N-[2-[[(2S,3S)-1-[(2,4-dimethylphenyl)methylamino]-3-hydroxyheptan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide | 1374959-80-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-[[(2S,3S)-1-[(2,4-dimethylphenyl)methylamino]-3-hydroxyheptan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide
• CAS: 1374959-80-4
• 化学式: C₂₆H₃₄F₃N₃O₃
• 分子量: 493.569
• InChiKey: YDCZGNDUNVJAGP-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  90.5
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  间三氟甲基马尿酸 在 5%-palladium/activated carbon 、 氢气 、 sodium cyanoborohydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[2-[[(2S,3R)-1-[(2,4-dimethylphenyl)methylamino]-3-hydroxyheptan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide 、 N-[2-[[(2S,3S)-1-[(2,4-dimethylphenyl)methylamino]-3-hydroxyheptan-2-yl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Discovery of an orally-bioavailable CC Chemokine Receptor 2 antagonist derived from an acyclic diaminoalcohol backbone

  摘要：

  We describe an isostere-driven approach to improve upon a previously-described series of capped dipeptide antagonists of CC Chemokine Receptor 2 (CCR2). Modification of the substitution around the isostere was combined with additional changes in a distal aromatic substituent to provide single-digit nanomolar antagonists of CCR2. These studies led to the identification of 18, a compound that was suitable for studies in murine models of CCR2 activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.007

文献信息

• Discovery of an orally-bioavailable CC Chemokine Receptor 2 antagonist derived from an acyclic diaminoalcohol backbone
  作者：Percy H. Carter、Gregory D. Brown、Sarah R. King、Matthew E. Voss、Andrew J. Tebben、Robert J. Cherney、Sandhya Mandlekar、Yvonne C. Lo、Gengjie Yang、Persymphonie B. Miller、Peggy A. Scherle、Qihong Zhao、Carl P. Decicco

  DOI：10.1016/j.bmcl.2012.03.007

  日期：2012.5

  We describe an isostere-driven approach to improve upon a previously-described series of capped dipeptide antagonists of CC Chemokine Receptor 2 (CCR2). Modification of the substitution around the isostere was combined with additional changes in a distal aromatic substituent to provide single-digit nanomolar antagonists of CCR2. These studies led to the identification of 18, a compound that was suitable for studies in murine models of CCR2 activity. (C) 2012 Elsevier Ltd. All rights reserved.