5-(4-ethylphenyl)-N-methyl-N-((S)-1-((R)-3-(methylamino)pyrrolidine-1-carbonyl)pyrrolidin-3-yl)thiophene-2-carboxamide | 764721-69-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 5-(4-ethylphenyl)-N-methyl-N-((S)-1-((R)-3-(methylamino)pyrrolidine-1-carbonyl)pyrrolidin-3-yl)thiophene-2-carboxamide
• 英文别名: 5-(4-ethylphenyl)-N-methyl-N-[(3S)-1-[(3R)-3-(methylamino)pyrrolidine-1-carbonyl]pyrrolidin-3-yl]thiophene-2-carboxamide
• CAS: 764721-69-9
• 化学式: C₂₄H₃₂N₄O₂S
• 分子量: 440.61
• InChiKey: SZQMWBHNRRWIFS-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-ethylphenyl)-N-methyl-N-((S)-1-((R)-3-(methylamino)pyrrolidine-1-carbonyl)pyrrolidin-3-yl)thiophene-2-carboxamide 、 四氢吡喃酮 在 三乙酰氧基硼氢化钠 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 5-(4-ethylphenyl)-N-methyl-N-((S)-1-((R)-3-(methyl(tetrahydro-2H-pyran-4-yl)amino)pyrrolidine-1-carbonyl)pyrrolidin-3-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of retro bis-aminopyrrolidine urea (rAPU) derived small-molecule antagonists of the melanin-concentrating hormone receptor-1 (MCH-R1). Part 2

  摘要：

  The design, synthesis, and SAR of a series of retro bis-aminopyrrolidine ureas are described. Compounds from this series exhibited considerable binding affinity (K-i = 1 nM) and functional activity at MCH-R1, acceptable CYP2D6 inhibition, and good rat brain exposure. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.049
• 作为产物：
  描述：

  (S)-3-(tert-Butoxycarbonyl-methyl-amino)-pyrrolidine-1-carboxylic acid 4-nitro-phenyl ester 在 TEA 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.5h， 生成 5-(4-ethylphenyl)-N-methyl-N-((S)-1-((R)-3-(methylamino)pyrrolidine-1-carbonyl)pyrrolidin-3-yl)thiophene-2-carboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of retro bis-aminopyrrolidine urea (rAPU) derived small-molecule antagonists of the melanin-concentrating hormone receptor-1 (MCH-R1). Part 2

  摘要：

  The design, synthesis, and SAR of a series of retro bis-aminopyrrolidine ureas are described. Compounds from this series exhibited considerable binding affinity (K-i = 1 nM) and functional activity at MCH-R1, acceptable CYP2D6 inhibition, and good rat brain exposure. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.049

文献信息

• Synthesis and structure–activity relationships of retro bis-aminopyrrolidine urea (rAPU) derived small-molecule antagonists of the melanin-concentrating hormone receptor-1 (MCH-R1). Part 2
  作者：Sarah Hudson、Mehrak Kiankarimi、Martin W. Rowbottom、Troy D. Vickers、Dongpei Wu、Joseph Pontillo、Brett Ching、Wesley Dwight、Val S. Goodfellow、David Schwarz、Christopher E. Heise、Ajay Madan、Jenny Wen、William Ban、Hua Wang、Warren S. Wade

  DOI：10.1016/j.bmcl.2006.06.049

  日期：2006.9

  The design, synthesis, and SAR of a series of retro bis-aminopyrrolidine ureas are described. Compounds from this series exhibited considerable binding affinity (K-i = 1 nM) and functional activity at MCH-R1, acceptable CYP2D6 inhibition, and good rat brain exposure. (c) 2006 Elsevier Ltd. All rights reserved.