2-(Diethylcarbamoylamino)-5-(trifluoromethyl)benzoic acid | 1176145-48-4

• 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: 2-(Diethylcarbamoylamino)-5-(trifluoromethyl)benzoic acid
• CAS: 1176145-48-4
• 化学式: C₁₃H₁₅F₃N₂O₃
• 分子量: 304.269
• InChiKey: AWLALYAMGHYFBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(Diethylcarbamoylamino)-5-(trifluoromethyl)benzoic acid 、 在 (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 (+/-)2-{[(Diethylamino)carbonyl]amino}-N-(2-{[(1S*,2R*)-2-({[4-(methylthio)phenyl]sulfonyl}methyl)cyclohexyl]amino}-2-oxoethyl)-5-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Novel sulfone-containing di- and trisubstituted cyclohexanes as potent CC chemokine receptor 2 (CCR2) antagonists

  摘要：

  Potent sulfone-containing di- and trisubstituted cyclohexanes were synthesized and evaluated as CC chemokine receptor 2 (CCR2) antagonists. This led to the trisubstituted derivative 54, which exhibited excellent binding (CCR2 IC50 = 1.3 nM) and functional antagonism (calcium flux IC50 = 0.5 nM and chemotaxis IC50 = 0.2 nM). The superiority of the trisubstituted scaffold was rationalized to be the result of a conformational rigidification, which provided insight into the bioactive conformation of this chemotype. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.041
• 作为产物：
  描述：

  4-(tert-butyl)-1-(3-ethyl-2-methylenepentyl)-2-(hexa-1,5-dien-2-yl)benzene 在 四氢吡咯 、 四(三苯基膦)钯 作用下， 以 乙腈 为溶剂， 生成 2-(Diethylcarbamoylamino)-5-(trifluoromethyl)benzoic acid
  参考文献：
  名称：

  Novel sulfone-containing di- and trisubstituted cyclohexanes as potent CC chemokine receptor 2 (CCR2) antagonists

  摘要：

  Potent sulfone-containing di- and trisubstituted cyclohexanes were synthesized and evaluated as CC chemokine receptor 2 (CCR2) antagonists. This led to the trisubstituted derivative 54, which exhibited excellent binding (CCR2 IC50 = 1.3 nM) and functional antagonism (calcium flux IC50 = 0.5 nM and chemotaxis IC50 = 0.2 nM). The superiority of the trisubstituted scaffold was rationalized to be the result of a conformational rigidification, which provided insight into the bioactive conformation of this chemotype. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.041

文献信息

• Novel sulfone-containing di- and trisubstituted cyclohexanes as potent CC chemokine receptor 2 (CCR2) antagonists
  作者：Robert J. Cherney、Ruowei Mo、Dayton T. Meyer、Matthew E. Voss、Yvonne C. Lo、Gengjie Yang、Persymphonie B. Miller、Peggy A. Scherle、Andrew J. Tebben、Percy H. Carter、Carl P. Decicco

  DOI：10.1016/j.bmcl.2009.05.041

  日期：2009.7

  Potent sulfone-containing di- and trisubstituted cyclohexanes were synthesized and evaluated as CC chemokine receptor 2 (CCR2) antagonists. This led to the trisubstituted derivative 54, which exhibited excellent binding (CCR2 IC50 = 1.3 nM) and functional antagonism (calcium flux IC50 = 0.5 nM and chemotaxis IC50 = 0.2 nM). The superiority of the trisubstituted scaffold was rationalized to be the result of a conformational rigidification, which provided insight into the bioactive conformation of this chemotype. (C) 2009 Elsevier Ltd. All rights reserved.