[3-(3,5-Difluoro-phenyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-acetic acid | 767305-41-9

• 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: [3-(3,5-Difluoro-phenyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-acetic acid
• CAS: 767305-41-9
• 化学式: C₁₅H₁₀F₂N₂O₃
• 分子量: 304.253
• InChiKey: BMWGZLITTGABCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.23
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-5'-amino-3-methyl-spiro[imidazolidine-4,2'-indane]-2,5-dione 、 [3-(3,5-Difluoro-phenyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-acetic acid 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[3-(3,5-difluorophenyl)-2-oxobenzimidazol-1-yl]-N-[(2R)-1'-methyl-2',4'-dioxospiro[1,3-dihydroindene-2,5'-imidazolidine]-5-yl]acetamide
  参考文献：
  名称：

  Identification of novel, orally bioavailable spirohydantoin CGRP receptor antagonists

  摘要：

  A rapid analogue approach to identification of spirohydantoin-based CGRP antagonists provided novel, low molecular weight leads. Modification of these leads afforded a series of nanomolar benzimidazolinone-based CGRP receptor antagonists. The oral bioavailability of these antagonists was inversely correlated with polar surface area, suggesting that membrane permeability was a key limitation to absorption. Optimization provided compound 12, a potent CGRP receptor antagonist (K-i = 21 nM) with good oral bioavailability in three species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.045
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 [3-(3,5-Difluoro-phenyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-acetic acid
  参考文献：
  名称：

  Identification of novel, orally bioavailable spirohydantoin CGRP receptor antagonists

  摘要：

  A rapid analogue approach to identification of spirohydantoin-based CGRP antagonists provided novel, low molecular weight leads. Modification of these leads afforded a series of nanomolar benzimidazolinone-based CGRP receptor antagonists. The oral bioavailability of these antagonists was inversely correlated with polar surface area, suggesting that membrane permeability was a key limitation to absorption. Optimization provided compound 12, a potent CGRP receptor antagonist (K-i = 21 nM) with good oral bioavailability in three species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.045