4-Chloro-2-(methylsulfonyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole-5-carboxaldehyde | 1093265-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-Chloro-2-(methylsulfonyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole-5-carboxaldehyde
• 英文别名: 5-chloro-2-methylsulfonyl-3-(2-trimethylsilylethoxymethyl)imidazole-4-carbaldehyde
• CAS: 1093265-18-9
• 化学式: C₁₁H₁₉ClN₂O₄SSi
• 分子量: 338.887
• InChiKey: LKZUUABYSLKLMA-UHFFFAOYSA-N

物化性质

• 沸点：
  455.4±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  78.26
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-Chloro-2-(methylsulfonyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole-5-carboxaldehyde 在 sodium chlorite 、 sodium azide 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 叔丁醇 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-azido-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid
  参考文献：
  名称：

  Rational Design of Potent Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase

  摘要：

  A new series of non-nucleoside reverse transcriptase inhibitors based on an imidazole-amide biarylether scaffold has been identified and shown to possess potent antiviral activity against HIV-1, including the NNRTI-resistant Y188L mutated virus. X-ray crystallography of inhibitors bound to reverse transcriptase, including a structure of the Y188L RT protein, was used extensively to help identify and optimize the key hydrogen-bonding motif. This led directly to the design of compound 43 that exhibits remarkable antiviral activity (EC50 < 1 nM) against a wide range of NNRTI-resistant viruses and a favorable pharmacokinetic profile across multiple species.

  DOI：

  10.1021/jm301294g
• 作为产物：
  描述：

  2-bromo-4,5-dichloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.16h， 生成 4-Chloro-2-(methylsulfonyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole-5-carboxaldehyde
  参考文献：
  名称：

  Rational Design of Potent Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase

  摘要：

  A new series of non-nucleoside reverse transcriptase inhibitors based on an imidazole-amide biarylether scaffold has been identified and shown to possess potent antiviral activity against HIV-1, including the NNRTI-resistant Y188L mutated virus. X-ray crystallography of inhibitors bound to reverse transcriptase, including a structure of the Y188L RT protein, was used extensively to help identify and optimize the key hydrogen-bonding motif. This led directly to the design of compound 43 that exhibits remarkable antiviral activity (EC50 < 1 nM) against a wide range of NNRTI-resistant viruses and a favorable pharmacokinetic profile across multiple species.

  DOI：

  10.1021/jm301294g