25,26,27,28-tetrakis[3-(phthalimido)propoxy]calix[4]arene | 858971-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 25,26,27,28-tetrakis[3-(phthalimido)propoxy]calix[4]arene
• 英文别名: 1,3-alternate-25,26,27,28-tetra[(3-phthalimidopropyl)oxy]-calix[4]arene；25,26,27,28-tetrakis-(3-N-phthalimido)propoxycalix[4]arene；25,26,27,28-tetrakis(3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy)calix[4]arene；25,26,27,28-tetra[(3-phthalimidopropyl)oxy]calix[4]arene；2-[3-[[26,27,28-Tris[3-(1,3-dioxoisoindol-2-yl)propoxy]-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]propyl]isoindole-1,3-dione
• CAS: 858971-68-3
• 化学式: C₇₂H₆₀N₄O₁₂
• 分子量: 1173.29
• InChiKey: DIGNBTJBEWHSJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  88
• 可旋转键数：
  20
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  25,26,27,28-tetrakis[3-(phthalimido)propoxy]calix[4]arene 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以90%的产率得到1,3-alternate-25,26,27,28-tetra[(3-aminopropyl)oxy]-calix[4]arene
  参考文献：
  名称：

  合成和杯的电化学性质[4]芳烃含二茂铁单位的衍生物锥体和1,3-交替构象

  摘要：

  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。

  DOI：

  10.1016/j.tet.2011.10.117
• 作为产物：
  描述：

  N-(3-溴丙基)苯二胺 、 25,27-bis[(3-phthalimidopropyl)oxy]-calix[4]arene 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以65%的产率得到25,26,27,28-tetrakis[3-(phthalimido)propoxy]calix[4]arene
  参考文献：
  名称：

  合成和杯的电化学性质[4]芳烃含二茂铁单位的衍生物锥体和1,3-交替构象

  摘要：

  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。

  DOI：

  10.1016/j.tet.2011.10.117

文献信息

• Calixarene-Based Picolinamide Extractants for Selective An/Ln Separation from Radioactive Waste
  作者：Alessandro Casnati、Nicola Della Ca'、Marco Fontanella、Francesco Sansone、Franco Ugozzoli、Rocco Ungaro、Karine Liger、Jean-Francois Dozol

  DOI：10.1002/ejoc.200400793

  日期：2005.6

  Eleven novel ligands having picolinamide or thiopicolinamide binding groups at the upper or lower rim of calix[4]-, calix[6]- and calix[8]arenes have been synthesised. The conformational properties of some of these ligands were studied in solution by means of NMR spectroscopy and in the solid state by X-ray diffraction. Their ability to extract AmIII or EuIII from water to NPHE (o-nitrophenyl hexyl

  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)
• 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。
• 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.
• Lower Rim Guanidinocalix[4]arenes: Macrocyclic Nonviral Vectors for Cell Transfection
  作者：Valentina Bagnacani、Valentina Franceschi、Laura Fantuzzi、Alessandro Casnati、Gaetano Donofrio、Francesco Sansone、Rocco Ungaro

  DOI：10.1021/bc2006829

  日期：2012.5.16

  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.
• 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。