稳定性

  摘要：

  已经研究了衍生自 β-环糊精 (CD) 二硫醇盐的 [Fe 4 S 4 ] 2+簇的形成和溶液性质，包括在混合水-Me 2 SO 介质中的稳定性。[Fe 4 S 4 (SAr) 4 ] 2– (Ar = Ph, C 6 H 4 -3-F)型团簇通过 [Fe 4 S 4 (SEt) 4 ] 的氧化还原反应在 Me 2 SO中生成2–使用 2 当量的 ArSSAr。与 6 A ,6 D -(3-NHCOC6 H 4 -1-SH) 2 -6 A ,6 D -双脱氧-β-环糊精 ( 14 )，其合成得到描述，提供完全取代的簇，公式为 [Fe 4 S 4 {β-CD-(1, 3-NHCOC 6 H 4 S) 2 } 2 ] 2– ( 15 )。配体结合由圆二色光谱以及紫外-可见光和各向同性位移的1 H NMR 光谱以及与 [Fe 4 S 4 (SPh) 4 ] 2–令人信服地相似的氧化还原行为表明.

  DOI：

  10.1021/ic301324u

文献信息

• Cyclodextrin-based polymers for therapeutics delivery
  申请人：Cheng Jianjun

  公开号：US09550860B2

  公开（公告）日：2017-01-24

  The present invention relates to novel compositions of therapeutic cyclodextrin containing polymeric compounds designed as a carrier for small molecule therapeutics delivery and pharmaceutical compositions thereof. These cyclodextrin-containing polymers improve drug stability and solubility, and reduce toxicity of the small molecule therapeutic when used in vivo. Furthermore, by selecting from a variety of linker groups and targeting ligands the polymers present methods for controlled delivery of the therapeutic agents. The invention also relates to methods of treating subjects with the therapeutic compositions described herein. The invention further relates to methods for conducting pharmaceutical business comprising manufacturing, licensing, or distributing kits containing or relating to the polymeric compounds described herein.

  本发明涉及一种新型治疗环糊精含聚合物化合物的组合物，设计为小分子治疗药物的载体以及其制药组合物。这些含环糊精的聚合物提高了药物的稳定性和溶解性，并在体内使用时降低了小分子治疗药物的毒性。此外，通过从各种连接基团和靶向配体中选择，这些聚合物提供了治疗剂的控制释放方法。本发明还涉及使用所述治疗组合物治疗受试者的方法。本发明还涉及进行制药业务的方法，包括制造、许可或分发包含或与本文所述聚合物化合物相关的试剂盒。
• COMPLEXING AGENTS FOR COMPOSITIONS CONTAINING INCLUSION COMPLEXES
  申请人：California Institute of Technology

  公开号：US20170049903A1

  公开（公告）日：2017-02-23

  The invention provides a composition containing particulate composite of a polymer and a therapeutic agent. The composition also contains a complexing agent. The polymer interacts with the complexing agent in a host-guest or a guest-host interaction to form an inclusion complex. A therapeutic composition of the invention may be used to deliver the therapeutic agent and to treat various disorders. Both the polymer of the particulate composite and the complexing agent may be used to introduce functionality into the therapeutic composition. The invention also relates to a method of preparing a composition. The method combines a therapeutic agent, a polymer having host or guest functionality, and a complexing agent having guest or host functionality to form the therapeutic composition. The complexing agent forms an inclusion complex with the polymer. The invention also relates to a method of delivering a therapeutic agent. According to the method, a therapeutically effective amount of a therapeutic composition of the invention is administered to a mammal (e.g. person or animal) in recognized need of the therapeutic. Also disclosed are compounds having the formula:

  该发明提供了一种含有聚合物和治疗剂的颗粒复合物的组合物。该组合物还包含一种络合剂。聚合物与络合剂在宿主-客体或客体-宿主相互作用中相互作用，形成包含复合物。该发明的治疗组合物可用于传递治疗剂并治疗各种疾病。颗粒复合物的聚合物和络合剂均可用于向治疗组合物引入功能。该发明还涉及一种制备组合物的方法。该方法将治疗剂、具有宿主或客体功能的聚合物以及具有客体或宿主功能的络合剂结合在一起，形成治疗组合物。络合剂与聚合物形成包含复合物。该发明还涉及一种传递治疗剂的方法。根据该方法，在确实需要治疗的已知需要治疗的哺乳动物（例如人或动物）体内给予该发明的治疗组合物的治疗有效量。还披露了具有以下结构的化合物：
• Homo- and hetero-difunctionalized β-cyclodextrins: Short direct synthesis in gram scale and analysis of regiochemistry
  作者：Gábor Benkovics、Mihály Bálint、Éva Fenyvesi、Erzsébet Varga、Szabolcs Béni、Konstantina Yannakopoulou、Milo Malanga

