N-[1-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-(tritylsulfanyl)ethyl]-N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amine | 329015-76-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[1-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-(tritylsulfanyl)ethyl]-N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amine
• 英文别名: N-[1-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-tritylsulfanylethyl]-4-(4-nitrophenyl)-1,3-thiazol-2-amine
• CAS: 329015-76-1
• 化学式: C₃₃H₂₈N₄O₄S₂
• 分子量: 608.742
• InChiKey: LJERJMIIOLKVFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.58
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  98.88
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-[1-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-(tritylsulfanyl)ethyl]-N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amine 在 三乙基硅烷 、 氟化铵 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-Bromo-6-{(S)-2-(5,6-dihydro-[1,4,2]dioxazin-3-yl)-2-[4-(4-nitro-phenyl)-thiazol-2-ylamino]-ethylsulfanylmethyl}-5-hydroxy-3-methoxy-benzoic acid methyl ester
  参考文献：
  名称：

  seco-Cyclothialidines:  New Concise Synthesis, Inhibitory Activity toward Bacterial and Human DNA Topoisomerases, and Antibacterial Properties

  摘要：

  seco-Cyclothialidines are a promising class of bacterial DNA gyrase B subunit inhibitors. A new seco-cyclothialidine derivative containing a dioxazine moiety, BAY 50-7952, was synthesized through a new concise pathway. One key step of the synthesis is the straightforward formation of the 2-aminothiazole derivative of S-tritylcysteine In biological tests, BAY 50-7952 and other known seco-cyclothialidines exhibited high and selective activity toward bacterial DNA gyrase and toward Gram-positive bacteria. The dioxazine moiety and other similar groups were found to be important for the ability of the seco-cyclothialidines to penetrate bacterial membranes. The opposite enantiomer ((S)-form) of BAY 50-7952 was also synthesized, and neither significant target activity nor in vitro antibacterial activity were found, suggesting a highly selective fit of the (R)-form. Despite promising in vitro activity, only poor activity was found in the murine infection model.

  DOI：

  10.1021/jm0010623
• 作为产物：
  描述：

  4-硝基苯甲酰甲基硫氰酸酯 在 伯吉斯试剂 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 N-[1-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-(tritylsulfanyl)ethyl]-N-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amine
  参考文献：
  名称：

  seco-Cyclothialidines:  New Concise Synthesis, Inhibitory Activity toward Bacterial and Human DNA Topoisomerases, and Antibacterial Properties

  摘要：

  seco-Cyclothialidines are a promising class of bacterial DNA gyrase B subunit inhibitors. A new seco-cyclothialidine derivative containing a dioxazine moiety, BAY 50-7952, was synthesized through a new concise pathway. One key step of the synthesis is the straightforward formation of the 2-aminothiazole derivative of S-tritylcysteine In biological tests, BAY 50-7952 and other known seco-cyclothialidines exhibited high and selective activity toward bacterial DNA gyrase and toward Gram-positive bacteria. The dioxazine moiety and other similar groups were found to be important for the ability of the seco-cyclothialidines to penetrate bacterial membranes. The opposite enantiomer ((S)-form) of BAY 50-7952 was also synthesized, and neither significant target activity nor in vitro antibacterial activity were found, suggesting a highly selective fit of the (R)-form. Despite promising in vitro activity, only poor activity was found in the murine infection model.

  DOI：

  10.1021/jm0010623