ethyl 2-(4-(4-(5-nitro-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl)acetate | 1448669-99-5

• 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: ethyl 2-(4-(4-(5-nitro-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl)acetate
• 英文别名: ethyl 2-[4-[4-(6-nitro-1H-benzimidazol-2-yl)phenyl]cyclohexyl]acetate
• CAS: 1448669-99-5
• 化学式: C₂₃H₂₅N₃O₄
• 分子量: 407.469
• InChiKey: WZMFSQMVOTYKGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-(4-(5-nitro-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl)acetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以79%的产率得到2-(4-(4-(5-amino-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl)acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of aminobenzimidazole derivatives with a phenylcyclohexyl acetic acid group as anti-obesity and anti-diabetic agents

  摘要：

  A series of benzimidazole derivatives with a phenylcyclohexyl acetic acid group as DGAT-1 inhibitors was developed. Among the benzimidazole series, compound 5k showed submicromolar in vitro activity toward human and mouse DGAT-1, good selectivity toward DGAT-2, human liver metabolic stability, and pharmacokinetic (PK) and safety profiles such as hERG, CYP and acute toxicity. Additionally, 5k showed good in vivo efficacy in 4 weeks study with DIO mouse model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.081
• 作为产物：
  描述：

  ethyl 2-(4-phenylcyclohexylidene)acetate 在 palladium 10% on activated carbon 、 Oxone 、 氢气 、 四氯化钛 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 ethyl 2-(4-(4-(5-nitro-1H-benzo[d]imidazol-2-yl)phenyl)cyclohexyl)acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of aminobenzimidazole derivatives with a phenylcyclohexyl acetic acid group as anti-obesity and anti-diabetic agents

  摘要：

  A series of benzimidazole derivatives with a phenylcyclohexyl acetic acid group as DGAT-1 inhibitors was developed. Among the benzimidazole series, compound 5k showed submicromolar in vitro activity toward human and mouse DGAT-1, good selectivity toward DGAT-2, human liver metabolic stability, and pharmacokinetic (PK) and safety profiles such as hERG, CYP and acute toxicity. Additionally, 5k showed good in vivo efficacy in 4 weeks study with DIO mouse model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.081

文献信息

• Synthesis and biological evaluation of aminobenzimidazole derivatives with a phenylcyclohexyl acetic acid group as anti-obesity and anti-diabetic agents
  作者：Hyun Jung Kwak、Yu Mi Pyun、Ji Young Kim、Haushabhau S. Pagire、Ki Young Kim、Kwang Rok Kim、Sang Dal Rhee、Won Hoon Jung、Jin Sook Song、Myung Ae Bae、Duck Hyung Lee、Jin Hee Ahn

  DOI：10.1016/j.bmcl.2013.05.081

  日期：2013.8

  A series of benzimidazole derivatives with a phenylcyclohexyl acetic acid group as DGAT-1 inhibitors was developed. Among the benzimidazole series, compound 5k showed submicromolar in vitro activity toward human and mouse DGAT-1, good selectivity toward DGAT-2, human liver metabolic stability, and pharmacokinetic (PK) and safety profiles such as hERG, CYP and acute toxicity. Additionally, 5k showed good in vivo efficacy in 4 weeks study with DIO mouse model. (C) 2013 Elsevier Ltd. All rights reserved.