4,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole | 1093266-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole
• 英文别名: tert-butyl-[[4,5-dichloro-1-(2-trimethylsilylethoxymethyl)imidazol-2-yl]methoxy]-dimethylsilane
• CAS: 1093266-40-0
• 化学式: C₁₆H₃₂Cl₂N₂O₂Si₂
• 分子量: 411.519
• InChiKey: UPWYVSSIQHZQOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole 在 sodium chlorite 、 正丁基锂 、 sodium dihydrogenphosphate dihydrate 、 2-甲基-2-丁烯 、 叔丁醇 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 1.17h， 生成 2-(((tert-butyldimethylsilyl)oxy)methyl)-4-chloro-1-((2-(trimethylsilyl)ethoxy)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 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 4,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole
  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

文献信息

• CHEMICAL COMPOUNDS
  申请人：Chong PEK Yoke

  公开号：US20100216746A1

  公开（公告）日：2010-08-26

  The present invention relates to compounds that are a non-nucleoside reverse transcriptase inhibitors, and to processes for the preparation and use of the same. Specifically, the present invention includes methods of using such compounds in the treatment of human immunodeficiency virus infection.

  本发明涉及一种非核苷类逆转录酶抑制剂，以及制备和使用该类化合物的方法。具体而言，本发明包括使用这些化合物治疗人类免疫缺陷病毒感染的方法。
• Chemical compounds
  申请人：GlaxoSmithKline LLC

  公开号：US08304419B2

  公开（公告）日：2012-11-06

  The present invention relates to compounds that are a non-nucleoside reverse transcriptase inhibitors, and to processes for the preparation and use of the same. Specifically, the present invention includes methods of using such compounds in the treatment of human immunodeficiency virus infection.

  本发明涉及一种非核苷类逆转录酶抑制剂化合物，以及制备和使用该化合物的方法。具体而言，本发明涉及使用这些化合物治疗人类免疫缺陷病毒感染的方法。