1,3-alternate-25,26,27,28-tetra[(3-aminopropyl)oxy]-calix[4]arene | 858971-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-alternate-25,26,27,28-tetra[(3-aminopropyl)oxy]-calix[4]arene
• 英文别名: 25,26,27,28-tetra[(3-aminopropyl)oxy]calix[4]arene；25,26,27,28-tetrakis(3-aminopropoxy)calix[4]arene；3-[[26,27,28-Tris(3-aminopropoxy)-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl]oxy]propan-1-amine
• CAS: 858971-74-1
• 化学式: C₄₀H₅₂N₄O₄
• 分子量: 652.877
• InChiKey: HZQULRZEBYYCJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-alternate-25,26,27,28-tetra[(3-aminopropyl)oxy]-calix[4]arene 在 盐酸 作用下， 以 水 为溶剂， 反应 0.25h， 生成 25,26,27,28-tetrakis(3-aminopropoxy)calix[4]arene tetrahydrochloride
  参考文献：
  名称：

  Lower Rim Guanidinocalix[4]arenes: Macrocyclic Nonviral Vectors for Cell Transfection

  摘要：

  Guanidinium groups were introduced through a spacer at the lower rim of calix[4]arenes in the cone conformation to give new potential nonviral vectors for gene delivery. Several structural modifications were explored, such as the presence or absence of a macrocyclic scaffold, lipophilicity of the backbone, length of the spacer, and nature of the charged groups, in order to better understand the factors which affect the DNA condensation ability and transfection efficiency of these derivatives. The most interesting compound was a calix[4]arene unsubstituted at the upper rim and having four guanidinium groups linked at the lower rim through a three carbon atom spacer. This compound, when formulated with DOPE, showed low toxicity and transfection efficiency higher than the commercially available lipofectamine LTX in the treatment of human Rhabdomiosarcoma and Vero cells. Most of the investigated compounds showed a tendency to self-aggregate in pure water or in the presence of salts, as evidenced by NMR and AFM studies, and it was found that the ability to condense DNA plasmids in nanometric globules is a necessary but not sufficient condition for transfection. The superiority of macrocyclic vectors over linear Gemini-type analogues and of guanidinium compared to other ammonium head groups in determining the biological activity of the vectors was also ascertained.

  DOI：

  10.1021/bc2006829
• 作为产物：
  描述：

  杯[4]芳烃 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 145.0h， 生成 1,3-alternate-25,26,27,28-tetra[(3-aminopropyl)oxy]-calix[4]arene
  参考文献：
  名称：

  用于从放射性废物中选择性分离 An/Ln 的基于杯芳烃的吡啶甲酰胺萃取剂

  摘要：

  已经合成了 11 种在杯[4]-、杯[6]-和杯[8]芳烃的上缘或下缘具有吡啶甲酰胺或硫代吡啶酰胺结合基团的新型配体。这些配体中的一些的构象特性在溶液中通过核磁共振光谱法和在固态下通过 X 射线衍射进行研究。在不同浓度的 LiNO3、HNO3 和亲脂性二碳化物阴离子 (BrCosan) 下测试了它们从水中提取 AmIII 或 EuIII 到 NPHE（邻硝基苯基己基醚）的能力。与使用模型配体 N-丁基吡啶甲酰胺 (19) 获得的数据相比，数据显示杯芳烃配体的结合位点之间的高度合作。其中一些配体显示出非常高的 Am3+ 分配系数 (DAm > 300)，并且在 pH ≥ 3 时具有良好的 Am/Eu 选择性，这为它们在处理低酸度放射性废物中的应用开辟了有趣的前景。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  DOI：

  10.1002/ejoc.200400793

文献信息

• Calixarenes Incorporating Sulfonamide Moieties: Versatile Ligands for Carbonic Anhydrases Inhibition
  作者：Davide Sbravati、Alessandro Bonardi、Silvia Bua、Andrea Angeli、Marta Ferraroni、Alessio Nocentini、Alessandro Casnati、Paola Gratteri、Francesco Sansone、Claudiu T. Supuran

  DOI：10.1002/chem.202103527

  日期：2022.1.27

  with primary benzensulfonamides demonstrated their ability of inhibiting human Carbonic Anhydrases with significant efficiency and selectivity among different isoforms of the enzymes. A mode of binding where the benzensulfonamide arm penetrates into the funnel of the enzyme active site and interacts with the protein Zn2+ ion is supported by X-ray diffraction data and MD calculations.

  带有以初级苯磺酰胺终止的臂的杯芳烃衍生物证明了它们抑制人碳酸酐酶的能力，并且在酶的不同异构体中具有显着的效率和选择性。X射线衍射数据和MD计算支持苯磺酰胺臂渗透到酶活性位点的漏斗中并与蛋白质Zn 2+离子相互作用的结合模式。
• Novel Triphenylamine Appended 1,3-<i>Alternate</i>-Calix[4]arenes: Synthesis and Characterization
  作者：Serkan Erdemir、Mustafa Yilmaz

  DOI：10.1080/00397911.2012.659830

  日期：2013.6.18

  novel calix[4]arene receptors containing triphenylamine units in 1,3-alternate conformation have been synthesized and characterized in detail. First, the 25,27-dipropoxy-26,28-bis[(3-aminopropyl)oxy]-calix[4]arene 4 and 25,26,27,28-tetra[(3-aminopropyl)oxy]-calix[4]arene 7 were prepared by using convenient reagents. Then, these amino derivatives of calix[4]arene were converted to Schiff base derivatives

