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

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(RS)-amino-5-phenylpentanoic acid ethyl ester hydrochloride
• 英文别名: (D)-2-Amino-5-phenylpentanoic Acid, Ethyl Ester Hydrochloride；2-amino-5-phenylpentanoic acid,ethyl ester hydrochloride；Ethyl 2-amino-5-phenylpentanoate HCl；ethyl 2-amino-5-phenylpentanoate;hydrochloride
• 化学式: C₁₃H₁₉NO₂*ClH
• 分子量: 257.76
• InChiKey: WOOKDZRTHXBTJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(RS)-amino-5-phenylpentanoic acid ethyl ester hydrochloride 在 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 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 1.0h， 生成 2-(RS)-amino-5-phenylpentanoic acid ethyl ester 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

• Treatment of congestive heart failure with growth hormone secretagogues
  申请人：Eli Lilly and Company

  公开号：US06329342B1

  公开（公告）日：2001-12-11

  The present invention is directed to methods for the modulation of cardiac function which comprise the administration of certain compounds, as defined herein, having growth hormone secretagogue activity.

  本发明涉及一种调节心脏功能的方法，该方法包括给予具有生长激素分泌素活性的特定化合物的管理，如本文所定义。
• INDOLYL GROUP CONTAINING COMPOUNDS AND THE USE THEREOF TO PROMOTE THE RELEASE OF GROWTH HORMONE(S)
  申请人：Merck & Co., Inc.

  公开号：EP0730578A1

  公开（公告）日：1996-09-11
• EP0730578A4
  申请人：——

  公开号：EP0730578A4

  公开（公告）日：1997-10-08
• US5663171A
  申请人：——

  公开号：US5663171A

  公开（公告）日：1997-09-02
• US6121325A
  申请人：——

  公开号：US6121325A

  公开（公告）日：2000-09-19