(S)-2-Bromo-3-(1H-indol-3-yl)propanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-Bromo-3-(1H-indol-3-yl)propanoic acid
• 英文别名: (2S)-2-bromo-3-(1H-indol-3-yl)propanoic acid
• 化学式: C₁₁H₁₀BrNO₂
• 分子量: 268.11
• InChiKey: GZDAPFIVWAXKPD-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D-赖氨酸 、 2-苯乙胺 、 2-benzothiazolyl 2-methanesulfonoxyethyl disulfide 、 (S)-2-Bromo-3-(1H-indol-3-yl)propanoic acid 以74%的产率得到(2S,5R)-5-(4-Amino-butyl)-2-(1H-indol-3-ylmethyl)-7-phenethyl-[1,4,7]thiadiazonane-3,6-dione
  参考文献：
  名称：

  Compounds That Activate the Mouse Melanocortin-1 Receptor Identified by Screening a Small Molecule Library Based upon the β-Turn

  摘要：

  A library of 951 compounds based upon the beta-turn motif were examined for their ability to stimulate the melanocortin-1 receptor. From this screening process, we have identified two compounds possessing low micromolar agonist activity at the mMC1R. The compound EL1 with racemic Nal(2') in the i + 1 position, DPro in the i + 2 position, and Trp in the i + 3 position possesses an EC50 Of 42.5 +/- 6.9 mu M. Compound EL2 with Trp in the i + 1 position, DLys in the i + 2 position, and Phe in the i + 3 position possesses an EC50 value of 63.4 +/- 26.9 mu M. The results of the library screening process are consistent with a hypothesis dating back to the 1980s proposing that a beta-turn conformation involving the melanocortin "Phe-Arg-Trp" core amino acids provides the key recognition element. Additionally, these compounds represent the first nonpeptidic heterocyclic molecules reported to date that are able to activate the MC1R, a melanocyte receptor involved in skin pigmentation and animal coat coloration.

  DOI：

  10.1021/jm990190s

文献信息

• Identification of a Potent Heterocyclic Ligand To Somatostatin Receptor Subtype 5 by the Synthesis and Screening of β-Turn Mimetic Libraries
  作者：Andrew J. Souers、Alex A. Virgilio、Åsa Rosenquist、Wasyl Fenuik、Jonathan A. Ellman

  DOI：10.1021/ja983742p

  日期：1999.3.1

  Methods for the parallel synthesis of medium-ring heterocyclic β-turn mimetics (1) are described, which enable the rapid preparation of libraries of mimetics for the identification of small molecule ligands to receptors. The generality of this method was first demonstrated by the rapid and high-yielding synthesis of mimetics 1a−g that display a wide range of proteinogenic amino acid side chains. Small

  描述了平行合成中环杂环 β-转角模拟物 (1) 的方法，它能够快速制备模拟物库，用于识别受体的小分子配体。这种方法的通用性首先通过模拟物 1a-g 的快速和高产合成来证明，该模拟物显示出广泛的蛋白质氨基酸侧链。然后通过基于在生长抑素转角区域中发现的关键 Trp-Lys 基序合成一个聚焦的 β-转角模拟物库来鉴定具有药用价值的肽生长抑素的小分子杂环模拟物。针对一组五种克隆的人类生长抑素受体 (hSST1-hSST5) 筛选文库，鉴定出一种对 hSST5 具有选择性的有效小分子配体 (1h)，以及针对受体亚型 1-4 的有效配体。此外，结构-活性关系被用来确定三种多样性输入中每一种的重要性……