1-[(3-methoxy-4-nitrophenyl)methyl]-1H-imidazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(3-methoxy-4-nitrophenyl)methyl]-1H-imidazole
• 英文别名: 1-[(3-methoxy-4-nitrophenyl)methyl]imidazole
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: PMTDIUBNLUWYEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(3-methoxy-4-nitrophenyl)methyl]-1H-imidazole 在 铁粉 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of azole-diphenylpyrimidine derivatives (AzDPPYs) as potent T790M mutant form of epidermal growth factor receptor inhibitors

  摘要：

  A series of novel azole-diphenylpyrimidine derivatives (AzDPPYs) were synthesized and biologically evaluated as potent EGFR(T790M) inhibitors. Among these analogues, the most active inhibitor 6e not only displayed high activity against EGFR(T790M/L858R) kinase (IC50 = 33 nM), but also was able to repress the replication of H1975 cells harboring EGFR(T790M) mutation at a concentration of 0.118 mu mol/L. In contrast to the lead compound rociletinib, 6e slightly reduces the key EGFRT790M-minduced drug resistance. Significantly, inhibitor 6e demonstrates high selectivity (SI = 299.3) for T790M-containing EGFR mutants over wild type EGFR, hinting that it will cause less side effects. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.09.001
• 作为产物：
  描述：

  1-[(3-methoxyphenyl)methyl]-1H-imidazole mononitrate 在 ammonium hydroxide 、 硫酸 、 硝酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以28.2 parts (40.3%)的产率得到1-[(3-methoxy-4-nitrophenyl)methyl]-1H-imidazole
  参考文献：
  名称：

  (1H-azol-1-ylmethyl) substituted benzotriazole derivatives and

  摘要：

  (1H-咪唑-1-基)取代苯并三唑衍生物，含有这些衍生物的组合物，以及治疗雌激素依赖性疾病的方法。

  公开号：

  US04943574A1

文献信息

• 6-(1H-azol-1-ylmethyl)-1-(pyrimidinyloxy)-1H benzotriazoles
  申请人：Janssen Pharmaceutica N.V.

  公开号：US05039677A1

  公开（公告）日：1991-08-13

  (1H-azol-1-ylmethyl)substituted benzotriazole derivatives, compositions containing the same, and methods of treating estrogen dependent disorders.

  含有(1H-唑-1-基)取代苯并三唑衍生物的组合物，以及治疗雌激素依赖性疾病的方法。
• (1H-azol-1-ylmethyl)substituted benzotriazole derivatives
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP0293978A2

  公开（公告）日：1988-12-07

  Novel (1H-azol-1-ylmethyl)substituted benzotriazole derivatives of formula wherein     A¹=A²-A³=A⁴ is -CH=N-CH=CH-, -CH=N-CH=N- or -CH=N-N=CH-;     R is hydrogen or C₁₋₆alkyl;     R¹ is hydrogen, C₁₋₁₀ alkyl, C₃₋₇cycloalkyl, Ar¹, Ar²-C₁₋₆alkyl, C₂₋₆alkenyl or C₂₋₆alkynyl;     R² is hydrogen; optionally substituted C₁₋₁₀alkyl; Ar¹; C₂₋₆alkenyl; C₂₋₆alkynyl; C₃₋₇cycloalkyl; bicyclo[2.2.1]heptan-­2-yl; 2,3-dihydro-1H-indenyl; 1,2,3,4-tetrahydronaphthalenyl; hydroxy; optionally substituted C₂₋₆alkenyloxy; C₂₋₆alkynyloxy; pyrimidinyl­oxy; di(Ar²)methoxy; (1-C₁₋₄alkyl-4-piperidinyl)oxy; or optionally substituted C₁₋₁₀alkyloxy;     R³ is hydrogen, nitro, amino, mono- and di(C₁₋₆alkyl)amino, halo, C₁₋₆alkyl, hydroxy or C₁₋₆alkyloxy;     wherein Ar¹ is phenyl, substituted phenyl, naphthalenyl, pyridinyl, aminopyridinyl, imidazolyl, triazolyl, thienyl, halothienyl, furanyl, C₁₋₆alkylfuranyl, halofuranyl or thiazolyl; and     Ar² is phenyl, substituted phenyl or pyridinyl; the pharmaceutically acceptable acid addition salts and possible stereochemically isomeric forms thereof, which compounds are estrogene hormone biosynthesis inhibitory agents; pharmaceutical compositions containing such compounds as an active ingredient and methods of preparing said compounds and pharmaceutical compositions.

  式中的新颖(1H-唑-1-基甲基)取代苯并三唑衍生物 其中 A¹=A²-A³=A⁴ 是 -CH=N-CH=CH-、-CH=N-CH=N- 或 -CH=N-N=CH-； R 是氢或 C₁₋₆ 烷基； R¹ 是氢、C₁₋₁₀烷基、C₃₋₇环烷基、Ar¹、Ar²-C₁₋₆烷基、C₂₋₆ 炔基； R² 是氢；任选取代的 C₁₋₁₀烷基；Ar¹；C₂₋₆烯基；C₂₋₆炔基；C₃₋₇环烷基；双环[2.2.1]庚-2-基；2,3-二氢-1H-茚基；1,2,3,4-四氢萘基；羟基；任选取代的 C₂₋₆烯氧基；C₂₋₆炔氧基；嘧啶氧基；二(Ar²)甲氧基；(1-C₁₋₄烷基-4-哌啶基)氧基；或任选取代的 C₁₋₁₀烷氧基； R³ 是氢、硝基、氨基、单-和二(C₁₋₆烷基)氨基、卤代、C₁₋₆烷基、羟基或 C₁₋₆烷氧基； 其中 Ar¹ 是苯基、取代苯基、萘基、吡啶基、氨基吡啶基、咪唑基、三唑基、噻吩基、卤代噻吩基、呋喃基、C₁₋₆烷基呋喃基、卤代呋喃基或噻唑基；以及 Ar² 是苯基、取代苯基或吡啶基； 药学上可接受的酸加成盐及其可能的立体化学异构体形式，这些化合物是雌 激素激素生物合成抑制剂；含有这些化合物作为活性成分的药物组合物，以及制备 上述化合物和药物组合物的方法。
• US4943574A
  申请人：——

  公开号：US4943574A

  公开（公告）日：1990-07-24
• US5039677A
  申请人：——

  公开号：US5039677A

  公开（公告）日：1991-08-13
• Synthesis and biological evaluation of azole-diphenylpyrimidine derivatives (AzDPPYs) as potent T790M mutant form of epidermal growth factor receptor inhibitors
  作者：Zhendong Song、Yue Jin、Yang Ge、Changyuan Wang、Jianbin Zhang、Zeyao Tang、Jinyong Peng、Kexin Liu、Yanxia Li、Xiaodong Ma

  DOI：10.1016/j.bmc.2016.09.001

  日期：2016.11

  A series of novel azole-diphenylpyrimidine derivatives (AzDPPYs) were synthesized and biologically evaluated as potent EGFR(T790M) inhibitors. Among these analogues, the most active inhibitor 6e not only displayed high activity against EGFR(T790M/L858R) kinase (IC50 = 33 nM), but also was able to repress the replication of H1975 cells harboring EGFR(T790M) mutation at a concentration of 0.118 mu mol/L. In contrast to the lead compound rociletinib, 6e slightly reduces the key EGFRT790M-minduced drug resistance. Significantly, inhibitor 6e demonstrates high selectivity (SI = 299.3) for T790M-containing EGFR mutants over wild type EGFR, hinting that it will cause less side effects. (C) 2016 Elsevier Ltd. All rights reserved.