5-Bromo-3-isopropyl-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester | 396725-93-2

• 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-Bromo-3-isopropyl-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester
• CAS: 396725-93-2
• 化学式: C₁₅H₁₉BrN₂O₃
• 分子量: 355.231
• InChiKey: STDNFIFZLNVQRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  53.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-Bromo-3-isopropyl-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester 在 四(三苯基膦)钯 、 potassium carbonate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 6-(3,4-Difluoro-phenyl)-1-isopropyl-1,3-dihydro-benzoimidazol-2-one
  参考文献：
  名称：

  SAR studies of 6-aryl-1,3-dihydrobenzimidazol-2-ones as progesterone receptor antagonists

  摘要：

  We have previously reported that the aryl substituted benzimidazolones, benzoxazinones, and oxindoles (e.g., 1-3) are progesterone receptor (PR) antagonists and have recently disclosed that the nature of 5- and 6-aryl moieties played a critical role in PR functional activity in the oxindole and benzoxazinone templates. For example, replacing the phenyl group of PR antagonists 2 and 3 with a 5'-cyanopyrrol-2'-yl moiety switched their functional activity to PR agonist activity (2a and 3a). These findings prompted us to examine if there is a similar effect of the 6-aryl moieties on the PR functional activity for the benzimidazolone template. Numerous analogs, such as 5, showed potent PR antagonist activity with about a 10-fold increase in potency as compared to those reported earlier in the same series. More interestingly, pyrrole-containing benzimidazolones 24-27 remained as PR antagonists in contrast to the PR agonist activity switch for oxindole and benzoxazinone scaffolds when a 5'-cyanopyrrol-2'-yl group was installed as a pendant aryl group. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.082
• 作为产物：
  描述：

  异丙醇 、 5-溴-2-氧代-2,3-二氢-1H-苯并[D]咪唑-1-羧酸叔丁酯 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 5-Bromo-3-isopropyl-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester
  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