N-(((9H-氟-9-基)甲氧基)羰基)-N-苄基丙氨酸 | 540483-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-(((9H-氟-9-基)甲氧基)羰基)-N-苄基丙氨酸
• 英文名称: 2-{benzyl-[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propionic acid
• 英文别名: N-(((9H-Fluoren-9-yl)methoxy)carbonyl)-N-benzylalanine；2-[benzyl(9H-fluoren-9-ylmethoxycarbonyl)amino]propanoic acid
• CAS: 540483-59-8
• 化学式: C₂₅H₂₃NO₄
• 分子量: 401.462
• InChiKey: QFVKHZGPQOFFBR-UHFFFAOYSA-N

物化性质

• 沸点：
  605.9±44.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(((9H-氟-9-基)甲氧基)羰基)-N-苄基丙氨酸 、 tert-butyl-3-{(2R)-2-amino-2-[1-(2-phenylethyl)carbamoyl]ethyl}-1H-1-indolecarboxylate 以73%的产率得到2-Benzylamino-N-[(R)-2-(1H-indol-3-yl)-1-phenethylcarbamoyl-ethyl]-propionamide
  参考文献：
  名称：

  Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3

  摘要：

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

  DOI：

  10.1021/jm0210921
• 作为产物：
  描述：

  氯甲酸-9-芴基甲酯 、 2-N-苄基氨基丙酸 在 碳酸氢钠 作用下， 以 1,4-二氧六环 为溶剂， 以1.26 g的产率得到N-(((9H-氟-9-基)甲氧基)羰基)-N-苄基丙氨酸
  参考文献：
  名称：

  Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3

  摘要：

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.

  DOI：

  10.1021/jm0210921

文献信息

• Cyclic Peptoids as Topological Templates: Synthesis via Central to Conformational Chirality Induction
  作者：Assunta D’Amato、Giovanni Pierri、Chiara Costabile、Giorgio Della Sala、Consiglia Tedesco、Irene Izzo、Francesco De Riccardis

  DOI：10.1021/acs.orglett.7b03786

  日期：2018.2.2

  the synthesis of diastereopure cyclic peptoids containing an N-benzyl alanine residue. Molecular modeling, NMR spectroscopy, single-crystal X-ray diffraction studies, and HPLC with chiral stationary phase demonstrated easy formation of free and sodium/benzylammonium complexed cyclic oligomers through strategic incorporation of a single stereogenic center in the oligomeric backbone. The synthesis of

  手性诱导用于合成含有N-苄基丙氨酸残基的非对映体环状拟肽。分子建模，NMR光谱学，单晶X射线衍射研究和具有手性固定相的HPLC表明，通过在寡聚主链中策略性地并入单个立体生成中心，可以轻松形成游离的钠盐和苄基铵络合的环状低聚物。现在可以合成具有确定的构象手性和合适的侧链拓扑的环状类肽。
• Design of Selective Peptidomimetic Agonists for the Human Orphan Receptor BRS-3
  作者：Dirk Weber、Claudia Berger、Peter Eickelmann、Jochen Antel、Horst Kessler

  DOI：10.1021/jm0210921

  日期：2003.5.1

  New tool substances may help to unravel the physiological role of the human orphan receptor BRS-3 and its possible use as a drug target for the treatment of obesity and cancer. In continuation of our work on BRS-3, the solid- and solution-phase synthesis of a library of low molecular weight peptidomimetic agonists based on the recently developed short peptide agonist 4 is described. Functional potencies of the compounds were determined measuring calcium mobilization in a fluorometric imaging plate reader (FLIPR) assay. Focusing on the N-terminus, the D-Phe-Gln moiety of 4 was modified in a combinatorial. SAR-oriented medicinal chemistry approach. With the incorporation of N-arylated glycine and alanine building blocks azaglycine, piperazine, or piperidine and the synthesis of semicarbazides and semicarbazones, a number of highly potent and selective compounds with a reduced number of peptide bonds were obtained, which also should have enhanced metabolic stability.