4-methyl-[1,2,3]thiadiazole-5-carboxylic acid (5-bromo-2-hydroxybenzylidene)hydrazide | 351327-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid (5-bromo-2-hydroxybenzylidene)hydrazide
• 英文别名: ME0167；N-[(5-bromo-2-hydroxyphenyl)methylideneamino]-4-methylthiadiazole-5-carboxamide
• CAS: 351327-87-2
• 化学式: C₁₁H₉BrN₄O₂S
• 分子量: 341.188
• InChiKey: RRYHYBRJBYHZIG-UHFFFAOYSA-N

物化性质

• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-溴水杨醛 、 4-甲基-1,2,3-噻二唑-5-羧酸酰肼 以 乙醇 为溶剂， 生成 4-methyl-[1,2,3]thiadiazole-5-carboxylic acid (5-bromo-2-hydroxybenzylidene)hydrazide
  参考文献：
  名称：

  Statistical molecular design of a focused salicylidene acylhydrazide library and multivariate QSAR of inhibition of type III secretion in the Gram-negative bacterium Yersinia

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2010.02.022

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.