3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]benzaldehyde | 668262-55-3

• 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: 3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]benzaldehyde
• 英文别名: 3-[(5-chloro-2,3-dihydroindol-1-yl)sulfonyl]benzaldehyde
• CAS: 668262-55-3
• 化学式: C₁₅H₁₂ClNO₃S
• 分子量: 321.784
• InChiKey: OFXUQFWXHLFQIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  、 3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]benzaldehyde 在 sodium hydride 作用下， 以73%的产率得到methyl 5-cyano-2-(2-{3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]phenyl}ethenyl)benzoate
  参考文献：
  名称：

  Preparation of novel anthranilic acids as antibacterial agents. Extensive evaluation of alternative amide bioisosteres connecting the A- and the B-rings

  摘要：

  In the past few years, a significant effort has been devoted by Pharmacia toward the discovery of novel antibiotics. We have recently described the identification of an anthranilic acid lead 1 and the optimization resulting in the advanced lead 2. In this report, we describe the preparation of several selected amide bioisosteres connecting the A- and the B-rings. The E-alkene provided a rigid analog with equal potency to the corresponding amide. This indicates that the amide is not a recognition element rather acts as an appropriate spatial linker of the two important aryl A and B rings. The work here clearly demonstrates that the amide linker can be replaced with several functionalities without significant deterioration in the MIC activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.055
• 作为产物：
  描述：

  {3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]phenyl}methanol 在 pyridinium chlorochromate 作用下， 以100%的产率得到3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]benzaldehyde
  参考文献：
  名称：

  [EN] ANTIBACTERIAL AGENTS
  [FR] AGENTS ANTIBACTERIENS

  摘要：

  公开号：

  WO2004018414A3

文献信息

• Antibacterial agents
  申请人：Thorarensen Atli

  公开号：US20050113450A1

  公开（公告）日：2005-05-26

  The present invention relates to antibacterial agents that are useful for sterilization, sanitation, antisepsis, and disinfection

  本发明涉及用于杀菌、卫生、消毒和消毒的抗菌剂。
• [EN] ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2004018414A3

  公开（公告）日：2004-06-17
• Preparation of novel anthranilic acids as antibacterial agents. Extensive evaluation of alternative amide bioisosteres connecting the A- and the B-rings
  作者：Atli Thorarensen、Brian D. Wakefield、Donna L. Romero、Keith R. Marotti、Michael T. Sweeney、Gary E. Zurenko、Douglas C. Rohrer、Fusen Han、Garold L. Bryant

  DOI：10.1016/j.bmcl.2007.02.055

  日期：2007.5

  In the past few years, a significant effort has been devoted by Pharmacia toward the discovery of novel antibiotics. We have recently described the identification of an anthranilic acid lead 1 and the optimization resulting in the advanced lead 2. In this report, we describe the preparation of several selected amide bioisosteres connecting the A- and the B-rings. The E-alkene provided a rigid analog with equal potency to the corresponding amide. This indicates that the amide is not a recognition element rather acts as an appropriate spatial linker of the two important aryl A and B rings. The work here clearly demonstrates that the amide linker can be replaced with several functionalities without significant deterioration in the MIC activity. (c) 2007 Elsevier Ltd. All rights reserved.