(S)-(+)-N-[4-(4-nitro-phenyl)-thiazol-2-yl]-S-(triphenylmethyl)-cysteine methyl ester | 287935-20-0

• 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: (S)-(+)-N-[4-(4-nitro-phenyl)-thiazol-2-yl]-S-(triphenylmethyl)-cysteine methyl ester
• 英文别名: N-[4-(4-nitrophenyl)thiazol-2-yl]-S-trityl-L-cysteine methyl ester；methyl (2R)-2-[[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino]-3-tritylsulfanylpropanoate
• CAS: 287935-20-0
• 化学式: C₃₂H₂₇N₃O₄S₂
• 分子量: 581.716
• InChiKey: LMDIDCWFNBUZCC-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-(+)-N-[4-(4-nitro-phenyl)-thiazol-2-yl]-S-(triphenylmethyl)-cysteine methyl ester 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-5-hydroxy-3-methoxy-6-{(R)-2-methoxycarbonyl-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
• 作为产物：
  描述：

  S-三苯甲基-L-半胱氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 (S)-(+)-N-[4-(4-nitro-phenyl)-thiazol-2-yl]-S-(triphenylmethyl)-cysteine 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

文献信息

• Facile Access to N-Thiazolyl α-Amino Acids from α-Bromo Ketones and α-Amino Acids
  作者：Joachim Rudolph

  DOI：10.1016/s0040-4020(00)00190-3

  日期：2000.5

  procedure using readily available α-bromo ketones and amines. This method is compatible with a wide range of functional groups and offers a facile and efficient access to the class of N-thiazolyl α-amino acid derivatives.

  使用容易获得的α-溴代酮和胺，通过一锅法合成N-取代的2-氨基噻唑。该方法与广泛的官能团相容，并且提供了对N-噻唑基α-氨基酸衍生物类别的便捷访问。
• <i>seco</i>-Cyclothialidines:  New Concise Synthesis, Inhibitory Activity toward Bacterial and Human DNA Topoisomerases, and Antibacterial Properties
  作者：Joachim Rudolph、Heidi Theis、Roman Hanke、Rainer Endermann、Lars Johannsen、Frank-Ulrich Geschke

  DOI：10.1021/jm0010623

  日期：2001.2.1

  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.