  摘要 本研究合成并详细表征了两种新型杯[4]芳烃受体，其含有1,3-交替构象的三苯胺单元。首先，25,27-二丙氧基-26,28-双[(3-氨基丙基)氧基]-杯[4]芳烃4和25,26,27,28-四[(3-氨基丙基)氧基]-杯[ 4]芳烃7是通过使用方便的试剂制备的。然后，使用4-甲酰基三苯胺通过缩合将这些杯[4]芳烃的氨基衍生物转化为附加到杯[4]芳烃(5和8)的三苯胺上的席夫碱衍生物。合成的杯[4]芳烃的1,3-交替构象通过1H和13C NMR分析确定。此外，它们的结构已通过使用 1H 和 13C NMR、红外和元素分析进行​​表征。补充材料可用于本文。去出版商' 的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Synthesis and electrochemical properties of calix[4]arene derivatives containing ferrocene units in the cone and 1,3-alternate conformation
  作者：Serkan Erdemir、Pervin Deveci、Bilge Taner、Ozcan Kocyigit

  DOI：10.1016/j.tet.2011.10.117

  日期：2012.1

  Two novel calix[4]arene receptors containing ferrocene units in cone (L1) and 1,3-alternate (L2) conformations have been synthesized from 25,27-dihydroxy-26,28-bis[(3-aminopropyl)oxy]calix[4]arene 4 or 25,26,27,28-tetra[(3-aminopropyl)oxy]calix[4]arene 6 and ferrocenecarboxaldehyde via condensation, respectively. Their structures have been characterized by 1H, 13C, APT, COSY NMR, FTIR, HSMR, and UV–vis

  两种新型杯[4]芳烃含有二茂铁单元受体锥体（大号1）和1,3-交替（大号2）构象已经从25,27二羟基26,28双合成[（3-氨基丙基）氧基通过缩合反应分别形成] calix [4]芳烃4或25,26,27,28-四[（3-氨基丙基）氧基] calix [4]芳烃6和二茂铁甲醛。它们的结构已通过1 H，13 C，APT，COZY NMR，FTIR，HSMR和UV-vis光谱数据表征。的电化学行为大号1和大号2已在F的存在下进行了研究-，氯- ，溴-，H 2 PO 4 -，CH 3 COO -的阴离子。电化学研究表明，这些受体电化学识别CH 3 COO -，H 2 PO 4 -和Cl - ，阴离子。使用UV-vis研究，证实了在DMSO溶液中对这些阴离子的选择性。
• A Click Ligation Based on SuFEx for the Metal-Free Synthesis of Sugar and Iminosugar Clusters
  作者：Renaud Zelli、Stefano Tommasone、Pascal Dumy、Alberto Marra、Alessandro Dondoni

  DOI：10.1002/ejoc.201600732

  日期：2016.10

  tetra-propylsulfonyl fluoride calixarene, obtained from the free-OH calix[4]arene through a three-step reaction sequence, underwent clean coupling with both C-glucosylpropylamine and N-aminopentyl-1-deoxy-deoxynojirimycin derivatives to give the corresponding tetravalent sugar and iminosugar clusters. This metal-free click reaction may constitute a valuable tool in the arsenal of ligation tools for

  尽管异头糖基磺酰氟的制备不成功，但以相应的硫代乙酸盐为原料，通过形成磺酸盐作为关键中间体合成了四-O-乙酰化的C-葡糖基丙磺酰氟。这种磺酰氟是一种稳定的产品，在 80 °C 下与伯和仲烷基胺迅速反应，以良好的收率得到相应的磺酰胺。另一方面，相同的氟化物对芳胺呈惰性，而其前体磺酰氯则显示出良好的反应性。乙酰化糖磺酰氟的另一个限制是它与多价胺化杯芳烃缺乏反应性，这是由于乙酰基从碳水化合物部分转移到支架的氨基。幸运的是，四-O-苄基化的C-葡萄糖基丙磺酰氟，通过与用于合成乙酰化类似物的相同反应顺序制备，与四氨基丙基杯[4]芳烃反应以高分离产率提供相应的磺酰胺连接的糖簇。合成基于杯芳烃的亚氨基糖簇的类似方法未成功，因为无法生成 1-脱氧野尻霉素磺酰氟衍生物。然而，从游离 OH 杯 [4] 芳烃通过三步反应序列获得的四丙基磺酰氟杯芳烃与 C-葡糖基丙胺和 N-氨基戊基-1-脱氧-脱氧野尻霉素衍生物进
• Macrocyclic Nonviral Vectors: High Cell Transfection Efficiency and Low Toxicity in a Lower Rim Guanidinium Calix[4]arene
  作者：Valentina Bagnacani、Francesco Sansone、Gaetano Donofrio、Laura Baldini、Alessandro Casnati、Rocco Ungaro

  DOI：10.1021/ol801326d

  日期：2008.9.18

  New multivalent cationic lipids, one of them showing high efficiency and low toxicity in cell transfection, have been obtained by attaching guanidinium groups at the lower rim of calix[4]arenes.