2-[4-(2,2,2-Trifluoro-acetylamino)-piperidine-1-carbonyl]-9H-xanthene-9-carboxylic acid tert-butyl ester | 438559-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-[4-(2,2,2-Trifluoro-acetylamino)-piperidine-1-carbonyl]-9H-xanthene-9-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-[4-[(2,2,2-trifluoroacetyl)amino]piperidine-1-carbonyl]-9H-xanthene-9-carboxylate
• CAS: 438559-71-8
• 化学式: C₂₆H₂₇F₃N₂O₅
• 分子量: 504.506
• InChiKey: DDJAMKIRFMLAFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[4-(2,2,2-Trifluoro-acetylamino)-piperidine-1-carbonyl]-9H-xanthene-9-carboxylic acid tert-butyl ester 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[4-(2,2,2-Trifluoro-acetylamino)-piperidine-1-carbonyl]-9H-xanthene-9-carboxylic acid [1-((E)-1-cyclonon-1-enyl)methyl-piperidin-4-yl]-amide
  参考文献：
  名称：

  Structure–activity relationships of xanthene carboxamides, novel CCR1 receptor antagonists

  摘要：

  The structure-activity relationships of xanthene carboxamide derivatives on the CCR1 receptor binding affinity and the functional antagonist activity were described. Previously, we reported a quaternarized xanthen-9-carboxamide I as a potent human CCR1 receptor antagonist that was derived from a xanthen-9-carboxamide lead 2a. Further derivatization of 2a focusing on installing an additional substituent into the xanthene ring resulted in the identification of 2b-1 with IC50 values of 1.8 nM and 13 nM in the binding assay using human CCRI receptors transfected CHO cells and in the functional assay using U937 cells expressing human CCRI receptors, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00559-x
• 作为产物：
  描述：

  2,7-dibromoxanthene-9-carboxylic acid 在 palladium on activated charcoal 正丁基锂 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 26.5h， 生成 2-[4-(2,2,2-Trifluoro-acetylamino)-piperidine-1-carbonyl]-9H-xanthene-9-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Structure–activity relationships of xanthene carboxamides, novel CCR1 receptor antagonists

  摘要：

  The structure-activity relationships of xanthene carboxamide derivatives on the CCR1 receptor binding affinity and the functional antagonist activity were described. Previously, we reported a quaternarized xanthen-9-carboxamide I as a potent human CCR1 receptor antagonist that was derived from a xanthen-9-carboxamide lead 2a. Further derivatization of 2a focusing on installing an additional substituent into the xanthene ring resulted in the identification of 2b-1 with IC50 values of 1.8 nM and 13 nM in the binding assay using human CCRI receptors transfected CHO cells and in the functional assay using U937 cells expressing human CCRI receptors, respectively. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00559-x