1-acetyl-2-chloromethyl-1H-benzoimidazole | 19809-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-acetyl-2-chloromethyl-1H-benzoimidazole
• 英文别名: 1-Acetyl-2-(chloromethyl)-1H-benzimidazole；1-[2-(Chloromethyl)-1h-benzimidazol-1-yl]ethanone；1-[2-(chloromethyl)benzimidazol-1-yl]ethanone
• CAS: 19809-02-0
• 化学式: C₁₀H₉ClN₂O
• 分子量: 208.647
• InChiKey: XOAVRYNXKLYQMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  359.3±44.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氯甲基苯并咪唑 在 4-二甲氨基吡啶 作用下， 以 Ac₂O 为溶剂， 以57%的产率得到1-acetyl-2-chloromethyl-1H-benzoimidazole
  参考文献：
  名称：

  Benzimidazole compounds and antiviral uses thereof

  摘要：

  本发明涉及具有有用抗病毒活性的新型苯并咪唑化合物。更具体地说，该发明涵盖了抑制与膜融合相关事件（如病毒传播）、减少病毒载量或以其他方式治疗病毒感染的苯并咪唑化合物。该发明还包括将苯并咪唑化合物用作抑制与膜融合相关事件（如病毒传播）的抑制剂。在另一个实施例中，该发明涵盖了制备苯并咪唑化合物的方法、使用苯并咪唑化合物的方法以及包含苯并咪唑化合物的组合物。最后，该发明提供了利用本发明的新型苯并咪唑化合物治疗、预防或缓解与呼吸道感染相关症状，尤其是由呼吸道合胞病毒引起的方法。

  公开号：

  US20030119754A1

文献信息

• Synthesis and Antifungal Activity of 2-Chloromethyl-1<i>H</i>-benzimidazole Derivatives against Phytopathogenic Fungi in Vitro
  作者：Yu-Bin Bai、An-Ling Zhang、Jiang-Jiang Tang、Jin-Ming Gao

  DOI：10.1021/jf3053934

  日期：2013.3.20

  A series of 35 benzimidazole derivatives were synthesized from 2-chloromethyl-1H-benzimidazole in good yields. Their structures were characterized by H-1 and C-13 NMR and HRESIMS. Antifungal activities of all of the synthesized compounds were evaluated against five phytopathogens fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani) using the mycelium growth rate method. Compound 4m displayed strong growth inhibition of C. gloeosporioides, A. solani, and F. solani with IC50 of 20.76, 27.58, and 18.60 mu g/mL, respectively. Selective inhibition of B. cinerea instead of the other fungal pathogenes was observed with 7f (IC50 of 13.36 mu g/mL), comparable to that of positive control, a commercial agricultural fungicide hymexazol (IC50 of 8.92 mu g/mL). Compound 51) exhibited remarkable antifungal properties against Cytospora sp., C. gloeosporioides, B. cinerea, and F. solani with IC50 values of 30.97, 11.38, 57.71, and 40.15 mu g/mL, respectively; among the target fungi, 5b was the most active compound and superior to the reference against C. gloeosporioides alone. Structure-activity relationship (SAR) data of these compounds are as follows: (1) introduction of the, chlorine atom on para-position in the benzene ring help to increase activity (4f vs 4c; 7f vs 7n), (2) the sulfonyl group is critical for the inhibition of C. gloeosporioides (51) and 5c vs 5a), and (3) the unsubstituted benzene ring improve activity (4m vs 4n, 4e and 4a). Thus, compounds 5b, 4m, and 7f emerged as a new leading structure for the development of new fungicides.
• US7030150B2
  申请人：——

  公开号：US7030150B2

  公开（公告）日：2006-04-18
• [EN] BENZIMIDAZOLE COMPOUNDS AND ANTIVIRAL USES THEREOF<br/>[FR] COMPOSES DE BENZIMIDAZOLE ET UTILISATIONS ANTIVIRALES
  申请人：TRIMERIS INC

  公开号：WO2002092575A1

  公开（公告）日：2002-11-21

  The present invention relates to novel benzimidazole compounds that have useful antiviral activity. More specifically, the invention encompasses benzimidazole compounds that inhibit membrane fusion associated events such as viral transmission, reduce viral load or otherwise treat viral infections. The invention also encompasses the use of benzimidazole compounds as inhibitors of membrane fusion associated events, such as transmission. In another embodiment, the invention encompasses processes for making benzimidazole compounds, methods of using the benzimidazole compounds and compositions comprizing the benzimidazole compounds. Finally, the invention provides methods for treating, preventing or ameliorating symptoms associated with respiratory infection, particularly that caused by Respiratory Syncytial Virus utilizing the novel benzimidazole compounds of the invention.
• Benzimidazole compounds and antiviral uses thereof
  申请人：——

  公开号：US20030119754A1

  公开（公告）日：2003-06-26

  The present invention relates to novel benzimidazole compounds that have useful antiviral activity. More specifically, the invention encompasses benzimidazole compounds that inhibit membrane fusion associated events such as viral transmission, reduce viral load or otherwise treat viral infections. The invention also encompasses the use of benzimidazole compounds as inhibitors of membrane fusion associated events, such as viral transmission. In another embodiment, the invention encompasses processes for making benzimidazole compounds, methods of using the benzimidazole compounds and compositions comprising the benzimidazole compounds. Finally, the invention provides methods for treating, preventing or ameliorating symptoms associated with respiratory infection, particularly that caused by Respiratory Syncytial Virus utilizing the novel benzimidazole compounds of the invention.

  本发明涉及具有有用抗病毒活性的新型苯并咪唑化合物。更具体地说，该发明涵盖了抑制与膜融合相关事件（如病毒传播）、减少病毒载量或以其他方式治疗病毒感染的苯并咪唑化合物。该发明还包括将苯并咪唑化合物用作抑制与膜融合相关事件（如病毒传播）的抑制剂。在另一个实施例中，该发明涵盖了制备苯并咪唑化合物的方法、使用苯并咪唑化合物的方法以及包含苯并咪唑化合物的组合物。最后，该发明提供了利用本发明的新型苯并咪唑化合物治疗、预防或缓解与呼吸道感染相关症状，尤其是由呼吸道合胞病毒引起的方法。