(S)-2-Cyclopropylmethyl-pent-4-enoic acid 3,5-bis-trifluoromethyl-benzylamide | 909717-45-9

• 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: (S)-2-Cyclopropylmethyl-pent-4-enoic acid 3,5-bis-trifluoromethyl-benzylamide
• CAS: 909717-45-9
• 化学式: C₁₈H₁₉F₆NO
• 分子量: 379.345
• InChiKey: ZJYMJHZMQOWTJN-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1R,3'R)-3'-methylspiro[indene-1,4'-piperidine] 、 (S)-2-Cyclopropylmethyl-pent-4-enoic acid 3,5-bis-trifluoromethyl-benzylamide 在 臭氧 、 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 (2R)-N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-(cyclopropylmethyl)-4-[(1R,3'R)-3'-methylspiro[indene-1,4'-piperidine]-1'-yl]butanamide
  参考文献：
  名称：

  4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

  摘要：

  A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1'H-spiro[indene-1,4'-piperidin]-1'-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C-2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3'R)-3'-methyl-1'H-spiro[indene-1,4'-piperidin]-1'-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.011
• 作为产物：
  描述：

  3-(3-cyclopropyl-1-oxopropyl)-4(S)-phenylmethyl-2-oxazolidinone 在 N-羟基-7-氮杂苯并三氮唑 、 过氧化氢,锂盐(1:1) 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-2-Cyclopropylmethyl-pent-4-enoic acid 3,5-bis-trifluoromethyl-benzylamide
  参考文献：
  名称：

  4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

  摘要：

  A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1'H-spiro[indene-1,4'-piperidin]-1'-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C-2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3'R)-3'-methyl-1'H-spiro[indene-1,4'-piperidin]-1'-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.011