(1R,2S,3R,5R)-3-[[2-amino-6-chloro-5-[(Z)-2-pyridin-3-ylethenyl]pyrimidin-4-yl]amino]-5-(hydroxymethyl)cyclopentane-1,2-diol | 1357457-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (1R,2S,3R,5R)-3-[[2-amino-6-chloro-5-[(Z)-2-pyridin-3-ylethenyl]pyrimidin-4-yl]amino]-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS: 1357457-29-4
• 化学式: C₁₇H₂₀ClN₅O₃
• 分子量: 377.831
• InChiKey: UXTNRWBXUJMHJT-LTPKJMNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1R,2S,3R,4R)-2,3-二羟基-4-(羟甲基)-1-氨基环戊烷水电氯化物 、 (Z)-4,6-dichloro-5-(2-(pyridin-3-yl)vinyl)pyrimidin-2-amine 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 (1R,2S,3R,5R)-3-[[2-amino-6-chloro-5-[(Z)-2-pyridin-3-ylethenyl]pyrimidin-4-yl]amino]-5-(hydroxymethyl)cyclopentane-1,2-diol
  参考文献：
  名称：

  Novel substituted pyrimidines as HCV replication (replicase) inhibitors

  摘要：

  Compound I was identified as a HCV replication inhibitor from screening/early SAR triage. Potency improvement was achieved via modulation of substituent on the 5-azo linkage. Due to potential toxicological concern, the 5-azo linkage was replaced with 5-alkenyl or 5-alkynyl moiety. Analogs containing the 5-alkynyl linkage were found to be potent inhibitors of HCV replication. Further evaluation identified compounds 53 and 63 with good overall profile, in terms of replicon potency, selectivity and in vivo characteristics. Initial target engagement studies suggest that these novel carbanucleoside-like derivatives may inhibit the HCV replication complex (replicase). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.091

文献信息

• Novel substituted pyrimidines as HCV replication (replicase) inhibitors
  作者：Cecil D. Kwong、Jeremy L. Clark、Anita T. Fowler、Feng Geng、Hollis S. Kezar、Abhijit Roychowdhury、Robert C. Reynolds、Joseph A. Maddry、Subramaniam Ananthan、John A. Secrist、Neng-Yang Shih、John J. Piwinski、Cheng Li、Boris Feld、Hsueh-Cheng Huang、Xiao Tong、F. George Njoroge、Ashok Arasappan

  DOI：10.1016/j.bmcl.2011.11.091

  日期：2012.1

  Compound I was identified as a HCV replication inhibitor from screening/early SAR triage. Potency improvement was achieved via modulation of substituent on the 5-azo linkage. Due to potential toxicological concern, the 5-azo linkage was replaced with 5-alkenyl or 5-alkynyl moiety. Analogs containing the 5-alkynyl linkage were found to be potent inhibitors of HCV replication. Further evaluation identified compounds 53 and 63 with good overall profile, in terms of replicon potency, selectivity and in vivo characteristics. Initial target engagement studies suggest that these novel carbanucleoside-like derivatives may inhibit the HCV replication complex (replicase). (C) 2011 Elsevier Ltd. All rights reserved.