2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone | 541517-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone
• 英文别名: 5-chloro-2-hydroxy-N-[(2-hydroxynaphthalen-1-yl)methylideneamino]benzamide
• CAS: 541517-01-5
• 化学式: C₁₈H₁₃ClN₂O₃
• 分子量: 340.766
• InChiKey: XKYSRSBJVKNLAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone 、 二苯基二氯化锡 在 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.0h， 以83%的产率得到
  参考文献：
  名称：

  Di- and tri-organotin(IV) complexes with 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone: Synthesis, characterization and in vitro antitumor activities

  摘要：

  Series of new organotin(IV) complexes of the types R2SnL, R is Me (1), Ph (2), o-CleC(6)H(4)CH(2) (3); and [R3SnL](infinity), R = n-Bu (4) (H2L = 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone) have been synthesized and structurally characterized by means of elemental analysis, FT-IR, UV-vis spectroscopy, NMR (H-1, C-13 and Sn-119) spectra and X-ray single crystal diffraction analyses. Structural analyses reveal that complexes 1-3 show similar monomeric structure, in which the tin center is coordinated with the enolic tridentate ligand (L) in the ONO chelate mode and exhibits five-coordinated trigonal bipyramidal geometry. Unexpectedly, complex 4 presents as a rare one-dimensional chain polymeric structure, in which the coordination of Sn is also five-coordinated trigonal bipyramidal geometry and the segment of tri-n-butyltin is bridged by the de-protonated phenolate O atom and the carbonyl O atom from the non-enolic Schiff base ligand. All compounds exhibit good in vitro antitumor activity toward human colon cancer cells (HCT-8), lung cancer cells (A549) and human promyelocyticfina leukemic cells (HL-60). The results indicate that both alkyl groups bound with tin centers and the structural of organotin compounds have significant effect on their in vitro antitumor activities. Among them, the polymeric tri-n-butyltin Schiff base complex 4 is the most active one, and the complex 3 shows high selectivity on the tumor cells HCT-8 and HL-60. For all of the title compounds, there was a good dose-effect relationship. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.10.031
• 作为产物：
  描述：

  5-氯-2-羟基苯甲酰肼 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone
  参考文献：
  名称：

  Di- and tri-organotin(IV) complexes with 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone: Synthesis, characterization and in vitro antitumor activities

  摘要：

  Series of new organotin(IV) complexes of the types R2SnL, R is Me (1), Ph (2), o-CleC(6)H(4)CH(2) (3); and [R3SnL](infinity), R = n-Bu (4) (H2L = 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone) have been synthesized and structurally characterized by means of elemental analysis, FT-IR, UV-vis spectroscopy, NMR (H-1, C-13 and Sn-119) spectra and X-ray single crystal diffraction analyses. Structural analyses reveal that complexes 1-3 show similar monomeric structure, in which the tin center is coordinated with the enolic tridentate ligand (L) in the ONO chelate mode and exhibits five-coordinated trigonal bipyramidal geometry. Unexpectedly, complex 4 presents as a rare one-dimensional chain polymeric structure, in which the coordination of Sn is also five-coordinated trigonal bipyramidal geometry and the segment of tri-n-butyltin is bridged by the de-protonated phenolate O atom and the carbonyl O atom from the non-enolic Schiff base ligand. All compounds exhibit good in vitro antitumor activity toward human colon cancer cells (HCT-8), lung cancer cells (A549) and human promyelocyticfina leukemic cells (HL-60). The results indicate that both alkyl groups bound with tin centers and the structural of organotin compounds have significant effect on their in vitro antitumor activities. Among them, the polymeric tri-n-butyltin Schiff base complex 4 is the most active one, and the complex 3 shows high selectivity on the tumor cells HCT-8 and HL-60. For all of the title compounds, there was a good dose-effect relationship. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.10.031