methyl 2-bromo-6-{[(2-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-{[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino}ethyl)sulfanyl]methyl}-5-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-3-methoxybenzoate | 329015-81-8

• 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: methyl 2-bromo-6-{[(2-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-{[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino}ethyl)sulfanyl]methyl}-5-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-3-methoxybenzoate
• 英文别名: methyl 2-bromo-6-[[2-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-[[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino]ethyl]sulfanylmethyl]-5-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3-methoxybenzoate
• CAS: 329015-81-8
• 化学式: C₃₂H₄₁BrN₄O₈S₂Si
• 分子量: 781.821
• InChiKey: LDCQALLIHOTULU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.37
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  143.64
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-6-{[(2-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-{[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino}ethyl)sulfanyl]methyl}-5-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-3-methoxybenzoate 在 氟化铵 作用下， 以 甲醇 为溶剂， 生成 2-Bromo-6-{(R)-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 、 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：

  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 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 methyl 2-bromo-6-{[(2-(5,6-dihydro-1,4,2-dioxazin-3-yl)-2-{[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino}ethyl)sulfanyl]methyl}-5-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-3-methoxybenzoate
  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