4-((1-methyl-1H-imidazol-2-yl)methylamino)phenol | 1250848-33-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-((1-methyl-1H-imidazol-2-yl)methylamino)phenol
• 英文别名: 4-[(1-Methylimidazol-2-yl)methylamino]phenol
• CAS: 1250848-33-9
• 化学式: C₁₁H₁₃N₃O
• 分子量: 203.244
• InChiKey: LUULUFCZHKKTNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 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：
  50.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 4-((1-methyl-1H-imidazol-2-yl)methylamino)phenol 在 盐酸 作用下， 以 水 为溶剂， 以76%的产率得到4-((1-methyl-1H-imidazol-2-yl)methylamino)phenoldichloroplatinum(II)
  参考文献：
  名称：

  Cytotoxic effect of (1-methyl-1 H -imidazol-2-yl)-methanamine and its derivatives in Pt II complexes on human carcinoma cell lines: A comparative study with cisplatin

  摘要：

  The synthesis and pharmacological characterisation of (1-methyl-1H-imidazol-2-yl)-methanamine and its derivatives in Pt-II complexes are described. Six out of eleven new Pt-II complexes showed a significant cytotoxic effect on NCI-H460 lung cancer cell line with EC50 values between 1.1 and 0.115 mM, determined by MTT assay. Compound Pt-4a showed a particularly more potent cytotoxic effect than the previously described Pt-II complex with 2,2'-bipyridine, [Pt(bpy)Cl-2], with an EC50 value equal to 172.7 mu M versus 726.5 mu M respectively, and similar potency of cisplatin (EC50 = 78.3 mu M) in NCI-H460 cell line. The determination of the intracellular and DNA-bound concentrations of Pt-195, as marker of the presence of the complexes, showed that the cytotoxic compound Pt-4a readily diffused into the cells to a similar extent of cisplatin and directly interacted with the nuclear DNA. Pt-4a induced both p53 and p21(Waf) expression in NCI-H460 cells similar to cisplatin. A direct comparison of the cytotoxic effect between compound Pt-4a and cisplatin on 12 different cancer cell lines demonstrated that compound Pt-4a was in general less potent than cisplatin, but it had a comparable cytotoxic effect on non-small-cell lung cancer NCI-H460 cells, and the colorectal cancer cells HCT-15 and HCT-116. Altogether, these results suggested that the Pt-II complex with 1-methyl-1H-imidazol-2-yl)-methanamine (compound Pt-4a), displayed a significant cytotoxic activity in cancer cells. Similarly to cisplatin this compound interacts with nuclear DNA and induces both p53 and p21(waf), and thus it represents an interesting starting point for future optimisation of new Pt-II complexes forming DNA adducts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.063
• 作为产物：
  描述：

  4-((1-methyl-1H-imidazol-2-yl)methyleneamino)phenol 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、2.03 MPa 条件下， 反应 24.0h， 以95%的产率得到4-((1-methyl-1H-imidazol-2-yl)methylamino)phenol
  参考文献：
  名称：

  Cytotoxic effect of (1-methyl-1 H -imidazol-2-yl)-methanamine and its derivatives in Pt II complexes on human carcinoma cell lines: A comparative study with cisplatin

  摘要：

  The synthesis and pharmacological characterisation of (1-methyl-1H-imidazol-2-yl)-methanamine and its derivatives in Pt-II complexes are described. Six out of eleven new Pt-II complexes showed a significant cytotoxic effect on NCI-H460 lung cancer cell line with EC50 values between 1.1 and 0.115 mM, determined by MTT assay. Compound Pt-4a showed a particularly more potent cytotoxic effect than the previously described Pt-II complex with 2,2'-bipyridine, [Pt(bpy)Cl-2], with an EC50 value equal to 172.7 mu M versus 726.5 mu M respectively, and similar potency of cisplatin (EC50 = 78.3 mu M) in NCI-H460 cell line. The determination of the intracellular and DNA-bound concentrations of Pt-195, as marker of the presence of the complexes, showed that the cytotoxic compound Pt-4a readily diffused into the cells to a similar extent of cisplatin and directly interacted with the nuclear DNA. Pt-4a induced both p53 and p21(Waf) expression in NCI-H460 cells similar to cisplatin. A direct comparison of the cytotoxic effect between compound Pt-4a and cisplatin on 12 different cancer cell lines demonstrated that compound Pt-4a was in general less potent than cisplatin, but it had a comparable cytotoxic effect on non-small-cell lung cancer NCI-H460 cells, and the colorectal cancer cells HCT-15 and HCT-116. Altogether, these results suggested that the Pt-II complex with 1-methyl-1H-imidazol-2-yl)-methanamine (compound Pt-4a), displayed a significant cytotoxic activity in cancer cells. Similarly to cisplatin this compound interacts with nuclear DNA and induces both p53 and p21(waf), and thus it represents an interesting starting point for future optimisation of new Pt-II complexes forming DNA adducts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.063

文献信息

• Cytotoxic effect of (1-methyl-1 H -imidazol-2-yl)-methanamine and its derivatives in Pt II complexes on human carcinoma cell lines: A comparative study with cisplatin
  作者：Nicola Ferri、Stefano Cazzaniga、Luca Mazzarella、Giuseppe Curigliano、Giorgio Lucchini、Daniele Zerla、Raffaella Gandolfi、Giorgio Facchetti、Michela Pellizzoni、Isabella Rimoldi

  DOI：10.1016/j.bmc.2013.01.063

  日期：2013.4

  The synthesis and pharmacological characterisation of (1-methyl-1H-imidazol-2-yl)-methanamine and its derivatives in Pt-II complexes are described. Six out of eleven new Pt-II complexes showed a significant cytotoxic effect on NCI-H460 lung cancer cell line with EC50 values between 1.1 and 0.115 mM, determined by MTT assay. Compound Pt-4a showed a particularly more potent cytotoxic effect than the previously described Pt-II complex with 2,2'-bipyridine, [Pt(bpy)Cl-2], with an EC50 value equal to 172.7 mu M versus 726.5 mu M respectively, and similar potency of cisplatin (EC50 = 78.3 mu M) in NCI-H460 cell line. The determination of the intracellular and DNA-bound concentrations of Pt-195, as marker of the presence of the complexes, showed that the cytotoxic compound Pt-4a readily diffused into the cells to a similar extent of cisplatin and directly interacted with the nuclear DNA. Pt-4a induced both p53 and p21(Waf) expression in NCI-H460 cells similar to cisplatin. A direct comparison of the cytotoxic effect between compound Pt-4a and cisplatin on 12 different cancer cell lines demonstrated that compound Pt-4a was in general less potent than cisplatin, but it had a comparable cytotoxic effect on non-small-cell lung cancer NCI-H460 cells, and the colorectal cancer cells HCT-15 and HCT-116. Altogether, these results suggested that the Pt-II complex with 1-methyl-1H-imidazol-2-yl)-methanamine (compound Pt-4a), displayed a significant cytotoxic activity in cancer cells. Similarly to cisplatin this compound interacts with nuclear DNA and induces both p53 and p21(waf), and thus it represents an interesting starting point for future optimisation of new Pt-II complexes forming DNA adducts. (C) 2013 Elsevier Ltd. All rights reserved.