(1S,2S)-2-((S)-1-(((R)-tert-butylsulfinyl)amino)-3-phenylpropyl)-1-(3-(methoxymethoxy)propyl)-N-(2-(naphthalen-2-yl)ethyl)cyclopropane-1-carboxamide | 1428427-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2S)-2-((S)-1-(((R)-tert-butylsulfinyl)amino)-3-phenylpropyl)-1-(3-(methoxymethoxy)propyl)-N-(2-(naphthalen-2-yl)ethyl)cyclopropane-1-carboxamide
• CAS: 1428427-84-2
• 化学式: C₃₄H₄₆N₂O₄S
• 分子量: 578.816
• InChiKey: JAJZLXNUDRBMIP-MHAMIHRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.96
• 重原子数：
  41.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-2-((S)-1-(((R)-tert-butylsulfinyl)amino)-3-phenylpropyl)-1-(3-(methoxymethoxy)propyl)-N-(2-(naphthalen-2-yl)ethyl)cyclopropane-1-carboxamide 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.25h， 生成
  参考文献：
  名称：

  Three-Dimensional Structural Diversity-Oriented Peptidomimetics Based on the Cyclopropylic Strain

  摘要：

  Conformationally restricted peptidomimetics comprising eight stereoisomeric scaffolds with three-dimensional structural diversity were designed based on the structural features of cyclopropane, that is, cyclopropylic strain, which mimic wide-ranging tetrapeptide conformations covering beta-turns through beta-strands. Stereoselective synthesis of the designed peptidomimetics led to the identification of nonpeptidic melanocortin-4 receptor ligands.

  DOI：

  10.1021/ol400469w
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 戴斯-马丁氧化剂 、 copper(II) sulfate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯苯 、 异丙醇 、 甲苯 为溶剂， 反应 67.0h， 生成 (1S,2S)-2-((S)-1-(((R)-tert-butylsulfinyl)amino)-3-phenylpropyl)-1-(3-(methoxymethoxy)propyl)-N-(2-(naphthalen-2-yl)ethyl)cyclopropane-1-carboxamide
  参考文献：
  名称：

  Three-Dimensional Structural Diversity-Oriented Peptidomimetics Based on the Cyclopropylic Strain

  摘要：

  Conformationally restricted peptidomimetics comprising eight stereoisomeric scaffolds with three-dimensional structural diversity were designed based on the structural features of cyclopropane, that is, cyclopropylic strain, which mimic wide-ranging tetrapeptide conformations covering beta-turns through beta-strands. Stereoselective synthesis of the designed peptidomimetics led to the identification of nonpeptidic melanocortin-4 receptor ligands.

  DOI：

  10.1021/ol400469w

文献信息

• Cyclopropane-Based Peptidomimetics Mimicking Wide-Ranging Secondary Structures of Peptides: Conformational Analysis and Their Use in Rational Ligand Optimization
  作者：Akira Mizuno、Tomoshi Kameda、Tomoki Kuwahara、Hideyuki Endoh、Yoshihiko Ito、Shizuo Yamada、Kimiko Hasegawa、Akihito Yamano、Mizuki Watanabe、Mitsuhiro Arisawa、Satoshi Shuto

  DOI：10.1002/chem.201605312

  日期：2017.3.2

  chemical space filled by peptide secondary structures in terms of both main‐chain and side‐chain conformations. Based on these analyses, a lead stereoisomer targeting melanocortin receptors was identified, and its potency and subtype selectivity were improved by further derivatization. The presented strategy is effective not only for designing non‐peptidic ligands from a peptide ligand but also for the

  描述了我们先前报道的基于环丙烷的拟肽的详细构象分析和构象分析驱动的配体优化。计算结果和X射线晶体学分析表明，环丙烷的特征有效地以三维方式限制了分子的构象。随后的主成分分析表明，就主链和侧链构象而言，多样性涵盖了由肽二级结构填充的广阔化学空间。基于这些分析，确定了针对黑皮质素受体的先导立体异构体，并通过进一步衍生化提高了其效价和亚型选择性。