5-Chloro-1,3-dihydro-1-(methylethenyl)-2H-benzimidazol-2-one | 40582-24-9

• 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: 5-Chloro-1,3-dihydro-1-(methylethenyl)-2H-benzimidazol-2-one
• 英文别名: 5-chloro-1-isopropenyl-1,3-dihydro-benzoimidazol-2-one；2H-Benzimidazol-2-one, 5-chloro-1,3-dihydro-1-(1-methylethenyl)-；6-chloro-3-prop-1-en-2-yl-1H-benzimidazol-2-one
• CAS: 40582-24-9
• 化学式: C₁₀H₉ClN₂O
• 分子量: 208.647
• InChiKey: OWJAPZDJSGKBNJ-UHFFFAOYSA-N

物化性质

• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Chloro-1,3-dihydro-1-(methylethenyl)-2H-benzimidazol-2-one 在 sodium hydroxide 、 硫酸 、 sodium ethanolate 作用下， 生成 (6-chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)acetic acid
  参考文献：
  名称：

  Benzimidazoles as NMDA Glycine-Site Antagonists: Study on the Structural Requirements in 2-Position of the Ligand

  摘要：

  A series of different substituted benzimidazole derivatives has been synthesized and evaluated for the ability to displace [3H]MDL-105,519 to rat cortical membranes. Two benzimidazole-2-carboxylic acids 9 b and 9 c, in this substitution pattern not yet described as glycine antagonists, showed IC50 values of 0.89 microM (9 b) and 38.0 microM (9 c). Replacement of the carboxylate function in 2-position by a sulfonic acid moiety appreciably increased solubility, but decreased the affinity giving evidence for the strong need of the carboxylate group within the ligand. Further structure-activity studies using benzimidazole-2-one derivatives with an acetic acid moiety adjacent to a ring nitrogen revealed new insights into the importance of amide functionalities within the heterocycle for the affinity of antagonist glycine-site ligands.

  DOI：

  10.1002/(sici)1521-4184(20005)333:5<123::aid-ardp123>3.0.co;2-5
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-氯-1,2-苯二胺 在 氢氧化钾 作用下， 以 乙醇 、 水 、 xylene 为溶剂， 反应 5.0h， 以34%的产率得到6-Chloro-1,3-dihydro-1-(methylethenyl)-2H-benzimidazol-2-one
  参考文献：
  名称：

  Gomez-Parra, Vicente; Jimenez, Mercedes; Sanchez, Felix, Liebigs Annalen der Chemie, 1989, p. 539 - 544

  摘要：

  DOI：

文献信息

• [EN] DERIVATIVE OF METHACRYLOYL-BENZIMIDAZOL-ONE (THIONE) AND USE THEREOF AS ANTI-MICROBIAL DRUG<br/>[FR] DÉRIVÉ DE MÉTHACRYLOYL-BENZIMIDAZOL-ONE (THIONE) ET SON UTILISATION EN TANT QUE MÉDICAMENT ANTIMICROBIEN
  申请人：UNIV NORTHWEST A&F

  公开号：WO2013059984A1

  公开（公告）日：2013-05-02

  本发明公开了一类新的甲基丙烯酰基苯并咪唑（硫）酮衍生物，该化合物的制备方法，以及该化合物作为抗菌药物的用途。该化合物具有如下通式（I）所示结构，式中R和Y具有如说明书所述的含义。
• Benzimidazoles as NMDA Glycine-Site Antagonists: Study on the Structural Requirements in 2-Position of the Ligand
  作者：Gerd Dannhardt、Beate K. Kohl

  DOI：10.1002/(sici)1521-4184(20005)333:5<123::aid-ardp123>3.0.co;2-5

  日期：2000.5

  A series of different substituted benzimidazole derivatives has been synthesized and evaluated for the ability to displace [3H]MDL-105,519 to rat cortical membranes. Two benzimidazole-2-carboxylic acids 9 b and 9 c, in this substitution pattern not yet described as glycine antagonists, showed IC50 values of 0.89 microM (9 b) and 38.0 microM (9 c). Replacement of the carboxylate function in 2-position by a sulfonic acid moiety appreciably increased solubility, but decreased the affinity giving evidence for the strong need of the carboxylate group within the ligand. Further structure-activity studies using benzimidazole-2-one derivatives with an acetic acid moiety adjacent to a ring nitrogen revealed new insights into the importance of amide functionalities within the heterocycle for the affinity of antagonist glycine-site ligands.
• Gomez-Parra, Vicente; Jimenez, Mercedes; Sanchez, Felix, Liebigs Annalen der Chemie, 1989, p. 539 - 544
  作者：Gomez-Parra, Vicente、Jimenez, Mercedes、Sanchez, Felix、Torres, Tomas

  DOI：——

  日期：——