4,6-dichloro-2-trichloromethylbenzimidazole | 148729-69-5

• 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: 4,6-dichloro-2-trichloromethylbenzimidazole
• 英文别名: 4,6-dichloro-2-trichloromethyl-1H-benzoimidazole；4,6-dichloro-2-(trichloromethyl)-1H-benzimidazole
• CAS: 148729-69-5
• 化学式: C₈H₃Cl₅N₂
• 分子量: 304.39
• InChiKey: NXCKYOGSYXCXGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-2-trichloromethylbenzimidazole 在 sodium hydroxide 作用下， 以95%的产率得到4,6-dichlorobenzimidazole-2-carboxylic acid
  参考文献：
  名称：

  Novel benzimidazoles as ligands for the strychnine-insensitive N-methyl-d-aspartate-linked glycine receptor

  摘要：

  Two new benzimidazole derivatives were synthesized and evaluated for their ability to inhibit the binding at the strychnine-insensitive N-methyl-D-aspartate(NMDA)-linked glycine receptor. The most potent one, the 4,6-dichlorobenzimidazole-2-carboxylic acid 6, was found to have submicromolar affinity for this receptor. The result of its functional test suggests that it acts as an antagonist of the NMDA receptor complex. Thus, this class of benzimidazole derivatives seems to constitute a group of potential antagonists for the strychnine-insensitive glycine receptor.

  DOI：

  10.1016/0223-5234(93)90080-x
• 作为产物：
  描述：

  2,4-二氯-6-硝基苯胺 在 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4,6-dichloro-2-trichloromethylbenzimidazole
  参考文献：
  名称：

  Novel benzimidazoles as ligands for the strychnine-insensitive N-methyl-d-aspartate-linked glycine receptor

  摘要：

  Two new benzimidazole derivatives were synthesized and evaluated for their ability to inhibit the binding at the strychnine-insensitive N-methyl-D-aspartate(NMDA)-linked glycine receptor. The most potent one, the 4,6-dichlorobenzimidazole-2-carboxylic acid 6, was found to have submicromolar affinity for this receptor. The result of its functional test suggests that it acts as an antagonist of the NMDA receptor complex. Thus, this class of benzimidazole derivatives seems to constitute a group of potential antagonists for the strychnine-insensitive glycine receptor.

  DOI：

  10.1016/0223-5234(93)90080-x

文献信息

• Preparation and Biological Evaluation of Indole, Benzimidazole, and Thienopyrrole Piperazine Carboxamides:  Potent Human Histamine H₄ Antagonists
  作者：Jennifer D. Venable、Hui Cai、Wenying Chai、Curt A. Dvorak、Cheryl A. Grice、Jill A. Jablonowski、Chandra R. Shah、Annette K. Kwok、Kiev S. Ly、Barbara Pio、Jianmei Wei、Pragnya J. Desai、Wen Jiang、Steven Nguyen、Ping Ling、Sandy J. Wilson、Paul J. Dunford、Robin L. Thurmond、Timothy W. Lovenberg、Lars Karlsson、Nicholas I. Carruthers、James P. Edwards

  DOI：10.1021/jm0502081

  日期：2005.12.1

  lipophilic groups in the 4 and 5-positions led to increased activity in a [(3)H]histamine radiolabeled ligand competitive binding assay. In vitro metabolism and initial pharmacokinetic studies were performed on selected compounds leading to the identification of indole 8 and benzimidazole 40 as potent H(4) antagonists with the potential for further development. In addition, both 8 and 40 demonstrated

  从吲哚基-2-基-（4-甲基-哌嗪-1-基）-亚甲基衍生的三个系列的H（4）受体配体已合成，并评估了它们在H（4）上的活性构架关系竞争性结合和功能测定中的受体。在所有情况下，在[（3）H]组胺放射性标记的配体竞争性结合试验中，在4和5位上的亲脂性小基团的取代导致活性增加。对选定的化合物进行了体外代谢和初步药代动力学研究，从而导致将吲哚8和苯并咪唑40鉴定为潜在的H（4）拮抗剂，具有进一步开发的潜力。此外，8和40均在体外肥大细胞和嗜酸性粒细胞趋化性测定中显示出功效。
• Octahydropyrrolo[3,4-C]pyrrole derivatives
  申请人：Lane Alice Louise Charlotte

  公开号：US20060111416A1

  公开（公告）日：2006-05-25

  The present invention relates to octahydropyrrolo[3,4-c]pyrrole derivatives of formula (I): and to processes for the preparation thereof, compositions containing the same and the uses thereof.

  本发明涉及式(I)的八氢吡咯并[3,4-c]吡咯衍生物，以及其制备方法、含有该衍生物的组合物和用途。
• Octahydropyrrolo[3,4-c]pyrrole derivatives
  申请人：Pfizer Limited

  公开号：EP1671972A1

  公开（公告）日：2006-06-21

  The present invention relates to octahydropyrrolo[3,4-c]pyrrole derivatives of formula (I): and to processes for the preparation thereof, compositions containing the same and the uses thereof.

  本发明涉及式（I）的八氢吡咯并[3,4-c]吡咯衍生物： 及其制备工艺、含有这些衍生物的组合物及其用途。
• Inhibitors of cysteine proteases and methods of use thereof
  申请人：Pardes Biosciences, Inc.

  公开号：US11174231B1

  公开（公告）日：2021-11-16

  The disclosure provides compounds with warheads and their use in treating medical diseases or disorders, such as viral infections. Pharmaceutical compositions and methods of making various compounds with warheads are provided. The compounds are contemplated to inhibit proteases, such as the 3C, CL- or 3CL-like protease.

  本公开提供了带有弹头的化合物及其在治疗医学疾病或失调（如病毒感染）中的用途。提供了药物组合物和制造各种带弹头化合物的方法。这些化合物可用于抑制蛋白酶，如 3C、CL 或 3CL 样蛋白酶。
• [EN] INHIBITORS OF CYSTEINE PROTEASES AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE CYSTÉINE PROTÉASES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：PARDES BIOSCIENCES INC

  公开号：WO2021252644A1

  公开（公告）日：2021-12-16

  The disclosure provides compounds of formula II with warheads and their use in treating medical diseases or disorders, such as viral infections. Pharmaceutical compositions and methods of making various compounds with warheads are provided. The compounds are contemplated to inhibit proteases, such as the 3C, CL- or 3CL-like protease. Formula II