4-(Fmoc-2-aminoethyl)-6-dibenzofuranpropionic acid | 172174-50-4

• 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: 4-(Fmoc-2-aminoethyl)-6-dibenzofuranpropionic acid
• 英文别名: 6-[2-[(9H-Fluoren-9-ylmethoxycarbonyl)amino]ethyl]dibenzofuran-4-propionic acid；3-[6-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]dibenzofuran-4-yl]propanoic acid
• CAS: 172174-50-4
• 化学式: C₃₂H₂₇NO₅
• 分子量: 505.57
• InChiKey: BUSYOHIPGRVZGT-UHFFFAOYSA-N

物化性质

• 沸点：
  749.6±60.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-叔丁氧基-2-氧代乙氧基)苯甲酸 、 Alpha-甲基-4-硝基苯乙酸 、 Fmoc-Lys(Dde)-OH 、 4-(Fmoc-2-aminoethyl)-6-dibenzofuranpropionic acid 生成 2-[3-[[(5S)-6-[2-[6-(3-amino-3-oxopropyl)dibenzofuran-4-yl]ethylamino]-5-[2-(4-nitrophenyl)propanoylamino]-6-oxohexyl]carbamoyl]phenoxy]acetic acid
  参考文献：
  名称：

  Aminodeoxychorismate Synthase Inhibitors from One-Bead One-Compound Combinatorial Libraries:  “Staged” Inhibitor Design

  摘要：

  4-Amino-4-deoxychorismate synthase (ADCS) catalyzes the first step in the conversion of chorismate into p-aminobenzoate, which is incorporated into folic acid. We aim to discover compounds that inhibit ADCS and serve as leads for a new class of antimicrobial compounds. This report presents (1) synthesis of a mass-tag encoded library based on a "staged" design, (2) massively parallel fluorescence-based on-bead screening, (3) rapid structural identification of hits, and (4) full kinetic analysis of ADCS. All inhibitors are competitive against chorismate and Mg2+. The most potent ADCS inhibitor identified has a K-i of 360 mu M. We show that the combinatorial diversity elements add substantial binding affinity by interacting with residues outside of but proximal to the active site. The methods presented here constitute a paradigm for inhibitor discovery through active site targeting, enabled by rapid library synthesis, facile massively parallel screening, and straightforward hit identification.

  DOI：

  10.1021/jm0609869
• 作为产物：
  描述：

  ethyl 4-<2-<(tert-butyloxy)carbamyl>ethyl>-6-dibenzofuranpropionate 在 盐酸 、 sodium carbonate 、 三氟乙酸 作用下， 以 溶剂黄146 为溶剂， 反应 24.83h， 生成 4-(Fmoc-2-aminoethyl)-6-dibenzofuranpropionic acid
  参考文献：
  名称：

  Improved Synthesis of the Boc and Fmoc Derivatives of 4-(2‘-Aminoethyl)-6-dibenzofuranpropionic Acid:  An Unnatural Amino Acid That Nucleates β-Sheet Folding

  摘要：

  DOI：

  10.1021/jo961063w

文献信息

• Inhibition of cell adhesion and immune responses in the mouse model of collagen-induced arthritis with a peptidomimetic that blocks CD2-CD58 interface interactions
  作者：Ameya S. Gokhale、Rushikesh Sable、Jason D. Walker、Leslie McLaughlin、Konstantin G. Kousoulas、Seetharama D. Jois

  DOI：10.1002/bip.22692

  日期：2015.11

  immunomodulation in the collagen‐induced arthritis (CIA) model. The ability of compound 7 to bind to CD58 protein was assessed using flow cytometry. The effect of compound 7 on modulating the immune response was evaluated in an autoimmune disease using CIA in mice. The stability of compound 7 was evaluated in mouse serum using mass spectrometry. Antibody (Ab) binding inhibition studies suggested that compound 7 binds

  CD2和CD58是两个重要的共刺激分子，参与产生正常免疫信号所需的信号II。但是，在自身免疫性疾病中发现异常免疫信号传导的情况下，这种相互作用可以作为有益的靶标。本研究的目的是基于CD2蛋白粘附域的β链结构设计一种拟肽（化合物7），以抑制CD2-CD58蛋白与蛋白质的相互作用及其对胶原性关节炎（CIA）免疫调节的影响）模型。使用流式细胞术评估化合物7结合CD58蛋白的能力。使用CIA在小鼠的自身免疫疾病中评估了化合物7对调节免疫应答的作用。使用质谱法评估化合物7在小鼠血清中的稳定性。抗体（Ab）结合抑制研究表明化合物7与CD58蛋白结合。复合与对照治疗相比，当在CIA小鼠模型中给药时7可以成功地调节免疫反应，并降低抗胶原Ab的水平并降低干扰素γ（IFN-γ）的水平。发现化合物7在小鼠血清中长达48小时无免疫原性并且稳定。结果表明，化合物7可以作为免疫调节的前导化合物，并且可以作为自身免疫性
• Medical uses of intercellular communication facilitating compounds
  申请人：Larsen Due Bjarne

  公开号：US20050113293A1

  公开（公告）日：2005-05-26

  Disclosed are novel peptides including antiarrhythmic peptides that have improved stability. Further disclosed are compositions that include such peptides and methods of using the compositions particularly as medicaments.

  本发明涉及新型肽，包括具有改善稳定性的抗心律失常肽。进一步揭示了包括这样的肽的组合物以及使用这些组合物作为药物的方法。
• Synthesis and Structural and Functional Evaluation of a Protein Modified with a β-Turn Mimic
  作者：Fabienne Jean、Eric Buisine、Oleg Melnyk、Hervé Drobecq、Benoît Odaert、Michel Hugues、Guy Lippens、André Tartar

  DOI：10.1021/ja972346o

  日期：1998.6.1

  Protein engineering has traditionally relied upon the possibility of changing the primary structure by either site-directed mutagenesis or peptide synthesis. Recently the scope of these methods has been extended to non-natural amino acids by both biosynthetic and synthetic approaches. A further step in which a complete structural motif is replaced by an equivalent synthetic mimic has been validated in small peptides. We extend these results to the field of protein engineering by incorporating a beta-turn mimic into a small protein, scyllatoxin, which contains all major secondary structure elements. The synthetic scyllatoxin was structurally and functionally characterized and Pound to be equivalent to the native protein.
• MEDICAL USES OF INTERCELLULAR COMMUNICATION FACILITATING COMPOUNDS
  申请人：Zealand Pharma A/S

  公开号：EP1370276A2

  公开（公告）日：2003-12-17
• US7339023B2
  申请人：——

  公开号：US7339023B2

  公开（公告）日：2008-03-04