4-(octyloxy)phenyl isonicotinate | 319430-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(octyloxy)phenyl isonicotinate
• 英文别名: 4-(Octyloxy)phenyl pyridine-4-carboxylate；(4-octoxyphenyl) pyridine-4-carboxylate
• CAS: 319430-12-1
• 化学式: C₂₀H₂₅NO₃
• mdl: MFCD00984211
• 分子量: 327.423
• InChiKey: LJAINZKGSGJYOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 4-(octyloxy)phenyl isonicotinate 以 二氯甲烷 为溶剂， 反应 3.0h， 以99%的产率得到
  参考文献：
  名称：

  Arene ruthenium dichloro complexes containing isonicotinic ester ligands: Synthesis, molecular structure and cytotoxicity

  摘要：

  A series of p-cymene ruthenium dichloro complexes containing isonicotinic ester ligands, [(arene) RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)(n)-CH3] (n = 1: 1, n = 3: 2, n = 5: 3, n = 7:4, n = 9: 5, n = 11: 6, n = 13: 7, n = 15: 8), were prepared from p-cymene ruthenium dichloro dimer and the corresponding isonicotinic ester ligand. The single-crystal X-ray analysis of 1 shows the molecule to adopt the usual pseudo-tetrahedral piano-stool geometry, the isonicotinic ester ligand being coordinated through the nitrogen atom. The cytotoxicity of all complexes and of the free ligands was studied towards human ovarian cancer cells; high activities were observed only for n = 9 (presenting a chain with ten carbon atoms), both as far as the free ligands and the complexes are concerned. Based on this result, a new isonicotinic ester ligand with a C-10 substituent containing a terminal alcohol function, NC5H4-4-COO-C6H4-p-O-(CH2)(10)-OH, was synthesized by a four-step method, and arene ruthenium complexes thereof, [(arene)RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)(10)-OH] (arene = C6H6: 9a, arene = p-MeC6H4Pri: 9b, arene = C6Me6: 9c) were prepared. The complexes 9a and 9b show indeed remarkable anticancer activities, the IC50 values for human ovarian cancer cells being in the submicromolar range. The highest cytotoxicity was observed for complex 9b, with IC50 values of 0.18 mu M for A2780 and 3.04 mu M for the cisplatin-resistant mutant A2780cisR. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.10.016
• 作为产物：
  描述：

  1-(苄氧基)-4-(辛氧基)苯 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 生成 4-(octyloxy)phenyl isonicotinate
  参考文献：
  名称：

  Arene ruthenium dichloro complexes containing isonicotinic ester ligands: Synthesis, molecular structure and cytotoxicity

  摘要：

  A series of p-cymene ruthenium dichloro complexes containing isonicotinic ester ligands, [(arene) RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)(n)-CH3] (n = 1: 1, n = 3: 2, n = 5: 3, n = 7:4, n = 9: 5, n = 11: 6, n = 13: 7, n = 15: 8), were prepared from p-cymene ruthenium dichloro dimer and the corresponding isonicotinic ester ligand. The single-crystal X-ray analysis of 1 shows the molecule to adopt the usual pseudo-tetrahedral piano-stool geometry, the isonicotinic ester ligand being coordinated through the nitrogen atom. The cytotoxicity of all complexes and of the free ligands was studied towards human ovarian cancer cells; high activities were observed only for n = 9 (presenting a chain with ten carbon atoms), both as far as the free ligands and the complexes are concerned. Based on this result, a new isonicotinic ester ligand with a C-10 substituent containing a terminal alcohol function, NC5H4-4-COO-C6H4-p-O-(CH2)(10)-OH, was synthesized by a four-step method, and arene ruthenium complexes thereof, [(arene)RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)(10)-OH] (arene = C6H6: 9a, arene = p-MeC6H4Pri: 9b, arene = C6Me6: 9c) were prepared. The complexes 9a and 9b show indeed remarkable anticancer activities, the IC50 values for human ovarian cancer cells being in the submicromolar range. The highest cytotoxicity was observed for complex 9b, with IC50 values of 0.18 mu M for A2780 and 3.04 mu M for the cisplatin-resistant mutant A2780cisR. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.10.016

文献信息

• Arene ruthenium dichloro complexes containing isonicotinic ester ligands: Synthesis, molecular structure and cytotoxicity
  作者：Farooq-Ahmad Khan、Bruno Therrien、Georg Süss-Fink、Olivier Zava、Paul J. Dyson

  DOI：10.1016/j.jorganchem.2012.10.016

  日期：2013.4

  A series of p-cymene ruthenium dichloro complexes containing isonicotinic ester ligands, [(arene) RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)(n)-CH3] (n = 1: 1, n = 3: 2, n = 5: 3, n = 7:4, n = 9: 5, n = 11: 6, n = 13: 7, n = 15: 8), were prepared from p-cymene ruthenium dichloro dimer and the corresponding isonicotinic ester ligand. The single-crystal X-ray analysis of 1 shows the molecule to adopt the usual pseudo-tetrahedral piano-stool geometry, the isonicotinic ester ligand being coordinated through the nitrogen atom. The cytotoxicity of all complexes and of the free ligands was studied towards human ovarian cancer cells; high activities were observed only for n = 9 (presenting a chain with ten carbon atoms), both as far as the free ligands and the complexes are concerned. Based on this result, a new isonicotinic ester ligand with a C-10 substituent containing a terminal alcohol function, NC5H4-4-COO-C6H4-p-O-(CH2)(10)-OH, was synthesized by a four-step method, and arene ruthenium complexes thereof, [(arene)RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)(10)-OH] (arene = C6H6: 9a, arene = p-MeC6H4Pri: 9b, arene = C6Me6: 9c) were prepared. The complexes 9a and 9b show indeed remarkable anticancer activities, the IC50 values for human ovarian cancer cells being in the submicromolar range. The highest cytotoxicity was observed for complex 9b, with IC50 values of 0.18 mu M for A2780 and 3.04 mu M for the cisplatin-resistant mutant A2780cisR. (C) 2012 Elsevier B.V. All rights reserved.