N-(benzoxazol-2-yl)-N-[1-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl)-piperidin-4-yl]amine | 824403-38-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(benzoxazol-2-yl)-N-[1-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl)-piperidin-4-yl]amine
• 英文别名: N-(1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-yl)benzo[d]oxazol-2-amine；N-[1-[[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]methyl]piperidin-4-yl]-1,3-benzoxazol-2-amine
• CAS: 824403-38-5
• 化学式: C₂₂H₂₉N₃O
• 分子量: 351.492
• InChiKey: QXQOSWMICBNZNQ-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  41.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(benzoxazol-2-yl)-N-[1-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl)-piperidin-4-yl]amine 、 碘甲烷 以 乙醚 为溶剂， 生成 4-(benzoxazol-2-ylamino)-1-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-ylmethyl)-1-methylpiperidinium iodide
  参考文献：
  名称：

  [EN] BICYCLIC HETEROAROMATIC DERIVATIVES AS MODULATORS OF CXCR3 FUNCTION
  [FR] DERIVES HETEROAROMATIQUES BICYCLIQUES EN TANT QUE MODULATEURS DE LA FONCTION CXCR3

  摘要：

  一类1-取代的4-(苯并噻唑-2-基氨基)哌啶衍生物及相关的杂环化合物，是CXCR3与其趋化因子配体相互作用的有效和选择性调节剂，因此可用于治疗和/或预防涉及不适当T细胞迁移的疾病，包括炎症性、自身免疫和免疫调节性疾病。

  公开号：

  WO2005003127A1
• 作为产物：
  描述：

  2-氯苯并恶唑 、 1-(((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)piperidin-4-amine 在 三乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 N-(benzoxazol-2-yl)-N-[1-((1R,5S)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl)-piperidin-4-yl]amine
  参考文献：
  名称：

  Development of CXCR3 antagonists. Part 2: Identification of 2-amino(4-piperidinyl)azoles as potent CXCR3 antagonists

  摘要：

  Development of a lead series of piperidinylurea CXCR3 antagonists has led to the identification of molecules with alternative linkages which retain good potency. A novel 5-(piperidin-4-yl)amino-1,2,4-thiadiazole derivative was found to have satisfactory in vitro metabolic stability and to be orally bioavailable in mice, giving high plasma concentrations and a half life of 5.4 h. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.029

文献信息

• [EN] BICYCLIC HETEROAROMATIC DERIVATIVES AS MODULATORS OF CXCR3 FUNCTION<br/>[FR] DERIVES HETEROAROMATIQUES BICYCLIQUES EN TANT QUE MODULATEURS DE LA FONCTION CXCR3
  申请人：CELLTECH R&D LTD

  公开号：WO2005003127A1

  公开（公告）日：2005-01-13

  A class of 1-substituted 4-(benzothiazol-2-ylamino) piperidine derivatives and related heterocyclic compounds, being potent and selective modulators of the interaction between CXCR3 and its chemokine ligands, are accordingly of use in the treatment and/or prevention of conditions involving inappropriate T-cell trafficking, including inflammatory, autoimmune and immunoregulatory disorders.

  一类1-取代的4-(苯并噻唑-2-基氨基)哌啶衍生物及相关的杂环化合物，是CXCR3与其趋化因子配体相互作用的有效和选择性调节剂，因此可用于治疗和/或预防涉及不适当T细胞迁移的疾病，包括炎症性、自身免疫和免疫调节性疾病。
• Development of CXCR3 antagonists. Part 2: Identification of 2-amino(4-piperidinyl)azoles as potent CXCR3 antagonists
  作者：Robert J. Watson、Daniel R. Allen、Helen L. Birch、Gayle A. Chapman、Duncan R. Hannah、Roland L. Knight、Johannes W.G. Meissner、David A. Owen、Elizabeth J. Thomas

  DOI：10.1016/j.bmcl.2007.10.029

  日期：2007.12

  Development of a lead series of piperidinylurea CXCR3 antagonists has led to the identification of molecules with alternative linkages which retain good potency. A novel 5-(piperidin-4-yl)amino-1,2,4-thiadiazole derivative was found to have satisfactory in vitro metabolic stability and to be orally bioavailable in mice, giving high plasma concentrations and a half life of 5.4 h. (c) 2007 Elsevier Ltd. All rights reserved.