(5S)-5-[[(4-ethyl-1,1-dioxo-1lambda6,2,4-benzothiadiazin-3-ylidene)amino]methyl]-3-(3-fluoro-4-piperazin-1-ylphenyl)-1,3-oxazolidin-2-one | 1280555-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (5S)-5-[[(4-ethyl-1,1-dioxo-1lambda6,2,4-benzothiadiazin-3-ylidene)amino]methyl]-3-(3-fluoro-4-piperazin-1-ylphenyl)-1,3-oxazolidin-2-one
• 英文别名: (5S)-5-[[(4-ethyl-1,1-dioxo-1λ6,2,4-benzothiadiazin-3-ylidene)amino]methyl]-3-(3-fluoro-4-piperazin-1-ylphenyl)-1,3-oxazolidin-2-one
• CAS: 1280555-57-8
• 化学式: C₂₃H₂₇FN₆O₄S
• 分子量: 502.57
• InChiKey: DKTKPHHYMZAMGY-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(5-(4-氯苯基)-呋喃-2-基)-丙烯酸 、 (5S)-5-[[(4-ethyl-1,1-dioxo-1lambda6,2,4-benzothiadiazin-3-ylidene)amino]methyl]-3-(3-fluoro-4-piperazin-1-ylphenyl)-1,3-oxazolidin-2-one 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以64%的产率得到(5S)-3-[4-[4-[(E)-3-[5-(4-chlorophenyl)furan-2-yl]prop-2-enoyl]piperazin-1-yl]-3-fluorophenyl]-5-[[(4-ethyl-1,1-dioxo-1lambda6,2,4-benzothiadiazin-3-ylidene)amino]methyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Anti-tubercular agents. Part 6: Synthesis and antimycobacterial activity of novel arylsulfonamido conjugated oxazolidinones

  摘要：

  As a part of investigation of new anti-tubercular agents in this laboratory, herein we describe the synthesis of a new class of arylsulfonamido conjugated oxazolidinones. The in vitro activity of these conjugated (6a-f, 7a-d, 9a-c and 11a-c) molecules against Mycobacterium tuberculosis H(37)Rv by using rifampicin and linezolide as positive controls is discussed, compounds 7c and 9a-c are found to be the most active members in this series. Further, cytotoxicity of the potent conjugates of the series (7c, and 9a-c) was evaluated on human foreskin fibroblast (HFF) cells by using MTT assay. Finally, these studies suggest that compounds 7c and 9a may serve as promising lead scaffolds for further generation of new as anti-TB agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.028
• 作为产物：
  描述：

  (S)-N-(3-(3-fluoro-4-((N-4-carbobenzoxy)piperazin-1-yl)phenyl)-2-oxo-oxazolidin-5-yl)methylamine 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (5S)-5-[[(4-ethyl-1,1-dioxo-1lambda6,2,4-benzothiadiazin-3-ylidene)amino]methyl]-3-(3-fluoro-4-piperazin-1-ylphenyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Anti-tubercular agents. Part 6: Synthesis and antimycobacterial activity of novel arylsulfonamido conjugated oxazolidinones

  摘要：

  As a part of investigation of new anti-tubercular agents in this laboratory, herein we describe the synthesis of a new class of arylsulfonamido conjugated oxazolidinones. The in vitro activity of these conjugated (6a-f, 7a-d, 9a-c and 11a-c) molecules against Mycobacterium tuberculosis H(37)Rv by using rifampicin and linezolide as positive controls is discussed, compounds 7c and 9a-c are found to be the most active members in this series. Further, cytotoxicity of the potent conjugates of the series (7c, and 9a-c) was evaluated on human foreskin fibroblast (HFF) cells by using MTT assay. Finally, these studies suggest that compounds 7c and 9a may serve as promising lead scaffolds for further generation of new as anti-TB agents. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.028