1,3,5-tris(5-ethylcarbamoyl-1H-pyrrole-2-carboxylic acid benzyl ester)-2,4,6-triethylbenzene | 934824-84-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3,5-tris(5-ethylcarbamoyl-1H-pyrrole-2-carboxylic acid benzyl ester)-2,4,6-triethylbenzene
• 英文别名: 1,3,5-tris(5-methylcarbamoyl-1H-pyrrole-2-benzylcarboxylate)-2,4,6-triethylbenzene；benzyl 5-[[2,4,6-triethyl-3,5-bis[[(5-phenylmethoxycarbonyl-1H-pyrrole-2-carbonyl)amino]methyl]phenyl]methylcarbamoyl]-1H-pyrrole-2-carboxylate
• CAS: 934824-84-7
• 化学式: C₅₄H₅₄N₆O₉
• 分子量: 931.058
• InChiKey: NSPCLNDJPBWVFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  69
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  214
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,5-tris(5-ethylcarbamoyl-1H-pyrrole-2-carboxylic acid benzyl ester)-2,4,6-triethylbenzene 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以0.05 g的产率得到1,3,5-tris(5-ethylcarbamoyl-1H-pyrrole-2-carboxylic acid)-2,4,6-triethylbenzene
  参考文献：
  名称：

  A Molecular Flytrap for the Selective Binding of Citrate and Other Tricarboxylates in Water

  摘要：

  The synthesis and binding properties of a new tricationic guanidiniocarbonyl pyrrole receptor 7 are described. Receptor 7 binds citrate 9 and other tricarboxylates such as trimesic acid tricarboxylate 8 with unprecedented high association constants of K-assoc > 10(5) M-1 in water as determined by UV and fluorescence tritration studies. According to NOESY experiments and molecular modeling calculations, the tricarboxylates are bound within the inner cavity of receptor 7 by ion pairing between the carboxylate groups and the guanidiniocarbonyl pyrrole moieties, favored by the nonpolar microenvironment of the cavity. Hence, receptor 7 can be regarded as a molecular flytrap. In the case of the aromatic tricarboxylate 8, additional aromatic interactions further strengthen the complex. The complexes with the tricarboxylates are so strong that even the presence of a large excess of competing anions or buffer salts does not significantly affect the association constant. For example, the association constant for citrate changes only from K-assoc = 1.6 x 10(5) M-1 in pure water to K-assoc = 8.6 x 10(4) M-1 in the presence of a 170-fold excess of bis-tris buffer and a 1000-fold excess of chloride. This makes 7 one of the most efficient receptors for the binding of citrate in aqueous solvents reported thus far.

  DOI：

  10.1021/ja0433469
• 作为产物：
  描述：

  1H-pyrrole-2,5-dicarboxylic acid monobenzyl ester 、 1,3,5-tris(methylammonium chloride)-2,4,6-triethylbenzene 在 N-甲基吗啉 4-二甲氨基吡啶 、 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 1,3,5-tris(5-ethylcarbamoyl-1H-pyrrole-2-carboxylic acid benzyl ester)-2,4,6-triethylbenzene
  参考文献：
  名称：

  A Molecular Flytrap for the Selective Binding of Citrate and Other Tricarboxylates in Water

  摘要：

  The synthesis and binding properties of a new tricationic guanidiniocarbonyl pyrrole receptor 7 are described. Receptor 7 binds citrate 9 and other tricarboxylates such as trimesic acid tricarboxylate 8 with unprecedented high association constants of K-assoc > 10(5) M-1 in water as determined by UV and fluorescence tritration studies. According to NOESY experiments and molecular modeling calculations, the tricarboxylates are bound within the inner cavity of receptor 7 by ion pairing between the carboxylate groups and the guanidiniocarbonyl pyrrole moieties, favored by the nonpolar microenvironment of the cavity. Hence, receptor 7 can be regarded as a molecular flytrap. In the case of the aromatic tricarboxylate 8, additional aromatic interactions further strengthen the complex. The complexes with the tricarboxylates are so strong that even the presence of a large excess of competing anions or buffer salts does not significantly affect the association constant. For example, the association constant for citrate changes only from K-assoc = 1.6 x 10(5) M-1 in pure water to K-assoc = 8.6 x 10(4) M-1 in the presence of a 170-fold excess of bis-tris buffer and a 1000-fold excess of chloride. This makes 7 one of the most efficient receptors for the binding of citrate in aqueous solvents reported thus far.

  DOI：

  10.1021/ja0433469

文献信息

• Pyrrolic Tripodal Receptors Effectively Recognizing Monosaccharides. Affinity Assessment through a Generalized Binding Descriptor
  作者：Cristina Nativi、Martina Cacciarini、Oscar Francesconi、Alberto Vacca、Gloriano Moneti、Andrea Ienco、Stefano Roelens

  DOI：10.1021/ja068754m

  日期：2007.4.1

  titrations. Both receptors selectively recognized Glc among the investigated monosaccharides, with 3 generally less effective than 4 but showing selectivities for the all-equatorial beta-glycosides of Glc and GlcNAc among the largest reported for H-bonding synthetic receptors. Selectivities in CDCl3 spanned a range of nearly 250-fold for 3 and over 30-fold for 4. Affinities and selectivities were univocally

  吡咯和亚氨基 (3) 或氨基 (4) H 键合配体被纳入苯基三足支架，以开发新一代的碳水化合物分子识别受体。受体 3 和 4 有效结合一组生物相关单糖的辛基糖苷，包括葡萄糖 (Glc)、半乳糖 (Gal)、甘露糖 (Man) 和 N-乙酰氨基葡萄糖 (GlcNAc)，在 CDCl3 中显示出微摩尔亲和力，在CD3CN 通过 NMR 滴定。两种受体都选择性地识别所研究的单糖中的 Glc，其中 3 种通常不如 4 种有效，但显示出对 Glc 和 GlcNAc 的全赤道β-糖苷的选择性，这是报道的最大的 H 键合合成受体。CDCl3 中的选择性范围为 3 的近 250 倍和 4 的 30 倍以上。通过 BC50 描述符对亲和力和选择性进行了统一评估，为此描述了一种广义处理，该处理将描述符的范围扩展到包括具有任意数量结合常数的任何双试剂主客体系统。乙腈中 betaGlc 的 ITC 滴定证明，对于