3-(3-cyclobutyl-2-thioxo-2,3-dihydro-1H-benzimidazol-5-yl)-5-fluorobenzonitrile | 952050-51-0

• 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-cyclobutyl-2-thioxo-2,3-dihydro-1H-benzimidazol-5-yl)-5-fluorobenzonitrile
• 英文别名: 3-(3-cyclobutyl-2-sulfanylidene-1H-benzimidazol-5-yl)-5-fluorobenzonitrile
• CAS: 952050-51-0
• 化学式: C₁₈H₁₄FN₃S
• 分子量: 323.394
• InChiKey: CUPMKQRSISGSTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(3-cyclobutyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)-5-fluorobenzonitrile 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以33%的产率得到3-(3-cyclobutyl-2-thioxo-2,3-dihydro-1H-benzimidazol-5-yl)-5-fluorobenzonitrile
  参考文献：
  名称：

  5-(3-Cyclopentyl-2-thioxo-2,3-dihydro-1H-benzimidazol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile: A novel, highly potent, selective, and orally active non-steroidal progesterone receptor agonist

  摘要：

  We have recently discovered 5-(3-cyclopentyl-2-thioxo-2,3-dihydro- I H-benzimidazol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (14) as a potent, selective, and orally active non-steroidal progesterone receptor (PR) agonist. Compound 14 and its analog 13 possessed sub-nanomolar in vitro potency (EC50 0.1-0.5 nM) in the T47D alkaline phosphatase assay, similar to that of the steroidal PR agonist medroxyprogesterone acetate (MPA). In contrast to MPA, 14 was highly selective (> 500-fold) for the PR over both glucocorticoid and androgen receptors. In the rat uterine decidualization and complement component C3 models, 14 had oral ED50 values of 0.02 and 0.003 mg/kg, respectively, and was from 6- to 20-fold more potent than MPA. In the monkey ovulation inhibition model, compound 14 was also highly efficacious and potent with an oral ED100 of 0.03 mg/kg. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.011

文献信息

• 5-(3-Cyclopentyl-2-thioxo-2,3-dihydro-1H-benzimidazol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile: A novel, highly potent, selective, and orally active non-steroidal progesterone receptor agonist
  作者：Puwen Zhang、Eugene Terefenko、Jeffrey Kern、Andrew Fensome、Eugene Trybulski、Ray Unwalla、Jay Wrobel、Susan Lockhead、Yuan Zhu、Jeffrey Cohen、Margaret LaCava、Richard C. Winneker、Zhiming Zhang

  DOI：10.1016/j.bmc.2007.07.011

  日期：2007.10

  We have recently discovered 5-(3-cyclopentyl-2-thioxo-2,3-dihydro- I H-benzimidazol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (14) as a potent, selective, and orally active non-steroidal progesterone receptor (PR) agonist. Compound 14 and its analog 13 possessed sub-nanomolar in vitro potency (EC50 0.1-0.5 nM) in the T47D alkaline phosphatase assay, similar to that of the steroidal PR agonist medroxyprogesterone acetate (MPA). In contrast to MPA, 14 was highly selective (> 500-fold) for the PR over both glucocorticoid and androgen receptors. In the rat uterine decidualization and complement component C3 models, 14 had oral ED50 values of 0.02 and 0.003 mg/kg, respectively, and was from 6- to 20-fold more potent than MPA. In the monkey ovulation inhibition model, compound 14 was also highly efficacious and potent with an oral ED100 of 0.03 mg/kg. (c) 2007 Elsevier Ltd. All rights reserved.