1-Benzyl-5-(3-chloro-phenyl)-1,3-dihydro-benzoimidazol-2-one | 396726-00-4

• 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-Benzyl-5-(3-chloro-phenyl)-1,3-dihydro-benzoimidazol-2-one
• 英文别名: 3-benzyl-6-(3-chlorophenyl)-1H-benzimidazol-2-one
• CAS: 396726-00-4
• 化学式: C₂₀H₁₅ClN₂O
• 分子量: 334.805
• InChiKey: JTJWERWUFWISDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  1-Benzyl-5-(3-chloro-phenyl)-1,3-dihydro-benzoimidazol-2-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以60%的产率得到1-Benzyl-5-(3-chloro-phenyl)-1,3-dihydro-benzoimidazole-2-thione
  参考文献：
  名称：

  Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones

  摘要：

  Novel 6-aryl benzimidazolones and benzothiazolones were prepared and examined as bioisosteres of the recently reported 6-aryl dihydroquinolines (1) for progesterone receptor (PR) antagonist activities. PR antagonist activities increased when compounds 9c-f possessed a more lipophilic group at position-1 and pendent aryl moiety para to NH moiety. Furthermore, conversion of carbonyl moiety of 9e,f to the thio-carbonyl led to benzoimidazolethiones 15a,b with significantly improved potency and binding affinity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00554-6
• 作为产物：
  描述：

  佰能-BB 在 四(三苯基膦)钯 、 potassium carbonate 、 异丙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 生成 1-Benzyl-5-(3-chloro-phenyl)-1,3-dihydro-benzoimidazol-2-one
  参考文献：
  名称：

  Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones

  摘要：

  Novel 6-aryl benzimidazolones and benzothiazolones were prepared and examined as bioisosteres of the recently reported 6-aryl dihydroquinolines (1) for progesterone receptor (PR) antagonist activities. PR antagonist activities increased when compounds 9c-f possessed a more lipophilic group at position-1 and pendent aryl moiety para to NH moiety. Furthermore, conversion of carbonyl moiety of 9e,f to the thio-carbonyl led to benzoimidazolethiones 15a,b with significantly improved potency and binding affinity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00554-6

文献信息

• BENZIMIDAZOLONES AND ANALOGUES AND THEIR USE AS PROGESTERONE RECEPTOR LIGANDS
  申请人：American Home Products Corporation

  公开号：EP1173423A1

  公开（公告）日：2002-01-23
• [EN] BENZIMIDAZOLONES AND ANALOGUES AND THEIR USE AS PROGESTERONE RECEPTOR LIGANDS<br/>[FR] BENZIMIDAZOLONES ET ANALOGUES ET LEUR UTILISATION COMME LIGANDS DU RECEPTEUR DE PROGESTERONE
  申请人：AMERICAN HOME PROD

  公开号：WO2000066564A1

  公开（公告）日：2000-11-09

  The present invention provides compounds and pharmaceutical formulations useful as progesterone receptor agonists and antagonists and having general formula (a): wherein A is O, S, or NR4; B is a bond between A and C=Q, or the moiety CR?5R6; R4, R5, R6¿ are independently selected from H or optionally substituted C¿1? to C6 alkyl, C2 to C6 alkenyl, C2 to C6 alkynyl, C3 to C8 cycloalkyl, substituted C3 to C8 cycloalkyl, aryl, or heteorcyclic groups, or cyclic alkyl constructed by fusing R?4 and R5¿ to from a 5 to 7 membered ring; R1 is selected from H, OH, NH¿2?, C1 to C6 alkyl, substituted C1 to C6 alkyl, C3 to C6 alkenyl, substituded C1 to C6 alkenyl, alkynyl, substituted alkynyl, -COH, or optionally substituted -CO(C1 to C3 alkyl), -CO(aryl), -CO(C1 to C3 alkoxy), or -CO(C1 toC3 aminoalkyl) groups; R?2¿ is selected from H, halogen, CN, NO¿2?, or optionally substituted C1 to C6 alkyl, C1 to C6 alkoxy, or C1 to C6 aminoalkyl groups; R?3¿ is selected from a trisubstituted benzene ring; or a 5- or 6- membered heteroaromatic ring containing 1 or 2 substituents; Q is O, S, NR?8, or CR9R10¿; or a pharmaceutically acceptable salt thereof. The invention also includes methods of contraception and methods of treating or preventing maladies associated with the progesterone receptor.
• Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones
  作者：Puwen Zhang、Eugene A. Terefenko、Jay Wrobel、Zhiming Zhang、Yuan Zhu、Jeffrey Cohen、Keith B. Marschke、Dale Mais

  DOI：10.1016/s0960-894x(01)00554-6

  日期：2001.10

  Novel 6-aryl benzimidazolones and benzothiazolones were prepared and examined as bioisosteres of the recently reported 6-aryl dihydroquinolines (1) for progesterone receptor (PR) antagonist activities. PR antagonist activities increased when compounds 9c-f possessed a more lipophilic group at position-1 and pendent aryl moiety para to NH moiety. Furthermore, conversion of carbonyl moiety of 9e,f to the thio-carbonyl led to benzoimidazolethiones 15a,b with significantly improved potency and binding affinity. (C) 2001 Elsevier Science Ltd. All rights reserved.