  DOI：10.3762/bjoc.15.66

  日期：——

  The regioselective difunctionalization of cyclodextrins (CDs) leading to derivatives amenable to further transformations is a daunting task due to challenging purification and unambiguous characterization of the obtained regioisomers with similar physicochemical properties. The primary-side homo-difunctionalization of β-CD can lead to three regioisomers, while the hetero-difunctionalization can generate three pairs of pseudoenantiomers. Previously, approaches with several synthetic steps, expensive reagents, high purification demands and low yields of the products have been employed. Herein we present direct, short and efficient primary-side difunctionalization strategies featuring reproducibility, ease of product purification, scalability of the reactions and versatility of the substituents introduced. Specifically, the prepared ditosylated β-CDs were separated using preparative reversed-phase column chromatography and their structures were elucidated by NMR experiments. Azidation led to the corresponding pure diazido regioisomers. Direct monotosylation of 6-monoazido-β-CD or monoazidation of the single regioisomers 6^A,6^X-ditosyl-β-CDs afforded hetero-difunctionalized 6^A-monoazido-6^X-tosyl-β-CDs in significant yields. Overall, the single regioisomers, 6^A,6^X-ditosyl-, 6^A,6^X-diazido- and 6^A-monoazido-6^X-monotosyl-β-CD were prepared in one or two steps and purified in multigram scale thus opening the way towards further selective and orthogonal functionalizations of β-CD hosts.

  环糊精（CDs）的区域选择性双官能化导致衍生物易于进一步转化，由于所得到的区异构体具有相似的物理化学性质，挑战性的纯化和明确表征是一项艰巨的任务。β-CD的主侧同官能化可能导致三个区异构体，而异官能化可能产生三对伪对映体。以前采用了几个合成步骤、昂贵试剂、高纯化要求和低产率的方法。在这里，我们提出了直接、简短、高效的主侧双官能化策略，具有可重复性、易于产品纯化、反应可扩展性和引入的取代基的多功能性。具体地，制备的二对甲苯磺酰化β-CDs通过制备性反相柱色谱分离，并通过NMR实验阐明了它们的结构。偶氮化导致了相应的纯二叠氮区异构体。直接对6-单叠氮-β-CD进行单甲苯磺酰化或对单区异构体6A,6X-二对甲苯磺酰-β-CD进行单叠氮化，得到了产量可观的6A-单叠氮-6X-对磺酰-β-CD。总的来说，单区异构体6A,6X-二对甲苯磺酰-、6A,6X-二叠氮-和6A-单叠氮-6X-单对磺酰-β-CD可在一两个步骤中制备，并在多克级规模上纯化，从而为进一步选择性和正交功能化β-CD宿主打开了道路。
• New cyclodextrin dimers and trimers capable of forming supramolecular adducts with shape-specific ligands
  作者：Silvio Aime、Eliana Gianolio、Francesca Arena、Alessandro Barge、Katia Martina、George Heropoulos、Giancarlo Cravotto

  DOI：10.1039/b812172a

  日期：——

  supramolecular adducts. A series of CD dimers and trimers was prepared in good yields by carrying out the critical synthetic steps under power ultrasound (US) or microwave (MW) irradiation. Starting from azide and acetylenic CD derivatives, we exploited an efficient MW-promoted Huisgen 1,3-dipolar cycloaddition in the presence of Cu(I) salts. The resulting bridged CD derivatives gave stable adducts with m

  桥接的环糊精二聚体和三聚体（其中两个和三个疏水性腔非常靠近）显示出比亲代环糊精（CD）高得多的结合亲和力和分子选择性。通过将βCD单元与插入在不同位置（2-2'，3-2'，6-2'或6-2'-6''）的链节连接，并插入不同长度和形状的间隔物，可以合成多腔结构，精确定制以适合特定的客体分子。该酶模拟策略也可用于产生稳定的超分子加合物。通过在功率超声（US）或微波（MW）照射下进行关键的合成步骤，可以高收率制备一系列CD二聚体和三聚体。从叠氮化物和炔属CD衍生物开始，我们开发了一种有效的MW促进的Huisgen 1，在Cu（I）盐存在下的3-偶极环加成反应。所得的桥接CD衍生物与含有g（III）螯合物的磁共振成像造影剂（MRI CA）形成稳定的加合物。发现这些包合物与βCD形成的包合物相比稳定2至3个数量级，并且具有高弛豫值。
• Diisobutylaluminum Hydride Mediated Regioselective O Desilylations: Access to Multisubstituted Cyclodextrins
  作者：Ramprasad Ghosh、Ping Zhang、Aixia Wang、Chang-Chun Ling

  DOI：10.1002/anie.201105737

  日期：2012.2.13

  A face off: Diisobutylaluminum hydride (DIBAL‐H) has been found to be an effective O‐desilylating reagent at the primary face of cyclodextrins. This methodology shows high chemo‐ and regioselectivity and provides an effective route to orthogonally protected, multisubstituted cyclodextrin derivatives.

  值得商off的是：发现二异丁基氢化铝（DIBAL-H）在环糊精的主要表面上是一种有效的O-去甲硅烷基化试剂。该方法显示出高的化学和区域选择性，并为正交保护的多取代环糊精衍生物提供了一条有效途径。