N-(((1-methylcyclohexyl)amino)carbonyl)leucine | 168471-10-1

• 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: N-(((1-methylcyclohexyl)amino)carbonyl)leucine
• 英文别名: (2S)-4-methyl-2-[(1-methylcyclohexyl)carbamoylamino]pentanoic acid
• CAS: 168471-10-1
• 化学式: C₁₄H₂₆N₂O₃
• mdl: MFCD15434517
• 分子量: 270.372
• InChiKey: FPAUAPABTIGHMF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(((1-methylcyclohexyl)amino)carbonyl)leucine 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-Methyl-2-((R)-2-(1-methyl-1H-indol-3-yl)-1-{(S)-4-methyl-2-[3-(1-methyl-cyclohexyl)-ureido]-pentanoylamino}-ethyl)-oxazole-4-carboxylic acid
  参考文献：
  名称：

  Azole Endothelin Antagonists. 2. Structure−Activity Studies

  摘要：

  Structure-activity studies have been performed in an attempt to improve the potency of a novel series of azole-based endothelin-A (ET(A)) selective antagonists. Modifications of the hydrophobic group on the terminal urea produced substantial effects on receptor affinity; in particular, the choice of cyclohexyl- or arylureas led to substantial improvements in activity. Conformational restriction of these groups provides an additional benefit. N-Methylation of the indole moiety which is part of the heterocyclic dipeptide surrogate also improves potency. The effects of these two modifications appear to be synergistic, with the best of the resultant doubly modified analogs (e.g. 14q, 15y, and 15ff) exhibiting an 80-200-fold improvement over the original leads.

  DOI：

  10.1021/jm950592+
• 作为产物：
  描述：

  L-亮氨酸苄酯对甲苯磺酸盐 在 palladium on activated charcoal N-甲基吗啉 、 叠氮磷酸二苯酯 、 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-(((1-methylcyclohexyl)amino)carbonyl)leucine
  参考文献：
  名称：

  Azole Endothelin Antagonists. 2. Structure−Activity Studies

  摘要：

  Structure-activity studies have been performed in an attempt to improve the potency of a novel series of azole-based endothelin-A (ET(A)) selective antagonists. Modifications of the hydrophobic group on the terminal urea produced substantial effects on receptor affinity; in particular, the choice of cyclohexyl- or arylureas led to substantial improvements in activity. Conformational restriction of these groups provides an additional benefit. N-Methylation of the indole moiety which is part of the heterocyclic dipeptide surrogate also improves potency. The effects of these two modifications appear to be synergistic, with the best of the resultant doubly modified analogs (e.g. 14q, 15y, and 15ff) exhibiting an 80-200-fold improvement over the original leads.

  DOI：

  10.1021/jm950592+

文献信息

• Azole Endothelin Antagonists. 2. Structure−Activity Studies
  作者：Thomas W. von Geldern、Jeffrey A. Kester、Radhika Bal、Jinshyun R. Wu-Wong、William Chiou、Douglas B. Dixon、Terry J. Opgenorth

  DOI：10.1021/jm950592+

  日期：1996.1.1

  Structure-activity studies have been performed in an attempt to improve the potency of a novel series of azole-based endothelin-A (ET(A)) selective antagonists. Modifications of the hydrophobic group on the terminal urea produced substantial effects on receptor affinity; in particular, the choice of cyclohexyl- or arylureas led to substantial improvements in activity. Conformational restriction of these groups provides an additional benefit. N-Methylation of the indole moiety which is part of the heterocyclic dipeptide surrogate also improves potency. The effects of these two modifications appear to be synergistic, with the best of the resultant doubly modified analogs (e.g. 14q, 15y, and 15ff) exhibiting an 80-200-fold improvement over the original leads.