3-(adamantan-1-yl)-5-(4-methyl-1H-imidazol-1-yl)aniline | 1290090-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(adamantan-1-yl)-5-(4-methyl-1H-imidazol-1-yl)aniline
• CAS: 1290090-23-1
• 化学式: C₂₀H₂₅N₃
• 分子量: 307.439
• InChiKey: QNOVQYLGTFEAOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  43.84
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(adamantan-1-yl)-5-(4-methyl-1H-imidazol-1-yl)aniline 、 (R)-2-(methyl(pyrimidin-5-yl)amino)-2,3-dihydro-1H-indene-5-carboxylic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以25%的产率得到(R)-N-(3-(adamantan-1-yl)-5-(4-methyl-1H-imidazol-1-yl)phenyl)-2-(methyl(pyrimidin-5-yl)amino)-2,3-dihydro-1H-indene-5-carboxamide
  参考文献：
  名称：

  2-Amino-2,3-dihydro-1H-indene-5-carboxamide-Based Discoidin Domain Receptor 1 (DDR1) Inhibitors: Design, Synthesis, and in Vivo Antipancreatic Cancer Efficacy

  摘要：

  A series of 2-amino-2,3-dihydro-1H-indene-5-carboxamides were designed and synthesized as new selective discoidin domain receptor 1 (DDR1) inhibitors. One of the representative compounds, 7f, bound with DDR1 with a K-d value of 5.9 nM and suppressed the kinase activity with an half-maximal (50%) inhibitory concentration value of 14.9 nM. 7f potently inhibited collagen-induced DDR1 signaling and epithelial-mesenchymal transition, dose-dependently suppressed colony formation of pancreatic cancer cells, and exhibited promising in vivo therapeutic efficacy in orthotopic mouse models of pancreatic cancer.

  DOI：

  10.1021/acs.jmedchem.9b00365
• 作为产物：
  描述：

  4-甲基咪唑 、 在 copper(l) iodide 、 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-(adamantan-1-yl)-5-(4-methyl-1H-imidazol-1-yl)aniline
  参考文献：
  名称：

  Hybrid compounds as new Bcr/Abl inhibitors

  摘要：

  A series of 2,4-disubstituted thiazole derivatives were designed and synthesized as new Bcr/Abl inhibitors by hybriding the structural moieties from FDA approved imatinib, nilotinib and dasatinib. The new inhibitors strongly suppressed the activity of Bcr/Abl kinase and potently inhibited the proliferation of K562 and KU812 leukemia cancer cells. Compound 4i displayed comparable potency with that of nilotinib in both biochemical kinase assay and cancer cell growth inhibition assay. These inhibitors might serve as lead compounds for further developing new anticancer drugs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.029