methyl 5-cyano-2-(2-{3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]phenyl}ethenyl)benzoate | 668262-61-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 5-cyano-2-(2-{3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]phenyl}ethenyl)benzoate
• 英文别名: Methyl 2-[2-[3-[(5-chloro-2,3-dihydroindol-1-yl)sulfonyl]phenyl]ethenyl]-5-cyanobenzoate
• CAS: 668262-61-1
• 化学式: C₂₅H₁₉ClN₂O₄S
• 分子量: 478.956
• InChiKey: ZTODDFKFLUAOOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 methyl 5-cyano-2-(2-{3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]phenyl}ethenyl)benzoate 在 tris-(dibenzylideneacetone)dipalladium(0) 臭氧 、 sodium hydroxide 作用下， 以6%的产率得到2-(2-{3-[(5-chloro-2,3-dihydro-1H-indol-1-yl)sulfonyl]phenyl}cyclopropyl)-5-cyanobenzoic acid
  参考文献：
  名称：

  [EN] ANTIBACTERIAL AGENTS
  [FR] AGENTS ANTIBACTERIENS

  摘要：

  公开号：

  WO2004018414A3
• 作为产物：
  描述：

  2-甲基-5-硝基苯甲酸甲酯 在 镍 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氢气 、 sodium hydride 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 生成 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

文献信息

• [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.