2-((4-chloro-6-(pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino)-N-ethyl-2,3-dihydro-1H-indene-2-carboxamide | 1590462-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-((4-chloro-6-(pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino)-N-ethyl-2,3-dihydro-1H-indene-2-carboxamide
• CAS: 1590462-73-9
• 化学式: C₁₉H₂₃ClN₆O
• 分子量: 386.884
• InChiKey: VYVRYDGCOSAMJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  83.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,4-二氯苯乙胺 、 2-((4-chloro-6-(pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino)-N-ethyl-2,3-dihydro-1H-indene-2-carboxamide 在 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 以28%的产率得到2-((4-((3,4-dichlorophenethyl)amino)-6-(pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino)-N-ethyl-2,3-dihydro-1H-indene-2-carboxamide
  参考文献：
  名称：

  Application of encoded library technology (ELT) to a protein–protein interaction target: Discovery of a potent class of integrin lymphocyte function-associated antigen 1 (LFA-1) antagonists

  摘要：

  The inhibition of protein-protein interactions remains a challenge for traditional small molecule drug discovery. Here we describe the use of DNA-encoded library technology for the discovery of small molecules that are potent inhibitors of the interaction between lymphocyte function-associated antigen 1 and its ligand intercellular adhesion molecule 1. A DNA-encoded library with a potential complexity of 4.1 billion compounds was exposed to the I-domain of the target protein and the bound ligands were affinity selected, yielding an enriched small-molecule hit family. Compounds representing this family were synthesized without their DNA encoding moiety and found to inhibit the lymphocyte function-associated antigen 1/intercellular adhesion molecule-1 interaction with submicromolar potency in both ELISA and cell adhesion assays. Re-synthesized compounds conjugated to DNA or a fluorophore were demonstrated to bind to cells expressing the target protein. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.050
• 作为产物：
  描述：

  N-叔丁氧羰基-2-氨基茚满-2-羧酸 在 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.25h， 生成 2-((4-chloro-6-(pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino)-N-ethyl-2,3-dihydro-1H-indene-2-carboxamide
  参考文献：
  名称：

  Application of encoded library technology (ELT) to a protein–protein interaction target: Discovery of a potent class of integrin lymphocyte function-associated antigen 1 (LFA-1) antagonists

  摘要：

  The inhibition of protein-protein interactions remains a challenge for traditional small molecule drug discovery. Here we describe the use of DNA-encoded library technology for the discovery of small molecules that are potent inhibitors of the interaction between lymphocyte function-associated antigen 1 and its ligand intercellular adhesion molecule 1. A DNA-encoded library with a potential complexity of 4.1 billion compounds was exposed to the I-domain of the target protein and the bound ligands were affinity selected, yielding an enriched small-molecule hit family. Compounds representing this family were synthesized without their DNA encoding moiety and found to inhibit the lymphocyte function-associated antigen 1/intercellular adhesion molecule-1 interaction with submicromolar potency in both ELISA and cell adhesion assays. Re-synthesized compounds conjugated to DNA or a fluorophore were demonstrated to bind to cells expressing the target protein. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.050