3,3'-(dibenzo[b,d]furan-4,6-diyl)dipropanoic acid | 137959-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3,3'-(dibenzo[b,d]furan-4,6-diyl)dipropanoic acid
• 英文别名: 4,6-dibenzofuran-dipropionic acid；4,6-dibenzofuranbispropionic acid；4,6-Dibenzofurandipropionic acid；3-[6-(2-Carboxyethyl)dibenzofuran-4-yl]propanoic acid
• CAS: 137959-91-2
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: VMOREDRCSHIRTH-UHFFFAOYSA-N

物化性质

• 沸点：
  561.3±40.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3'-(dibenzo[b,d]furan-4,6-diyl)dipropanoic acid 在 3 A molecular sieve 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 反应 74.0h， 生成 ethyl 4-<2-<(tert-butyloxy)carbamyl>ethyl>-6-dibenzofuranpropionate
  参考文献：
  名称：

  Tsang, Kwok Yin; Diaz, Humberto; Graciani, Nilsa, Journal of the American Chemical Society, 1994, vol. 116, # 9, p. 3988 - 4005

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯并呋喃 在 palladium on activated charcoal palladium diacetate 、 sodium hydroxide 、 正丁基锂 、 氢气 、 一氯化碘 、 potassium carbonate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,3'-(dibenzo[b,d]furan-4,6-diyl)dipropanoic acid
  参考文献：
  名称：

  The synthesis of dibenzofuran based diacids and amino acids designed to nucleate parallel and antiparallel β-sheet formation.

  摘要：

  4-(N-tert-butyloxycarbonyl-2-aminoethyl-)-6-dibenzofuranpropionic acid (1) and 4,6-dibenzofurandipropionic acid (2) designed to nucleate antiparallel and parallel beta-sheet formation, respectively, have been synthesized in multi-gram quantities.

  DOI：

  10.1016/s0040-4039(00)93540-8

文献信息

• Transthyretin Stabilization
  申请人：Kelly Jeffery W.

  公开号：US20080319175A1

  公开（公告）日：2008-12-25

  Dibenzofuran-4,6-dicarboxylic acid core structures having an aromatic substituent appended onto the at the C1 position using three different types of linkages are disclosed herein and shown to afford exceptional amyloidogenesis inhibitors that display increased affinity and greatly increased binding selectivity to TTR over all the other plasma proteins, relative to lead compound 1. It is further disclosed herein that these compounds function by imposing kinetic stabilization on the TTR tetramer.

  本文披露了在Dibenzofuran-4,6-dicarboxylic acid核心结构上附加芳香基取代物的三种不同类型的连接方式，这些取代物被证明是出色的淀粉样生成抑制剂，相对于引领化合物1，它们显示出增加的亲和力和极大的选择性结合TTR而非其他所有血浆蛋白质。此外，本文还披露了这些化合物通过对TTR四聚体施加动力学稳定作用来发挥作用。
• The synthesis of dibenzofuran based diacids and amino acids designed to nucleate parallel and antiparallel β-sheet formation.
  作者：Humberto Diaz、Jeffery W. Kelly

  DOI：10.1016/s0040-4039(00)93540-8

  日期：1991.10

  4-(N-tert-butyloxycarbonyl-2-aminoethyl-)-6-dibenzofuranpropionic acid (1) and 4,6-dibenzofurandipropionic acid (2) designed to nucleate antiparallel and parallel beta-sheet formation, respectively, have been synthesized in multi-gram quantities.
• Design and Synthesis of Specific Probes for Human 5-HT₄ Receptor Dimerization Studies
  作者：Jean-Louis Soulier、Olivier Russo、Mireille Giner、Lucie Rivail、Magali Berthouze、Sandrine Ongeri、Bernard Maigret、Rodolphe Fischmeister、Frank Lezoualc'h、Sames Sicsic、Isabelle Berque-Bestel

  DOI：10.1021/jm050234z

  日期：2005.10.1

  Recently, human 5-HT4 receptors have been demonstrated to form constitutive dimers in living cells. To evaluate the role of dimerization on the 5-HT4 receptor function, we investigated the conception and the synthesis of bivalent molecules able to influence the dimerization process. Their conception is based on a model of the 5-HT4 receptor dimer derived from protein/protein docking experiments. These bivalent ligands are constituted by two ML10302 units, a specific 5-HT4 ligand, linked through a spacer of different sizes and natures. These synthesized bivalent ligands were evaluated in binding assays and cyclic AMP production on the 5-HT4(e/g) receptor isoform stably transfected in C6 glial cells. Our data showed that bivalent ligands conserved a similar affinity compared to the basal ML10302 unit. Nevertheless, according to the nature and the size of the spacer, the pharmacological profile of ML10302 is more or less conserved. In view of the interest of bivalent ligands for investigating the GPCR dimerization process, these 5-HT4 specific bivalent ligands constitute valuable pharmacological tools for the study of 5-HT4 receptor dimerization.
• The nucleation of monomeric parallel β-sheet-like structures and their self-assembly in aqueous solution
  作者：Penchit Chitnumsub、Wayne R. Fiori、Hilal A. Lashuel、Humberto Diaz、Jeffery W. Kelly

  DOI：10.1016/s0968-0896(98)00222-3

  日期：1999.1

  The aromatic diacid residue 4,6-dibenzofuranbispropionic acid (1) was designed to nucleate a parallel beta-sheet-like structure in small peptides in aqueous solution via a hydrogen-bonded hydrophobic cluster. Even though a 14-membered ring hydrogen bond necessary for parallel beta-sheet formation is favored in simple amides composed of 1, this hydrogen bonding interaction does not appear to be sufficient to nucleate parallel beta-sheet formation in the absence of hydrophobic clustering between the dibenzofuran portion of 1 and the hydrophobic side chains of the flanking alpha-amino acids. The subsequence --hydrophobic residue-1-hydrophobic residue-- is required for folding in the context of a nucleated two-stranded parallel beta-sheet structure. In all cases where the peptidomimetics can fold into two diastereomeric parallel beta-sheet structures having different hydrogen bonding networks, these conformations appear to exchange rapidly. The majority of the parallel beta-sheet structures evaluated herein undergo linked intramolecular folding and self-assembly, affording a fibrillar beta-sheet quaternary structure. To unlink folding and assembly, asymmetric parallel beta-sheet structures incorporating N-methylated alpha-amino acid residues have been synthesized using a new solid phase approach. Residue 1 facilitates the folding of several peptides described within affording a monomeric parallel beta-sheet-like structure in aqueous solution, as ascertained by a variety of spectroscopic and biophysical methods, increasing our understanding of parallel beta-sheet structure.
• Tsang, Kwok Yin; Diaz, Humberto; Graciani, Nilsa, Journal of the American Chemical Society, 1994, vol. 116, # 9, p. 3988 - 4005
  作者：Tsang, Kwok Yin、Diaz, Humberto、Graciani, Nilsa、Kelly, Jeffery W.

  DOI：——

  日期：——