1,5-二甲基-1,3-二氢-2H-苯并咪唑-2-硫酮 | 149530-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1,5-二甲基-1,3-二氢-2H-苯并咪唑-2-硫酮
• 中文别名: 1,5-二甲基-1H-苯并[D]咪唑-2(3H)-硫酮
• 英文名称: 5-methylbenzimidazoline-2-thione
• 英文别名: 1,5-dimethyl-1,3-dihydro-benzimidazole-2-thione；1,5-Dimethyl-1,3-dihydro-benzimidazol-2-thion；1,5-Dimethyl-1H-benzo[d]imidazole-2(3H)-thione；3,6-dimethyl-1H-benzimidazole-2-thione
• CAS: 149530-79-0
• 化学式: C₉H₁₀N₂S
• 分子量: 178.258
• InChiKey: NUQZVIXXDIASPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.4
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(bromoacetyl)-N-[2-(1H-pyrrol-1-yl)phenyl]-L-prolinamide 、 1,5-二甲基-1,3-二氢-2H-苯并咪唑-2-硫酮 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S)-1-[2-(1,5-dimethylbenzimidazol-2-yl)sulfanylacetyl]-N-(2-pyrrol-1-ylphenyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Proline bis-amides as potent dual orexin receptor antagonists

  摘要：

  A series of OX2R/OX1R dual orexin antagonists was prepared based on a proline bis-amide identified as a screening lead. Through a combination of classical and library synthesis, potency enhancing replacements for both amide portions were discovered. N-methylation of the benzimidazole moiety within the lead structure significantly reduced P-gp susceptibility while increasing potency, giving rise to good brain penetration. A compound from this series has demonstrated in vivo central activity when dosed peripherally in a pharmacodynamic model of orexin activity. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2008.01.001
• 作为产物：
  描述：

  4,N-dimethyl-2-nitroaniline 在 盐酸 、 tin 作用下， 生成 1,5-二甲基-1,3-二氢-2H-苯并咪唑-2-硫酮
  参考文献：
  名称：

  Fischer,O., Chemische Berichte, 1893, vol. 26, p. 190

  摘要：

  DOI：

文献信息

• Fischer,O., Chemische Berichte, 1893, vol. 26, p. 190
  作者：Fischer,O.

  DOI：——

  日期：——
• Proline bis-amides as potent dual orexin receptor antagonists
  作者：Jeffrey M. Bergman、Anthony J. Roecker、Swati P. Mercer、Rodney A. Bednar、Duane R. Reiss、Richard W. Ransom、C. Meacham Harrell、Douglas J. Pettibone、Wei Lemaire、Kathy L. Murphy、Chunze Li、Thomayant Prueksaritanont、Christopher J. Winrow、John J. Renger、Kenneth S. Koblan、George D. Hartman、Paul J. Coleman

  DOI：10.1016/j.bmcl.2008.01.001

  日期：2008.2

  A series of OX2R/OX1R dual orexin antagonists was prepared based on a proline bis-amide identified as a screening lead. Through a combination of classical and library synthesis, potency enhancing replacements for both amide portions were discovered. N-methylation of the benzimidazole moiety within the lead structure significantly reduced P-gp susceptibility while increasing potency, giving rise to good brain penetration. A compound from this series has demonstrated in vivo central activity when dosed peripherally in a pharmacodynamic model of orexin activity. Published by Elsevier Ltd.