1-(2-Methoxyethyl)-3,5-diphenylpyrazole | 1616859-07-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-Methoxyethyl)-3,5-diphenylpyrazole
• 英文别名: 1-(2-methoxyethyl)-3,5-diphenylpyrazole
• CAS: 1616859-07-4
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: BHVILQLFZWWBNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium tetrachloropalladate 、 1-(2-Methoxyethyl)-3,5-diphenylpyrazole 以 甲醇 为溶剂， 反应 2.0h， 以78%的产率得到trans-[Pd[1-{MeO-(CH2)2-}-3,5-Ph2-(C3HN2)]2Cl2]
  参考文献：
  名称：

  Pd(II) complexes with N-substituted pyrazoles as ligands. The influence of the R group [OMe versus NMe2] of [1-{R–(CH2)2–}-3,5-Ph2–(C3HN2)] on their cytotoxic activity on breast cancer cell lines

  摘要：

  The study of the reactivity of the novel pyrazole derivative [1-{MeOe(CH2)(2)-}-3,5-PH2-(C3HN2)] (1) with Na-2[PdCl4] or Pd(OAc)(2) under different experimental conditions has allowed us to isolate and characterize the trans-isomers of [Pd{[1-{MeOe(CH2)(2)-}-3,5-PH2-(C3HN2)]}(2)(X)(2)] [X = Cl (2) or OAc (3)] and the di-m-ligand bridged cyclopalladated complexes [Pd{kappa(2),C,N[1-{MeOe(CH2)(2)-}-3-(C6H4), 5-Ph-(C3HN2)]}(mu-X)](2) [X = OAc (4) or Cl (5)]. Further treatment of compounds 4 or 5 with PPh3 in CH2Cl2 produced the bridge splitting and the formation of [Pd{kappa(2),C,N[1-{MeOe(CH2)(2)-}-3-(C6H4), 5-Ph-(C3HN2)]}X(PPh3)] [X = OAc (6) or Cl (7)]. The cytotoxic assessment of the free ligand (1) and the Pd(II) complexes on the two breast cancer cell lines MCF7 and MDA-MB231 reveals that: a) compound 1 is less active than its analogue [1-{Me2N-(CH2)(2)-}-3,5-Ph(2)e(C3HN2)] (Ic) and b) palladacycles 4-7 showed a remarkable cytotoxic activity in the MDA-MB231 cell line (with IC50 values in the range 9.1-14.4 mu M). (C) 2014 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.04.034
• 作为产物：
  描述：

  3,5-二苯基吡唑 、 2-氯乙基甲基醚 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以88%的产率得到1-(2-Methoxyethyl)-3,5-diphenylpyrazole
  参考文献：
  名称：

  Pd(II) complexes with N-substituted pyrazoles as ligands. The influence of the R group [OMe versus NMe2] of [1-{R–(CH2)2–}-3,5-Ph2–(C3HN2)] on their cytotoxic activity on breast cancer cell lines

  摘要：

  The study of the reactivity of the novel pyrazole derivative [1-{MeOe(CH2)(2)-}-3,5-PH2-(C3HN2)] (1) with Na-2[PdCl4] or Pd(OAc)(2) under different experimental conditions has allowed us to isolate and characterize the trans-isomers of [Pd{[1-{MeOe(CH2)(2)-}-3,5-PH2-(C3HN2)]}(2)(X)(2)] [X = Cl (2) or OAc (3)] and the di-m-ligand bridged cyclopalladated complexes [Pd{kappa(2),C,N[1-{MeOe(CH2)(2)-}-3-(C6H4), 5-Ph-(C3HN2)]}(mu-X)](2) [X = OAc (4) or Cl (5)]. Further treatment of compounds 4 or 5 with PPh3 in CH2Cl2 produced the bridge splitting and the formation of [Pd{kappa(2),C,N[1-{MeOe(CH2)(2)-}-3-(C6H4), 5-Ph-(C3HN2)]}X(PPh3)] [X = OAc (6) or Cl (7)]. The cytotoxic assessment of the free ligand (1) and the Pd(II) complexes on the two breast cancer cell lines MCF7 and MDA-MB231 reveals that: a) compound 1 is less active than its analogue [1-{Me2N-(CH2)(2)-}-3,5-Ph(2)e(C3HN2)] (Ic) and b) palladacycles 4-7 showed a remarkable cytotoxic activity in the MDA-MB231 cell line (with IC50 values in the range 9.1-14.4 mu M). (C) 2014 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.04.034

文献信息

• Pd(II) complexes with N-substituted pyrazoles as ligands. The influence of the R group [OMe versus NMe2] of [1-{R–(CH2)2–}-3,5-Ph2–(C3HN2)] on their cytotoxic activity on breast cancer cell lines
  作者：John U. Chukwu、Concepción López、Asensio González、Mercè Font-Bardía、M. Teresa Calvet、Ramon Messeguer、Carme Calvis

  DOI：10.1016/j.jorganchem.2014.04.034

  日期：2014.9

  The study of the reactivity of the novel pyrazole derivative [1-MeOe(CH2)(2)-}-3,5-PH2-(C3HN2)] (1) with Na-2[PdCl4] or Pd(OAc)(2) under different experimental conditions has allowed us to isolate and characterize the trans-isomers of [Pd[1-MeOe(CH2)(2)-}-3,5-PH2-(C3HN2)]}(2)(X)(2)] [X = Cl (2) or OAc (3)] and the di-m-ligand bridged cyclopalladated complexes [Pdkappa(2),C,N[1-MeOe(CH2)(2)-}-3-(C6H4), 5-Ph-(C3HN2)]}(mu-X)](2) [X = OAc (4) or Cl (5)]. Further treatment of compounds 4 or 5 with PPh3 in CH2Cl2 produced the bridge splitting and the formation of [Pdkappa(2),C,N[1-MeOe(CH2)(2)-}-3-(C6H4), 5-Ph-(C3HN2)]}X(PPh3)] [X = OAc (6) or Cl (7)]. The cytotoxic assessment of the free ligand (1) and the Pd(II) complexes on the two breast cancer cell lines MCF7 and MDA-MB231 reveals that: a) compound 1 is less active than its analogue [1-Me2N-(CH2)(2)-}-3,5-Ph(2)e(C3HN2)] (Ic) and b) palladacycles 4-7 showed a remarkable cytotoxic activity in the MDA-MB231 cell line (with IC50 values in the range 9.1-14.4 mu M). (C) 2014 Elsevier B. V. All rights reserved.