3-methyl-5-(4-methylimidazol-1-yl)aniline | 1290090-19-5

• 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-methyl-5-(4-methylimidazol-1-yl)aniline
• CAS: 1290090-19-5
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: VOVJROXRJUTSAA-UHFFFAOYSA-N

物化性质

• 沸点：
  399.9±37.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoyl chloride 、 3-methyl-5-(4-methylimidazol-1-yl)aniline 在 水 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 nilotinib
  参考文献：
  名称：

  Synthesis and biological evaluation of analogues of the kinase inhibitor nilotinib as Abl and Kit inhibitors

  摘要：

  The importance of the trifluoromethyl group in the polypharmacological profile of nilotinib was investigated. Molecular editing of nilotinib led to the design, synthesis and biological evaluation of analogues where the trifluoromethyl group was replaced by a proton, fluorine and a methyl group. While these analogues were less active than nilotinib toward Abl, their activity toward Kit was comparable, with the monofluorinated analogue being the most active. Docking of nilotinib and of analogues 2a-c to the binding pocket of Abl and of Kit showed that the lack of shape complementarity in Kit is compensated by the stabilizing effect from its juxtamembrane region. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.11.111
• 作为产物：
  描述：

  3-碘-5-硝基甲苯 在 copper(I) oxide 、 tin(II) chloride dihdyrate 、 4,7-二甲氧基-1,10-菲咯啉 、 caesium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 3-methyl-5-(4-methylimidazol-1-yl)aniline
  参考文献：
  名称：

  Synthesis and biological evaluation of analogues of the kinase inhibitor nilotinib as Abl and Kit inhibitors

  摘要：

  The importance of the trifluoromethyl group in the polypharmacological profile of nilotinib was investigated. Molecular editing of nilotinib led to the design, synthesis and biological evaluation of analogues where the trifluoromethyl group was replaced by a proton, fluorine and a methyl group. While these analogues were less active than nilotinib toward Abl, their activity toward Kit was comparable, with the monofluorinated analogue being the most active. Docking of nilotinib and of analogues 2a-c to the binding pocket of Abl and of Kit showed that the lack of shape complementarity in Kit is compensated by the stabilizing effect from its juxtamembrane region. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.11.111

文献信息

• PROCESS FOR THE PREPARATION OF NILOTINIB
  申请人：Kompella Amala

  公开号：US20130210847A1

  公开（公告）日：2013-08-15

  The present invention relates a process for the preparation of a compound of formula (I): or a pharmaceutically acceptable salt thereof, which process comprises converting a compound of formula (IV): or a pharmaceutically acceptable salt thereof, into the compound of formula (I) or a pharmaceutically acceptable salt thereof.

  本发明涉及一种用于制备化合物的方法的公式(I)：或其药用可接受盐，该方法包括将公式(IV)的化合物：或其药用可接受盐转化为公式(I)的化合物或其药用可接受盐。
• HETEROCYCLIC ALKYNYL BENZENE COMPOUNDS AND MEDICAL COMPOSITIONS AND USES THEREOF
  申请人：Ding Ke

  公开号：US20130196985A1

  公开（公告）日：2013-08-01

  The heterocyclic alkynyl benzene compounds of formula (I), their pharmaceutically acceptable salts and stereoisomers thereof, as well as application in preparing drugs for preventing or treating tumors. The compounds can overcome the clinically induced resistance against Gleevec.

  式（I）的杂环炔基苯化合物，其药用盐及其立体异构体，以及在制备用于预防或治疗肿瘤的药物中的应用。这些化合物可以克服临床诱导的对格列卫（Gleevec）的耐药性。
• NILOTINIB INTERMEDIATES AND PREPARATION THEREOF
  申请人：WANG Yanling

  公开号：US20100016590A1

  公开（公告）日：2010-01-21

  Intermediates of Nilotinib were prepared, including, for example, 3-(trifluoromethyl-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine; 3-(4-(pyridin-3-yl)pyrimidin-2-ylamino) -4-methylbenzoyl halogen dihydrochloride; and N-(3-Bromo-5-trifluoromethylphenyl)-4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzamide. Nilotinib.3HCl and its crystalline forms are also described.

  尼洛替尼的中间体已经制备好，包括例如3-(三氟甲基-5-(4-甲基-1H-咪唑-1-基)-苯胺；3-(4-(吡啶-3-基)嘧啶-2-基氨基)-4-甲基苯甲酰卤代二盐酸盐；以及N-(3-溴-5-三氟甲基苯基)-4-甲基-3-[[4-(3-吡啶基)-2-嘧啶基]氨基]苯甲酰胺。另外还描述了尼洛替尼.3HCl及其结晶形式。
• PROCESS FOR THE SYNTHESIS OF ORGANIC COMPOUNDS
  申请人：Abel Stephan

  公开号：US20100280257A1

  公开（公告）日：2010-11-04

  The present invention provides an efficient, safe and cost effective way to prepare 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine which is a key intermediate for the preparation of substituted pyrimidinylaminobenzamides of formula (II):

  本发明提供了一种高效、安全且成本效益高的方法，用于制备5-(4-甲基-1H-咪唑-1-基)-3-(三氟甲基)-苯胺，该化合物是制备式（II）取代嘧啶基氨基苯甲酰胺的重要中间体。
• 2-Amino-2,3-dihydro-1<i>H</i>-indene-5-carboxamide-Based Discoidin Domain Receptor 1 (DDR1) Inhibitors: Design, Synthesis, and in Vivo Antipancreatic Cancer Efficacy
  作者：Dongsheng Zhu、Huocong Huang、Daniel M. Pinkas、Jinfeng Luo、Debolina Ganguly、Alice E. Fox、Emily Arner、Qiuping Xiang、Zheng-Chao Tu、Alex N. Bullock、Rolf A. Brekken、Ke Ding、Xiaoyun Lu

  DOI：10.1021/acs.jmedchem.9b00365

  日期：2019.8.22

  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.