4-Chloro-N-(3-chloro-4-fluoro-phenyl)-2-nitro-benzamide | 330215-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Chloro-N-(3-chloro-4-fluoro-phenyl)-2-nitro-benzamide
• 英文别名: 4-chloro-N-(3-chloro-4-fluorophenyl)-2-nitrobenzamide
• CAS: 330215-58-2
• 化学式: C₁₃H₇Cl₂FN₂O₃
• mdl: MFCD01215422
• 分子量: 329.115
• InChiKey: OOSJRIOKOUDGAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Chloro-N-(3-chloro-4-fluoro-phenyl)-2-nitro-benzamide 在 palladium on activated charcoal 三氯化铁 、 甲烷 、 一水合肼 作用下， 以 甲醇 为溶剂， 生成 2-amino-4-chloro-N-(3-chloro-4-fluorophenyl)benzamide
  参考文献：
  名称：

  Inhibitors of type III secretion in Yersinia: Design, synthesis and multivariate QSAR of 2-arylsulfonylamino-benzanilides

  摘要：

  Compound 1, 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-N-(3,4-dichloro-phenyl)-benzamide. was identified as a putative type III secretion inhibitor in Yersinia. and the compound thus has a potential to be used to prevent or treat bacterial infections. A set of seven analogues was svnthesized and evaluated in a type III secretion dependent reporter-gene assay with viable bacterial to give basic SAR. A second set of 19 compounds was obtained by statistical molecular design in the building block and product space and by subsequent synthesis. Evaluation in the reporter-gene assay showed that the compounds ranged from nonactive to compounds more potent than 1. Based on the data multivariate QSAR models were established and the final Hi-PLS model showed good correlation between experimentally determined % inhibition and the calculated % inhibition of the reporter-gene signal. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.047
• 作为产物：
  描述：

  3-氯-4-氟苯胺 、 4-氯-2-硝基苯甲酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-Chloro-N-(3-chloro-4-fluoro-phenyl)-2-nitro-benzamide
  参考文献：
  名称：

  Inhibitors of type III secretion in Yersinia: Design, synthesis and multivariate QSAR of 2-arylsulfonylamino-benzanilides

  摘要：

  Compound 1, 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-N-(3,4-dichloro-phenyl)-benzamide. was identified as a putative type III secretion inhibitor in Yersinia. and the compound thus has a potential to be used to prevent or treat bacterial infections. A set of seven analogues was svnthesized and evaluated in a type III secretion dependent reporter-gene assay with viable bacterial to give basic SAR. A second set of 19 compounds was obtained by statistical molecular design in the building block and product space and by subsequent synthesis. Evaluation in the reporter-gene assay showed that the compounds ranged from nonactive to compounds more potent than 1. Based on the data multivariate QSAR models were established and the final Hi-PLS model showed good correlation between experimentally determined % inhibition and the calculated % inhibition of the reporter-gene signal. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.047

文献信息

• Synthesis of quinazolin-4(3 H )-ones and 1,2-dihydroquinazolin-4(3 H )-ones with the aid of a low-valent titanium reagent
  作者：Daqing Shi、Liangce Rong、Juxian Wang、Qiya Zhuang、Xiangshan Wang、Hongwen Hu

  DOI：10.1016/s0040-4039(03)00449-0

  日期：2003.4

  A short and facile synthesis of a series of quinazolin-4(3H)-ones and 1,2-dihydroquinazolin-4(3H)-ones was accomplished in good yields via the novel reductive cyclization of o-nitrobenzamides and triethyl orthoformate, aldehydes or ketones promoted by TiCl4/Zn.

  一系列喹唑啉-4-的短而简便合成（3 ħ） -酮和1,2-二氢喹唑啉-4（3 H ^） -酮在良好的产率通过的新颖还原性环化完成ö -nitrobenzamides和原甲酸三乙酯， TiCl 4 / Zn促进的醛或酮。
• Facile Synthesis of Substituted Quinazolin‐4‐(3H)‐ones Using Low‐Valence Titanium Reagent
  作者：Daqing Shi、Liangce Rong、Juxian Wang、Qiya Zhuang、Xiangshan Wang、Hongwen Hu

  DOI：10.1081/scc-120034156

  日期：2004.12.31

  Abstract A short and facile synthesis of a series of 3‐aryl quinazolin‐4‐(3H)‐ones was accomplished in good yields via the intermolecular reductive coupling reaction of N‐aryl‐2‐nitrobenzamide and triethyl orthoformate promoted by TiCl4/Zn.

  摘要 通过 TiCl4/Zn 促进的 N-芳基-2-硝基苯甲酰胺和原甲酸三乙酯的分子间还原偶联反应，以良好的收率快速简便地合成了一系列 3-芳基喹唑啉-4-(3H)-酮。
• Shi, Daqing; Rong, Liangce; Wang, Juxian, Journal of Chemical Research - Part S, 2003, # 6, p. 366 - 367
  作者：Shi, Daqing、Rong, Liangce、Wang, Juxian、Zhuang, Qiya、Hu, Hongwen

  DOI：——

  日期：——
• Inhibitors of type III secretion in Yersinia: Design, synthesis and multivariate QSAR of 2-arylsulfonylamino-benzanilides
  作者：Anna M. Kauppi、C. David Andersson、Henrik A. Norberg、Charlotta Sundin、Anna Linusson、Mikael Elofsson

  DOI：10.1016/j.bmc.2007.07.047

  日期：2007.11

  Compound 1, 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-N-(3,4-dichloro-phenyl)-benzamide. was identified as a putative type III secretion inhibitor in Yersinia. and the compound thus has a potential to be used to prevent or treat bacterial infections. A set of seven analogues was svnthesized and evaluated in a type III secretion dependent reporter-gene assay with viable bacterial to give basic SAR. A second set of 19 compounds was obtained by statistical molecular design in the building block and product space and by subsequent synthesis. Evaluation in the reporter-gene assay showed that the compounds ranged from nonactive to compounds more potent than 1. Based on the data multivariate QSAR models were established and the final Hi-PLS model showed good correlation between experimentally determined % inhibition and the calculated % inhibition of the reporter-gene signal. (C) 2007 Elsevier Ltd. All rights reserved.