tert-butyl (1S,4S)-5-[(1S,3R)-3-[[(3S,4S)-3-methoxyoxan-4-yl]-(2,2,2-trifluoroacetyl)amino]-1-propan-2-ylcyclopentanecarbonyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate | 1294006-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl (1S,4S)-5-[(1S,3R)-3-[[(3S,4S)-3-methoxyoxan-4-yl]-(2,2,2-trifluoroacetyl)amino]-1-propan-2-ylcyclopentanecarbonyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
• CAS: 1294006-39-5
• 化学式: C₂₇H₄₂F₃N₃O₆
• 分子量: 561.642
• InChiKey: XCNWWKNJEZUEHA-ZBIJSRSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,4S)-5-[(1S,3R)-3-[[(3S,4S)-3-methoxyoxan-4-yl]-(2,2,2-trifluoroacetyl)amino]-1-propan-2-ylcyclopentanecarbonyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Design and synthesis of novel CCR2 antagonists: Investigation of non-aryl/heteroaryl binding motifs

  摘要：

  This report describes the design and synthesis of a series of CCR2 antagonists incorporating novel non-aryl/heteroaryl RHS (right hand side) motifs. Previous SAR in the area has suggested an aryl/heteroaryl substituent as a necessary structural feature for binding to the CCR2 receptor. Herein we describe the SAR with regards to potency (binding to hCCR2), dofetilide activity and metabolic stability (in vitro HLM) for this series. The resulting outcome was the identification of compounds with excellent properties for the investigation of the role of CCR2 in disease. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.052
• 作为产物：
  描述：

  (1S,4S)-4-(2,5-二甲基-1H-吡咯-1-基)-1-异丙基-2-环戊烯羧酸 在 platinum on activated charcoal 、 氢气 、 羟胺 、 三乙酰氧基硼氢化钠 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl (1S,4S)-5-[(1S,3R)-3-[[(3S,4S)-3-methoxyoxan-4-yl]-(2,2,2-trifluoroacetyl)amino]-1-propan-2-ylcyclopentanecarbonyl]-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  Design and synthesis of novel CCR2 antagonists: Investigation of non-aryl/heteroaryl binding motifs

  摘要：

  This report describes the design and synthesis of a series of CCR2 antagonists incorporating novel non-aryl/heteroaryl RHS (right hand side) motifs. Previous SAR in the area has suggested an aryl/heteroaryl substituent as a necessary structural feature for binding to the CCR2 receptor. Herein we describe the SAR with regards to potency (binding to hCCR2), dofetilide activity and metabolic stability (in vitro HLM) for this series. The resulting outcome was the identification of compounds with excellent properties for the investigation of the role of CCR2 in disease. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.052

文献信息

• 3-Aminocyclopentanecarboxamides as chemokine receptor modulators
  申请人：Pfizer Inc.

  公开号：EP2370442B9

  公开（公告）日：2013-09-04
• Design and synthesis of novel CCR2 antagonists: Investigation of non-aryl/heteroaryl binding motifs
  作者：John I. Trujillo、Wei Huang、Robert O. Hughes、D. Joseph Rogier、Steven R. Turner、Rajesh Devraj、Philip A. Morton、Chu-Biao Xue、Ganfeng Chao、Maryanne B. Covington、Robert C. Newton、Brian Metcalf

  DOI：10.1016/j.bmcl.2011.01.052

  日期：2011.3

  This report describes the design and synthesis of a series of CCR2 antagonists incorporating novel non-aryl/heteroaryl RHS (right hand side) motifs. Previous SAR in the area has suggested an aryl/heteroaryl substituent as a necessary structural feature for binding to the CCR2 receptor. Herein we describe the SAR with regards to potency (binding to hCCR2), dofetilide activity and metabolic stability (in vitro HLM) for this series. The resulting outcome was the identification of compounds with excellent properties for the investigation of the role of CCR2 in disease. (C) 2011 Elsevier Ltd. All rights reserved.