2-methyl-4-chloro-5-(hydroxymethyl)-imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-4-chloro-5-(hydroxymethyl)-imidazole
• 英文别名: (4-chloro-2-methyl-1H-imidazol-5-yl)methanol；4-Chloro-2-methyl-1H-imidazole-5-methanol；2-methyl-4-chloro-5-(hydroxymethyl) imidazole；[4-chloro-2-methyl-1H-imidazol-5-yl]methanol
• 化学式: C₅H₇ClN₂O
• 分子量: 146.576
• InChiKey: OTWQXOIKSKNJKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-4-chloro-5-(hydroxymethyl)-imidazole 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 4-chloro-2-methyl-1H-imidazole-5-carbaldehyde
  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：

  N-氯代丁二酰亚胺 以 1,4-二氧六环 、 乙二醇甲醚 为溶剂， 生成 2-methyl-4-chloro-5-(hydroxymethyl)-imidazole
  参考文献：
  名称：

  Benzofuran derivatives

  摘要：

  该发明提供了一般式(I)的化合物及其生理上可接受的盐、溶剂合物或非毒性代谢易降解酯，其中R.sup.1代表卤素原子；Ar代表该群；R.sup.3代表C-连接的四唑基团；R.sup.4和R.sup.5，可能相同也可能不同，各自独立地代表氢原子或卤素原子或C.sub.1-6烷基团；Het代表N-连接的咪唑基团，可选择地在2-位置上取代。这些化合物可用于治疗或预防高血压和与认知障碍相关的疾病。

  公开号：

  US05374646A1

文献信息

• Process for synthesizing 4-halo-5-(hydroxymethyl) imidazole compounds
  申请人：Shikoku Chemicals Corporation

  公开号：US05514811A1

  公开（公告）日：1996-05-07

  A process for preparing, on an industrial scale, 4-halo-5-(hydroxymethyl) imidazole compounds that are useful as intermediates for medicines. A 4-chloro-5-(hydroxymethyl) imidazole compound, a 4-bromo-5-(hydroxymethyl) imidazole compound or a like compound is synthesized by reacting a 4,5-bis(hydroxymethyl) imidazole compound with a halogenating agent such as an N-chlorosuccinimide, an N-bromosuccinimide, a chlorinated isocyanuric acid compound or the like compound.

  一种用于在工业规模下制备有用于药物中间体的4-卤代-5-(羟甲基)咪唑化合物的方法。通过将4,5-双(羟甲基)咪唑化合物与卤化剂（如N-氯琥珀酰亚胺、N-溴琥珀酰亚胺、氯化异氰尿酸化合物或类似化合物）反应合成4-氯-5-(羟甲基)咪唑化合物、4-溴-5-(羟甲基)咪唑化合物或类似化合物。
• 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。
• WO2008/154271
  申请人：——

  公开号：——

  公开（公告）日：——
• Process for synthesizing 4-halo-5(hydroxymethyl) imidazole compounds and certain novel 4-halo-5(hydroxymethyl) imidazole compounds
  申请人：SHIKOKU CHEMICALS CORPORATION

  公开号：EP0611758B1

  公开（公告）日：1996-10-16