NCS 273905

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: NCS 273905
• 英文别名: N-[2-[2-(8-quinolylsulfonylamino)ethyldisulfanyl]ethyl]quinoline-8-sulfonamide；N-[2-[2-(quinolin-8-ylsulfonylamino)ethyldisulfanyl]ethyl]quinoline-8-sulfonamide
• 化学式: C₂₂H₂₂N₄O₄S₄
• 分子量: 534.705
• InChiKey: NPEZKTHSFUYYQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  186
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,3'-二硝基二苯二硫醚 、 NCS 273905 在 1,4-二巯基-2,3-丁二醇 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 12.0h， 生成 N-[2-[(3-nitrophenyl)disulfanyl]ethyl]quinoline-8-sulfonamide
  参考文献：
  名称：

  Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)

  摘要：

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.

  DOI：

  10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3

文献信息

• Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)
  作者：K. C. Nicolaou、Robert Hughes、Jeffrey A. Pfefferkorn、Sofia Barluenga、A. J. Roecker

  DOI：10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3

  日期：2001.10.1

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.