2-(RS)-amino-5-phenylpentanoic acid hydrochloride

• 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: 2-(RS)-amino-5-phenylpentanoic acid hydrochloride
• 英文别名: (3-phenylpropyl)glycine-hydrochloride；2-Amino-5-phenylpentanoic acid hydrochloride；2-amino-5-phenylpentanoic acid;hydrochloride
• 化学式: C₁₁H₁₅NO₂*ClH
• 分子量: 229.707
• InChiKey: ZVIHANCVVAVMNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(RS)-amino-5-phenylpentanoic acid hydrochloride 在 吡啶 、 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 2-(RS)-{2-[(1H-indole-2-carbonyl)amino]benzoylamino}-5-phenylpentanoic acid ethyl ester
  参考文献：
  名称：

  New Anthranilic Acid Based Antagonists with High Affinity and Selectivity for the Human Cholecystokinin Receptor 1 (hCCK₁-R)

  摘要：

  The anthranilic acid diamides represent the most recent class of nonpeptide CCK1 receptor (CCK1-R) antagonists. Herein we describe the second phase of the anthranilic acid C-terminal optimization using nonproteinogenic amino acids containing a phenyl ring in their side chain. The Homo-Phe derivative 2 (VL-0797) enhanced 12-fold the affinity for the rat CCK1-R affinity and 15-fold for the human CCK1-R relative to the reference compound 12 (VL-0395). The eutomer of 2 (6) exhibited a nanomolar range affinity toward the human CCK1-R and was at least 400-fold selective for the CCK1-R over the CCK2-R. Molecular docking in the modeled CCK1-R and its validation by site-directed mutagenesis experiments showed that the 6 binding site overlaps that occupied by the C-terminal bioactive region of the natural agonist CCK. Owing to their interesting properties, new compounds provided by this study represent a solid basis for further advances aimed at synthesis of clinically valuable CCK1-R antagonists.

  DOI：

  10.1021/jm200438b
• 作为产物：
  描述：

  1-碘-3-苯基丙烷 在 盐酸 、 sodium ethanolate 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 2-(RS)-amino-5-phenylpentanoic acid hydrochloride
  参考文献：
  名称：

  New Anthranilic Acid Based Antagonists with High Affinity and Selectivity for the Human Cholecystokinin Receptor 1 (hCCK₁-R)

  摘要：

  The anthranilic acid diamides represent the most recent class of nonpeptide CCK1 receptor (CCK1-R) antagonists. Herein we describe the second phase of the anthranilic acid C-terminal optimization using nonproteinogenic amino acids containing a phenyl ring in their side chain. The Homo-Phe derivative 2 (VL-0797) enhanced 12-fold the affinity for the rat CCK1-R affinity and 15-fold for the human CCK1-R relative to the reference compound 12 (VL-0395). The eutomer of 2 (6) exhibited a nanomolar range affinity toward the human CCK1-R and was at least 400-fold selective for the CCK1-R over the CCK2-R. Molecular docking in the modeled CCK1-R and its validation by site-directed mutagenesis experiments showed that the 6 binding site overlaps that occupied by the C-terminal bioactive region of the natural agonist CCK. Owing to their interesting properties, new compounds provided by this study represent a solid basis for further advances aimed at synthesis of clinically valuable CCK1-R antagonists.

  DOI：

  10.1021/jm200438b

文献信息

• Synthesis and antitumor activity of platinum(II) complexes containing substituted ethylenediamine ligands
  作者：Henri Brunner、Peter Hankofer、Ulrich Holzinger、Barbara Treittinger、Helmut Schönenberger

  DOI：10.1016/0223-5234(90)90162-v

  日期：1990.2
• CYCLIC CARBAMATES AND ISOXAZOLIDINES AS IIB/IIIA ANTAGONISTS
  申请人：Du Pont Pharmaceuticals Company

  公开号：EP1091945A1

  公开（公告）日：2001-04-18
• [EN] CYCLIC CARBAMATES AND ISOXAZOLIDINES AS IIB/IIIA ANTAGONISTS<br/>[FR] ISOXAZOLIDINES ET CARBAMATES CYCLIQUES UTILISES COMME ANTAGONISTES DE IIB/IIIA
  申请人：DU PONT PHARM CO

  公开号：WO2000000481A1

  公开（公告）日：2000-01-06

  The present invention relates generally to cyclic carbamates and isoxazolidines of Formula (I) or their pharmaceutically acceptable salts thereof, which are useful as antagonists of the platelet glycoprotein IIb/IIIa fibrinogen receptor complex, to pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.
• New Anthranilic Acid Based Antagonists with High Affinity and Selectivity for the Human Cholecystokinin Receptor 1 (hCCK₁-R)
  作者：Michela V. Pavan、Lucia Lassiani、Federico Berti、Giorgio Stefancich、Alessia Ciogli、Francesco Gasparrini、Laura Mennuni、Flora Ferrari、Chantal Escrieut、Esther Marco、Francesco Makovec、Daniel Fourmy、Antonio Varnavas

  DOI：10.1021/jm200438b

  日期：2011.8.25

  The anthranilic acid diamides represent the most recent class of nonpeptide CCK1 receptor (CCK1-R) antagonists. Herein we describe the second phase of the anthranilic acid C-terminal optimization using nonproteinogenic amino acids containing a phenyl ring in their side chain. The Homo-Phe derivative 2 (VL-0797) enhanced 12-fold the affinity for the rat CCK1-R affinity and 15-fold for the human CCK1-R relative to the reference compound 12 (VL-0395). The eutomer of 2 (6) exhibited a nanomolar range affinity toward the human CCK1-R and was at least 400-fold selective for the CCK1-R over the CCK2-R. Molecular docking in the modeled CCK1-R and its validation by site-directed mutagenesis experiments showed that the 6 binding site overlaps that occupied by the C-terminal bioactive region of the natural agonist CCK. Owing to their interesting properties, new compounds provided by this study represent a solid basis for further advances aimed at synthesis of clinically valuable CCK1-R antagonists.