benzyl 3,5-diaminobenzoate | 261724-01-0

• 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: benzyl 3,5-diaminobenzoate
• CAS: 261724-01-0
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: DNSGVXFULSASMN-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C
• 沸点：
  481.7±30.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3,5-diaminobenzoate 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 3,5-Bis-[2-({(S)-1-[2-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-pyrrolidine-2-carbonyl}-amino)-acetylamino]-benzoic acid benzyl ester
  参考文献：
  名称：

  α-Galactose based neoglycopeptides. Inhibition of verotoxin binding to globotriosylceramide

  摘要：

  Solution and solid phase strategies for the synthesis of a-galactose based neoglycopeptide derivatives 2-13 were developed. Neoglycopeptides generated were tested for the inhibition of verotoxin binding to globotriosylceramide (Gb3) using ELISA. Among all of the compounds tested, only the lipid derivatives of neoglycopeptides, 11, 12 and 13 were found to be inhibitors, IC50 = 2.0 mM (11b and 12c) and 0.2 mM (11c and 13c). All of the inhibitors (11b, 11c, 12c and 13c) have a similar branching of the two alpha-galactosyl units at the N-terminal glycine residue of a short peptide and a lipid moiety attached at the C-terminal site. Both of these factors seem to be crucial for the inhibition. It is interesting to note that the inhibitors have only a portion of the natural trisaccharide ligand. The secondary groups either may contribute in sub-site oriented interactions with the protein receptors or may mimic the internal sugar units of the cell-surface ligand, Gb3. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00226-6
• 作为产物：
  描述：

  3,5-双-boc-氨基苯甲酸 在 18-冠醚-6 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 48.0h， 生成 benzyl 3,5-diaminobenzoate
  参考文献：
  名称：

  Improving the gelation properties of 3,5-diaminobenzoate-based organogelators in aromatic solvents with additional aromatic-containing pendants

  摘要：

  A family of 3,5-diaminobenzoate derivatives containing different Cbz-protected alpha- or beta-amino side pendant chains and different aromatic-containing ester functionalities was prepared. It was found that the additional aromatic rings in the Cbz- and aromatic-containing ester moieties significantly improved the gelation properties of the resulting organogelators in aromatic solvents. Infrared and circular dichroism spectroscopy revealed that both H-bonding and pi-pi aromatic stacking interactions were the main driving forces for gelation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.066

文献信息

• [EN] COMPOUNDS COMPRISING PARAMAGNETIC CHELATES ARRANGED AROUND A CENTRAL CORE AND THEIR USE IN MAGNETO RESONANCE IMAGING AND SPECTROSCOPY<br/>[FR] COMPOSÉS COMPRENANT DES CHÉLATES PARAMAGNÉTIQUES DISPOSÉS AUTOUR D'UN COER CENTRAL ET LEUR UTILISATION EN IMAGERIE ET SPECTROSCOPIE PAR RÉSONANCE MAGNÉTIQUE
  申请人：GE HEALTHCARE AS

  公开号：WO2009127715A1

  公开（公告）日：2009-10-22

  The present invention relates to novel compounds of formula (I) and (II), compositions comprising compounds of formula (II) and their use as contrast agents in magnetic resonance (MR) imaging (MRI) and MR spectroscopy (MRS).

  本发明涉及具有式(I)和(II)的新化合物，包含式(II)化合物的组合物，以及它们作为磁共振成像（MRI）和磁共振波谱（MRS）对比剂的用途。
• COMPOUNDS COMPRISING PARAMAGNETIC CHELATES ARRANGED AROUND A CENTRAL CORE AND THEIR USE IN MAGNETO RESONANCE IMAGING AND SPECTROSCOPY
  申请人：Meijer Andreas

  公开号：US20110038805A1

  公开（公告）日：2011-02-17

  The present invention relates to novel compounds of formula (I) and (II), compositions comprising compounds of formula (II) and their use as contrast agents in magnetic resonance (MR) imaging (MRI) and MR spectroscopy (MRS).
• US9828548B2
  申请人：——

  公开号：US9828548B2

  公开（公告）日：2017-11-28
• Improving the gelation properties of 3,5-diaminobenzoate-based organogelators in aromatic solvents with additional aromatic-containing pendants
  作者：Hak-Fun Chow、Jie Zhang、Chui-Man Lo、Siu-Yin Cheung、Ka-Wai Wong

  DOI：10.1016/j.tet.2006.10.066

  日期：2007.1

  A family of 3,5-diaminobenzoate derivatives containing different Cbz-protected alpha- or beta-amino side pendant chains and different aromatic-containing ester functionalities was prepared. It was found that the additional aromatic rings in the Cbz- and aromatic-containing ester moieties significantly improved the gelation properties of the resulting organogelators in aromatic solvents. Infrared and circular dichroism spectroscopy revealed that both H-bonding and pi-pi aromatic stacking interactions were the main driving forces for gelation. (c) 2006 Elsevier Ltd. All rights reserved.
• α-Galactose based neoglycopeptides. Inhibition of verotoxin binding to globotriosylceramide
  作者：Prabhat Arya、Kristina M.K. Kutterer、Huiping Qin、Johanne Roby、Michael L. Barnes、Shuqiong Lin、Clifford A. Lingwood、Markus G. Peter

  DOI：10.1016/s0968-0896(99)00226-6

  日期：1999.12

  Solution and solid phase strategies for the synthesis of a-galactose based neoglycopeptide derivatives 2-13 were developed. Neoglycopeptides generated were tested for the inhibition of verotoxin binding to globotriosylceramide (Gb3) using ELISA. Among all of the compounds tested, only the lipid derivatives of neoglycopeptides, 11, 12 and 13 were found to be inhibitors, IC50 = 2.0 mM (11b and 12c) and 0.2 mM (11c and 13c). All of the inhibitors (11b, 11c, 12c and 13c) have a similar branching of the two alpha-galactosyl units at the N-terminal glycine residue of a short peptide and a lipid moiety attached at the C-terminal site. Both of these factors seem to be crucial for the inhibition. It is interesting to note that the inhibitors have only a portion of the natural trisaccharide ligand. The secondary groups either may contribute in sub-site oriented interactions with the protein receptors or may mimic the internal sugar units of the cell-surface ligand, Gb3. (C) 1999 Elsevier Science Ltd. All rights reserved.