N-(4-chlorophenyl)-2-hydroxy-5-iodobenzamide | 7103-96-0

• 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: N-(4-chlorophenyl)-2-hydroxy-5-iodobenzamide
• CAS: 7103-96-0
• 化学式: C₁₃H₉ClINO₂
• mdl: MFCD18428436
• 分子量: 373.577
• InChiKey: HXDYOSSLXZJTCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-2-hydroxy-5-iodobenzamide 、 乙酸酐 在 磷酸 作用下， 反应 1.0h， 生成 Acetic acid 2-(4-chloro-phenylcarbamoyl)-4-iodo-phenyl ester
  参考文献：
  名称：

  水杨酰苯胺的设计，合成和多变量定量结构-活性关系-耶尔森菌中III型分泌的强效抑制剂。

  摘要：

  选择，合成和在三个循环中生物学评估水杨酰苯胺N-（4-氯苯基）-2-乙酰氧基-3,5-二碘联苯甲酰胺1a的类似物，后者是耶尔森氏菌III型分泌（T3S）的抑制剂。首先，合成一组在水杨酸环部分具有变化的类似物以探测可能的结构变化。建立了基本的结构-活性关系，然后将其用于从水杨酰苯胺的主成分分析得分图中挑选出化合物，以生成第二组。使用D-最佳洋葱设计设计了第三组具有增加的生物活性的生物活性。使用与T3S抑制百分比相关的构件的PLS评分矢量，计算了使用层次化部分最小二乘回归到潜在结构（Hi-PLS）的定量构效关系模型。使用与Hi-PLS模型相同的描述符集导出PLS判别分析（PLS-DA）模型。两种模型均通过外部测试仪进行了验证。

  DOI：

  10.1021/jm070741b
• 作为产物：
  描述：

  5-碘水杨酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(4-chlorophenyl)-2-hydroxy-5-iodobenzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activities of Closantel Analogues: Structural Promiscuity and Its Impact on Onchocerca volvulus

  摘要：

  Onchocerciasis, or river blindness, is a neglected tropical disease that affects more than 37 million people worldwide, primarily in Africa and Central and South America. We have disclosed evidence that the larval-stage-specific chitinase, OvCHT1, may be a potential biological target for affecting nematode development. On the basis of screening efforts, closantel, a known anthelmintic drug, was discovered as a potent and highly specific OvCHT1 inhibitor. Originally, closantel's anthelmintic mode of action was believed to rely solely on its role as a proton ionophore; thus, the impact of each of its biological activities on O. volvulus L3 molting was investigated. Structure activity relationship studies on an active closantel fragment are detailed, and remarkably, by use of a simple salicylanilide scaffold, compounds acting only as protonophores or chitinase inhibitors were identified. From these data, unexpected synergistic protonophore and chitinase inhibition activities have also been found to be critical for molting in O. volvulus L3 larvae.

  DOI：

  10.1021/jm200364n

文献信息

• Synthesis and antiproliferative activities against Hep-G2 of salicylanide derivatives: potent inhibitors of the epidermal growth factor receptor (EGFR) tyrosine kinase
  作者：Zhen-Wei Zhu、Lei Shi、Xiao-Ming Ruan、Ying Yang、Huan-Qiu Li、Suo-Ping Xu、Hai-Liang Zhu

  DOI：10.3109/14756361003671060

  日期：2011.2.1

  A series of salicylanilide derivatives (compounds 1--32) were synthesised by reacting substituted salicylic acids and anilines. The chemical structures of these compounds were determined by
• US7351861B2
  申请人：——

  公开号：US7351861B2

  公开（公告）日：2008-04-01
• Design, Synthesis, and Multivariate Quantitative Structure−Activity Relationship of SalicylanilidesPotent Inhibitors of Type III Secretion in <i>Yersinia</i>
  作者：Markus K. Dahlgren、Anna M. Kauppi、Ing-Marie Olsson、Anna Linusson、Mikael Elofsson

  DOI：10.1021/jm070741b

  日期：2007.11.1

  possible structural variation. A basic structure-activity relationship was established and then used to cherry-pick compounds from a principal component analysis score plot of salicylanilides to generate a second set. A third set with increased likelihood of biological activity was designed using D-optimal onion design. A quantitative structure-activity relationship model using hierarchical partial least-square

  选择，合成和在三个循环中生物学评估水杨酰苯胺N-（4-氯苯基）-2-乙酰氧基-3,5-二碘联苯甲酰胺1a的类似物，后者是耶尔森氏菌III型分泌（T3S）的抑制剂。首先，合成一组在水杨酸环部分具有变化的类似物以探测可能的结构变化。建立了基本的结构-活性关系，然后将其用于从水杨酰苯胺的主成分分析得分图中挑选出化合物，以生成第二组。使用D-最佳洋葱设计设计了第三组具有增加的生物活性的生物活性。使用与T3S抑制百分比相关的构件的PLS评分矢量，计算了使用层次化部分最小二乘回归到潜在结构（Hi-PLS）的定量构效关系模型。使用与Hi-PLS模型相同的描述符集导出PLS判别分析（PLS-DA）模型。两种模型均通过外部测试仪进行了验证。
• Design, Synthesis, and Biological Activities of Closantel Analogues: Structural Promiscuity and Its Impact on <i>Onchocerca volvulus</i>
  作者：Amanda L. Garner、Christian Gloeckner、Nancy Tricoche、Joseph S. Zakhari、Moses Samje、Fidelis Cho-Ngwa、Sara Lustigman、Kim D. Janda

  DOI：10.1021/jm200364n

  日期：2011.6.9

  Onchocerciasis, or river blindness, is a neglected tropical disease that affects more than 37 million people worldwide, primarily in Africa and Central and South America. We have disclosed evidence that the larval-stage-specific chitinase, OvCHT1, may be a potential biological target for affecting nematode development. On the basis of screening efforts, closantel, a known anthelmintic drug, was discovered as a potent and highly specific OvCHT1 inhibitor. Originally, closantel's anthelmintic mode of action was believed to rely solely on its role as a proton ionophore; thus, the impact of each of its biological activities on O. volvulus L3 molting was investigated. Structure activity relationship studies on an active closantel fragment are detailed, and remarkably, by use of a simple salicylanilide scaffold, compounds acting only as protonophores or chitinase inhibitors were identified. From these data, unexpected synergistic protonophore and chitinase inhibition activities have also been found to be critical for molting in O. volvulus L3 larvae.