(E)-N'-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide | 1453354-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N'-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide
• 英文别名: N-[(E)-1-(5-bromo-2-hydroxyphenyl)ethylideneamino]-3-hydroxynaphthalene-2-carboxamide
• CAS: 1453354-72-7
• 化学式: C₁₉H₁₅BrN₂O₃
• 分子量: 399.244
• InChiKey: WAOUCRRLHSKQCV-SRZZPIQSSA-N

物化性质

• 熔点：
  214-216 °C
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  (E)-N'-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide 、 二苯基氧化锡 以 甲苯 为溶剂， 以73%的产率得到{[1-(5-bromo-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}diphenyltin(IV)
  参考文献：
  名称：

  Synthesis, characterization and biological activity of diorganotin complexes with ONO terdentate Schiff base

  摘要：

  Diorganotin(IV) complexes with general formula R2SnL [H2L = (E)-N'-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H2L1) and (E)-N'-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H2L2); R = Me, Bu, Ph, Cy, Bz, o-ClBz and p-ClBz (1-14)] have been synthesized and characterized by IR, H-1, C-13 and Sn-119 NMR spectroscopic techniques and single crystal Xray diffractometry. The structure of the complexes, {[1-(5-bromo-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 1, {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 8 and {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dicyclohexyltin(IV), 11 reveals a five-coordinated, trigonal-bipyramidal geometry, whereby the trigonal plane of the complexes consists of the imine nitrogen atom and alkyl groups from the diorganotin moieties. The complexes are stabilized by a strong intramolecular hydrogen bonding between N(2) and O(3)-H(3). The Schiff bases and their corresponding diorganotin(IV) complexes have been evaluated against three human carcinoma cell lines, namely HT29 (human colon carcinoma cell line), SKOV-3 (human ovarian cancer cell line) and MCF7 (hormone-dependent breast carcinoma cell line), for their cytotoxic activities. The dimethyltin derivatives and dibutyltin derivatives of the Schiff base ligands display good cytotoxic activities against the tested cell lines. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.04.036
• 作为产物：
  描述：

  1-(3-溴苯基)-2-羟基乙酮 、 3-羟基-2-萘酸肼 以 甲醇 为溶剂， 反应 2.0h， 以72%的产率得到(E)-N'-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide
  参考文献：
  名称：

  Synthesis, characterization and biological activity of diorganotin complexes with ONO terdentate Schiff base

  摘要：

  Diorganotin(IV) complexes with general formula R2SnL [H2L = (E)-N'-[1-(5-bromo-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H2L1) and (E)-N'-[1-(5-chloro-2-hydroxyphenyl)ethylidene]-3-hydroxy-2-naphthohydrazide (H2L2); R = Me, Bu, Ph, Cy, Bz, o-ClBz and p-ClBz (1-14)] have been synthesized and characterized by IR, H-1, C-13 and Sn-119 NMR spectroscopic techniques and single crystal Xray diffractometry. The structure of the complexes, {[1-(5-bromo-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 1, {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dimethyltin(IV), 8 and {[1-(5-chloro-2-oxidophenyl)ethylidene]-3-hydroxy-2-naphthohydrazidato}dicyclohexyltin(IV), 11 reveals a five-coordinated, trigonal-bipyramidal geometry, whereby the trigonal plane of the complexes consists of the imine nitrogen atom and alkyl groups from the diorganotin moieties. The complexes are stabilized by a strong intramolecular hydrogen bonding between N(2) and O(3)-H(3). The Schiff bases and their corresponding diorganotin(IV) complexes have been evaluated against three human carcinoma cell lines, namely HT29 (human colon carcinoma cell line), SKOV-3 (human ovarian cancer cell line) and MCF7 (hormone-dependent breast carcinoma cell line), for their cytotoxic activities. The dimethyltin derivatives and dibutyltin derivatives of the Schiff base ligands display good cytotoxic activities against the tested cell lines. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.04.036