methyl 3-amino-5-[(3S)-4-[1-(2-amino-6-chloropyridine-3-carbonyl)piperidin-4-yl]-3-ethylpiperazin-1-yl]-6-chloropyrazine-2-carboxylate | 908345-24-4

• 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: methyl 3-amino-5-[(3S)-4-[1-(2-amino-6-chloropyridine-3-carbonyl)piperidin-4-yl]-3-ethylpiperazin-1-yl]-6-chloropyrazine-2-carboxylate
• CAS: 908345-24-4
• 化学式: C₂₃H₃₀Cl₂N₈O₃
• 分子量: 537.449
• InChiKey: WHDKJHNHYAHREU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-5-[(3S)-4-[1-(2-amino-6-chloropyridine-3-carbonyl)piperidin-4-yl]-3-ethylpiperazin-1-yl]-6-chloropyrazine-2-carboxylate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 16.0h， 生成 lithium;3-amino-5-[(3S)-4-[1-(2-amino-6-chloropyridine-3-carbonyl)piperidin-4-yl]-3-ethylpiperazin-1-yl]-6-chloropyrazine-2-carboxylate
  参考文献：
  名称：

  WO2006/91428

  摘要：

  公开号：
• 作为产物：
  描述：

  methyl 3-amino-6-chloro-5-[(3S)-3-ethyl-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]piperazin-1-yl]pyrazine-2-carboxylate 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 methyl 3-amino-5-[(3S)-4-[1-(2-amino-6-chloropyridine-3-carbonyl)piperidin-4-yl]-3-ethylpiperazin-1-yl]-6-chloropyrazine-2-carboxylate
  参考文献：
  名称：

  III. Identification of novel CXCR3 chemokine receptor antagonists with a pyrazinyl–piperazinyl–piperidine scaffold

  摘要：

  The SAR of a novel pyrazinyl-piperazinyl-piperidine scaffold with CXCR3 receptor antagonist activity was explored. Optimization of the DMPK profile and reduction of hERG inhibition is described. Compound 16e with single-digit CXCR3 affinity, good rat PK and hERG profiles has been identified as a lead for further study. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.120

文献信息

• HETEROARYL SUBSTITUTED PYRAZINYL-PIPERAZINE-PIPERIDINES WITH CXCR3 ANTAGONIST ACTIVITY
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1858888B1

  公开（公告）日：2013-04-17
• US7879838B2
  申请人：——

  公开号：US7879838B2

  公开（公告）日：2011-02-01
• WO2006/91428
  申请人：——

  公开号：——

  公开（公告）日：——
• III. Identification of novel CXCR3 chemokine receptor antagonists with a pyrazinyl–piperazinyl–piperidine scaffold
  作者：Seong Heon Kim、Gopinadhan N. Anilkumar、Lisa Guise Zawacki、Qingbei Zeng、De-Yi Yang、Yuefei Shao、Guizhen Dong、Xiaolian Xu、Wensheng Yu、Yueheng Jiang、Chung-Her Jenh、James W. Hall、Carolyn DiIanni Carroll、Doug W. Hobbs、John J. Baldwin、Brian F. McGuinness、Stuart B. Rosenblum、Joseph A. Kozlowski、Bandarpalle B. Shankar、Neng-Yang Shih

  DOI：10.1016/j.bmcl.2011.09.120

  日期：2011.12

  The SAR of a novel pyrazinyl-piperazinyl-piperidine scaffold with CXCR3 receptor antagonist activity was explored. Optimization of the DMPK profile and reduction of hERG inhibition is described. Compound 16e with single-digit CXCR3 affinity, good rat PK and hERG profiles has been identified as a lead for further study. (C) 2011 Elsevier Ltd. All rights reserved.