5-chloro-6-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-(hydroxymethyl)piperazin-1-yl)-N-methylnicotinamide | 1279723-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5-chloro-6-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-(hydroxymethyl)piperazin-1-yl)-N-methylnicotinamide
• 英文别名: 5-chloro-6-[4-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-3-(hydroxymethyl)piperazin-1-yl]-N-methylpyridine-3-carboxamide
• CAS: 1279723-79-3
• 化学式: C₂₄H₃₁Cl₂N₅O₂
• 分子量: 492.448
• InChiKey: PONAOOISGRZJDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-chloro-6-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-(hydroxymethyl)piperazin-1-yl)-N-methylnicotinamide 、 三甲基硅烷化重氮甲烷 在 tetrafluoroboric acid 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以72%的产率得到5-chloro-6-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-(methoxymethyl)piperazin-1-yl)-N-methylnicotinamide
  参考文献：
  名称：

  II. SAR studies of pyridyl–piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists

  摘要：

  The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC(50) of 0.2 nM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.114
• 作为产物：
  描述：

  Methyl 4-(3-chloro-5-(methylcarbamoyl)pyridin-2-yl)-1-(1-(4-chlorobenzyl)piperidin-4-yl)piperazine-2-carboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到5-chloro-6-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-(hydroxymethyl)piperazin-1-yl)-N-methylnicotinamide
  参考文献：
  名称：

  II. SAR studies of pyridyl–piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists

  摘要：

  The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC(50) of 0.2 nM. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.114

文献信息

• II. SAR studies of pyridyl–piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists
  作者：Yuefei Shao、Gopinadhan N. Anilkumar、Carolyn DiIanni Carroll、Guizhen Dong、James W. Hall、Doug W. Hobbs、Yueheng Jiang、Chung-Her Jenh、Seong Heon Kim、Joseph A. Kozlowski、Brian F. McGuinness、Stuart B. Rosenblum、Inna Schulman、Neng-Yang Shih、Youheng Shu、Michael K.C. Wong、Wensheng Yu、Lisa Guise Zawacki、Qingbei Zeng

  DOI：10.1016/j.bmcl.2010.12.114

  日期：2011.3

  The structure-human CXCR3 binding affinity relationship of a series of pyridyl-piperazinyl-piperidine derivatives was explored. The optimization campaign highlighted the pronounced effect of 2'-piperazine substitution on CXCR3 receptor affinity. Analog 18j, harboring a 2'(S)-ethylpiperazine moiety, exhibited a human CXCR3 IC(50) of 0.2 nM. (C) 2011 Elsevier Ltd. All rights reserved.