4-{ [ (4-CHLOROPHENYL) (methyl) amino] SULFONYL} benzoyl chloride | 666859-77-4

• 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-{ [ (4-CHLOROPHENYL) (methyl) amino] SULFONYL} benzoyl chloride
• 英文别名: 4-{[(4-chlorophenyl)(methyl)amino]sulfonyl}benzoyl chloride；4-{[(4-Chlorophenyl)(methyl)amino]sulfonyl}benzoyl chloride；4-[(4-chlorophenyl)-methylsulfamoyl]benzoyl chloride
• CAS: 666859-77-4
• 化学式: C₁₄H₁₁Cl₂NO₃S
• 分子量: 344.218
• InChiKey: WCAJXBUOYVEXRF-UHFFFAOYSA-N

物化性质

• 沸点：
  485.9±55.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{ [ (4-CHLOROPHENYL) (methyl) amino] SULFONYL} benzoyl chloride 在 吡啶 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 生成 N-[4-bromo-2-(1-hydroxyethyl)phenyl]-4-[(4-chlorophenyl)-methylsulfamoyl]benzamide
  参考文献：
  名称：

  Structure–activity relationships of bioisosteres of a carboxylic acid in a novel class of bacterial translation inhibitors

  摘要：

  The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents which suffered from extensive protein binding has been previously reported. The structure-activity relationships around the carboxylic acid substituent are described herein. This acid was replaced by several alternative functional groups in attempts to retain bioactivity while reducing protein binding. Only groups with an acidic proton retained activity, and analogs containing those groups maintained the protein binding inherent to this class of antibacterial agents. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.074
• 作为产物：
  描述：

  4-氯-N-甲基苯胺 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-{ [ (4-CHLOROPHENYL) (methyl) amino] SULFONYL} benzoyl chloride
  参考文献：
  名称：

  Structure–activity relationships of bioisosteres of a carboxylic acid in a novel class of bacterial translation inhibitors

  摘要：

  The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents which suffered from extensive protein binding has been previously reported. The structure-activity relationships around the carboxylic acid substituent are described herein. This acid was replaced by several alternative functional groups in attempts to retain bioactivity while reducing protein binding. Only groups with an acidic proton retained activity, and analogs containing those groups maintained the protein binding inherent to this class of antibacterial agents. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.074

文献信息

• Antibacterial benzoic acid derivatives
  申请人：——

  公开号：US20040142981A1

  公开（公告）日：2004-07-22

  The present invention relates to antibacterial agents that are useful for sterilization, sanitation, antisepsis, disinfection, and treatment of antibacterial infections in mammals.

  本发明涉及一种抗菌剂，可用于哺乳动物的消毒、卫生、消毒、抗菌感染的治疗。
• [EN] ANTIBACTERIAL BENZOIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDE BENZOIQUE ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2004018461A3

  公开（公告）日：2004-08-26
• Discovery and initial development of a novel class of antibacterials: Inhibitors of Staphylococcus aureus transcription/translation
  作者：Scott D. Larsen、Matthew R. Hester、J. Craig Ruble、Gregg M. Kamilar、Donna L. Romero、Brian Wakefield、Earline P. Melchior、Michael T. Sweeney、Keith R. Marotti

  DOI：10.1016/j.bmcl.2006.09.044

  日期：2006.12

  The novel bacterial transcription/translation (TT) inhibitor 1 was identified through a combination of high throughput screening and exploratory medicinal chemistry. Initial optimization of the anthranilic acid moiety and sulfonamide amine diversity was accomplished via 1- and two-dimensional solution phase libraries, resulting in an improvement in the MIC of the lead from 64 to 8 mu g/mL (compound 4I). Subsequent modification of the central aromatic ring and further refinement of the sulfonamide amines required the development of a solid phase route on Wang resin. The resulting libraries generated a number of potent antibacterials with MICs of <= 1 mu g/mL (e.g., 10b, 12, and 13). During the course of this work, it became apparent that the antibacterial activity of the series is not fully correlated with TT inhibition, suggesting that at least one additional mechanism of action is operative. (c) 2006 Elsevier Ltd. All rights reserved.
• Structure–activity relationships of bioisosteres of a carboxylic acid in a novel class of bacterial translation inhibitors
  作者：J. Craig Ruble、Brian D. Wakefield、Gregg M. Kamilar、Keith R. Marotti、Earline Melchior、Michael T. Sweeney、Gary E. Zurenko、Donna L. Romero

  DOI：10.1016/j.bmcl.2007.04.074

  日期：2007.7

  The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents which suffered from extensive protein binding has been previously reported. The structure-activity relationships around the carboxylic acid substituent are described herein. This acid was replaced by several alternative functional groups in attempts to retain bioactivity while reducing protein binding. Only groups with an acidic proton retained activity, and analogs containing those groups maintained the protein binding inherent to this class of antibacterial agents. (C) 2007 Elsevier Ltd. All rights reserved.