2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-methoxy-6-{(R)-2-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-[4-(4-nitro-phenyl)-thiazol-2-ylamino]-ethylsulfanylmethyl}-benzoic acid methyl ester | 329015-87-4

• 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: 2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-methoxy-6-{(R)-2-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-[4-(4-nitro-phenyl)-thiazol-2-ylamino]-ethylsulfanylmethyl}-benzoic acid methyl ester
• 英文别名: methyl 2-bromo-5-[2,3-dimethylbutan-2-yl(dimethyl)silyl]oxy-3-methoxy-6-[[(2R)-2-(3-methyl-1,2,4-oxadiazol-5-yl)-2-[[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino]ethyl]sulfanylmethyl]benzoate
• CAS: 329015-87-4
• 化学式: C₃₂H₄₀BrN₅O₇S₂Si
• 分子量: 778.82
• InChiKey: IFQZZYOXNZSWNY-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.07
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  208
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-methoxy-6-{(R)-2-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-[4-(4-nitro-phenyl)-thiazol-2-ylamino]-ethylsulfanylmethyl}-benzoic acid methyl ester 在 氟化铵 作用下， 以 甲醇 为溶剂， 生成 (2(R)-(4-(4-nitrophenyl) thiazol-2-yl)amino-2-(3-methyl-1,2,4-oxadiazol-5-yl)ethylthio)methyl-3-hydroxy-5-methoxy-6-bromobenzoic 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 三乙基硅烷 、 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 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 43.0h， 生成 2-Bromo-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-methoxy-6-{(R)-2-(3-methyl-[1,2,4]oxadiazol-5-yl)-2-[4-(4-nitro-phenyl)-thiazol-2-ylamino]-ethylsulfanylmethyl}-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