phenylacetic acid (5-bromo-2-hydroxy-3-methoxybenzylidene)hydrazide | 330571-30-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: phenylacetic acid (5-bromo-2-hydroxy-3-methoxybenzylidene)hydrazide
• 英文别名: ME0262；N-[(5-bromo-2-hydroxy-3-methoxyphenyl)methylideneamino]-2-phenylacetamide
• CAS: 330571-30-7
• 化学式: C₁₆H₁₅BrN₂O₃
• 分子量: 363.211
• InChiKey: DFEGEZBMCZQZCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  V(acac)3 、 phenylacetic acid (5-bromo-2-hydroxy-3-methoxybenzylidene)hydrazide 以 乙醇 为溶剂， 反应 0.42h， 以0.487 g的产率得到
  参考文献：
  名称：

  V(III) 和 V(IV) 席夫碱复合物作为潜在的胰岛素模拟化合物 – 比较、表征和生物活性

  摘要：

  DOI：

  10.1016/j.poly.2022.115682
• 作为产物：
  描述：

  5-溴-2-羟基-3-甲氧基苯甲醛 、 苯乙酸肼 以 乙醇 为溶剂， 反应 0.17h， 生成 phenylacetic acid (5-bromo-2-hydroxy-3-methoxybenzylidene)hydrazide
  参考文献：
  名称：

  [EN] VANADIUM COMPLEXES WITH HYDRAZIDE-HYDRAZONES, PROCESS FOR THEIR PREPARATION, PHARMACEUTICAL FORMULATIONS AND THE USE OF THEREOF.
  [FR] COMPLEXES DU VANADIUM AVEC DES HYDRAZIDE-HYDRAZONES, LEUR PROCÉDÉ DE PRÉPARATION, FORMULATIONS PHARMACEUTIQUES ET LEUR UTILISATION

  摘要：

  通用公式为M[VX(ONO)y(L)n]-mS的钒配合物，其中X为氧或不存在，L为L1或L2，其中Li代表卤素阴离子或中性分子或脱质子溶剂，该溶剂选自包括C1-C12醇类和/或水的组，L2为中性或带负电荷的NN、NO或OO-给体配体，选自以下组：多吡啶、1,10-邻菲啰啉、吡喁酮、喹啉或吡啶羧酸，S为选自C1-C4醇类、水或硫酸的中性溶剂分子，M可能不存在，若存在，则为带单电荷的碱金属阳离子、铵阳离子、烷基铵阳离子，字母O和N代表配体与钒结合的原子。该发明还包括制备钒配合物的方法、含有这些配合物的药物制剂以及这些配合物的用途。

  公开号：

  WO2014073992A1

文献信息

• Statistical molecular design of a focused salicylidene acylhydrazide library and multivariate QSAR of inhibition of type III secretion in the Gram-negative bacterium Yersinia
  作者：Markus K. Dahlgren、Caroline E. Zetterström、Åsa Gylfe、Anna Linusson、Mikael Elofsson

  DOI：10.1016/j.bmc.2010.02.022

  日期：2010.4

  A combined application of statistical molecular design (SMD), quantitative structure-activity relationship (QSAR) modeling and prediction of new active compounds was effectively used to develop salicylidene acylhydrazides as inhibitors of type III secretion (T3S) in the Gram-negative pathogen Yersinia pseudotuberculosis. SMD and subsequent synthesis furnished 50 salicylidene acylhydrazides in high purity. Based on data from biological evaluation in T3S linked assays 18 compounds were classified as active and 25 compounds showed a dose-dependent inhibition. The 25 compounds were used to compute two multivariate QSAR models and two multivariate discriminant analysis models were computed from both active and inactive compounds. Three of the models were used to predict 4416 virtual compounds in consensus and eight new compounds were selected as an external test set. Synthesis and biological evaluation of the test set in Y. pseudotuberculosis and the intracellular pathogen Chlamydia trachomatis validated the models. Y. pseudotuberculosis and C. trachomatis cell-based infection models showed that compounds identified in this study are selective and non-toxic inhibitors of T3S dependent virulence. (C) 2010 Elsevier Ltd. All rights reserved.