2-chloromethyl-1-methanesulfonyl-1H-benzoimidazole | 43215-12-9

• 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: 2-chloromethyl-1-methanesulfonyl-1H-benzoimidazole
• 英文别名: 2(Chloromethyl)-1-(methylsulfonyl)benzimidazol；2-(Chloromethyl)-1-(methylsulfonyl)-1h-benzimidazole；2-(chloromethyl)-1-methylsulfonylbenzimidazole
• CAS: 43215-12-9
• 化学式: C₉H₉ClN₂O₂S
• 分子量: 244.702
• InChiKey: XHMADHOBJDAENF-UHFFFAOYSA-N

物化性质

• 沸点：
  423.3±47.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-1-methanesulfonyl-1H-benzoimidazole 在 sodium hydride 、 potassium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 2-(benzotriazol-1-ylmethyl)benzimidazole
  参考文献：
  名称：

  Fundamental structure–Activity relationships associated with a new structural class of respiratory syncytial virus inhibitor

  摘要：

  Structure-activity relationships surrounding the dialkylamino side chain of a series of benzotriazole-derived inhibitors of respiratory syncytial virus fusion based on the screening lead 1a were examined. The results indicate that the topology of the side chain is important but the terminus element offers considerable latitude to modulate physical properties. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00383-4
• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 20.0h， 生成 2-chloromethyl-1-methanesulfonyl-1H-benzoimidazole
  参考文献：
  名称：

  Synthesis and Antifungal Activity of 2-Chloromethyl-1H-benzimidazole Derivatives against Phytopathogenic Fungi in Vitro

  摘要：

  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.

  DOI：

  10.1021/jf3053934

文献信息

• Substituted benzimidazole antiviral agents
  申请人：——

  公开号：US20030139450A1

  公开（公告）日：2003-07-24

  The present invention concerns antiviral compounds, their compositions, and use in the treatment of viral infections. More particularly, the invention provides benzimidazole derivatives for the treatment of respiratory syncytial virus infection.

  本发明涉及抗病毒化合物、它们的组合物以及在治疗病毒感染中的应用。更具体地说，本发明提供苯并咪唑衍生物用于治疗呼吸道合胞病毒感染。
• Synthesis of benzimidazole fused poly-heterocycles <i>via</i> oxidant free Cu-catalyzed dehydrogenative C–N coupling and photophysical studies
  作者：Sakshi Singh、Shantanu Pal

  DOI：10.1039/d3cc03931e

  日期：——

  A unique example of Cu-catalysed synthesis of benzimidazole fused poly-heterocycles via intramolecular C–N coupling reaction has been reported.

  报告了一个通过分子内 C-N 偶联反应铜催化合成苯并咪唑融合多杂环的独特实例。
• US6774134B2
  申请人：——

  公开号：US6774134B2

  公开（公告）日：2004-08-10
• US6908936B2
  申请人：——

  公开号：US6908936B2

  公开（公告）日：2005-06-21
• US7030140B2
  申请人：——

  公开号：US7030140B2

  公开（公告）日：2006-04-18