(2S,3S)-2-(3-((1H-imidazol-1-yl)methyl)benzamido)-3-methylpentanoic acid trifluoroacetic acid | 1536466-58-6

• 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: (2S,3S)-2-(3-((1H-imidazol-1-yl)methyl)benzamido)-3-methylpentanoic acid trifluoroacetic acid
• 英文别名: (2S,3S)-2-[[3-(imidazol-1-ylmethyl)benzoyl]amino]-3-methylpentanoic acid;2,2,2-trifluoroacetic acid
• CAS: 1536466-58-6
• 化学式: C₂HF₃O₂*C₁₇H₂₁N₃O₃
• 分子量: 429.396
• InChiKey: BOYIVLXPCGYZJG-NXCSSKFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  121.52
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(3-((1H-imidazol-1-yl)methyl)benzamido)-3-methylpentanoic acid trifluoroacetic acid 在 N-甲基吗啉 、 羟胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 15.17h， 以16%的产率得到3-((1H-imidazol-1-yl)methyl)-N-((2S,3S)-1-(hydroxyamino)-3-methyl-1-oxopentan-2-yl)benzamide
  参考文献：
  名称：

  Synthesis and evaluation of isoleucine derived angiotensin II AT2 receptor ligands

  摘要：

  Sixteen new C-terminally modified analogues of 2, a previously described potent and selective AT(2)R ligand, were designed, synthesized and evaluated for their affinity to the AT(2)R receptor. The introduction of large, hydrophobic substituents was shown to be beneficial and the most active compound (17, K-i = 8.5 mu M) was over 12-times more potent than the lead compound 2. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.12.040
• 作为产物：
  描述：

  3-羟甲基苯甲酸甲酯 在 N-甲基吗啉 、 三溴化磷 、 1-羟基苯并三唑 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.5h， 生成 (2S,3S)-2-(3-((1H-imidazol-1-yl)methyl)benzamido)-3-methylpentanoic acid trifluoroacetic acid
  参考文献：
  名称：

  Synthesis and evaluation of isoleucine derived angiotensin II AT2 receptor ligands

  摘要：

  Sixteen new C-terminally modified analogues of 2, a previously described potent and selective AT(2)R ligand, were designed, synthesized and evaluated for their affinity to the AT(2)R receptor. The introduction of large, hydrophobic substituents was shown to be beneficial and the most active compound (17, K-i = 8.5 mu M) was over 12-times more potent than the lead compound 2. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.12.040

文献信息

• Synthesis and evaluation of isoleucine derived angiotensin II AT2 receptor ligands
  作者：Jean-Baptiste Veron、Advait Joshi、Charlotta Wallinder、Mats Larhed、Luke R. Odell

  DOI：10.1016/j.bmcl.2013.12.040

  日期：2014.1

  Sixteen new C-terminally modified analogues of 2, a previously described potent and selective AT(2)R ligand, were designed, synthesized and evaluated for their affinity to the AT(2)R receptor. The introduction of large, hydrophobic substituents was shown to be beneficial and the most active compound (17, K-i = 8.5 mu M) was over 12-times more potent than the lead compound 2. (C) 2014 Published by Elsevier Ltd.