3-(4-(2-(1,7'-dimethyl-2'-propyl-1H,3H'-2,5'-bibenzo[d]imidazol-3'-yl)ethoxy)phenyl)acrylonitrile | 1207604-15-6

• 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-(4-(2-(1,7'-dimethyl-2'-propyl-1H,3H'-2,5'-bibenzo[d]imidazol-3'-yl)ethoxy)phenyl)acrylonitrile
• 英文别名: 3-[4-[2-[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]ethoxy]phenyl]prop-2-enenitrile
• CAS: 1207604-15-6
• 化学式: C₃₀H₂₉N₅O
• 分子量: 475.593
• InChiKey: WOVRYZXYYHRCMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-(2-(1,7'-dimethyl-2'-propyl-1H,3H'-2,5'-bibenzo[d]imidazol-3'-yl)ethoxy)phenyl)acrylonitrile 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以93%的产率得到3-(4-(2-(1,7'-dimethyl-2'-propyl-1H,3H'-2,5'-bibenzo[d]imidazol-3'-yl)ethoxy)phenyl)propanenitrile
  参考文献：
  名称：

  Design, Synthesis, and Docking Studies of Novel Benzimidazoles for the Treatment of Metabolic Syndrome

  摘要：

  In addition to lowering blood pressure, telmisartan, an angiotensin (AT,) receptor blocker, has recently been shown to exert pleiotropic effects as a partial agonist of nuclear peroxisome proliferator-activated receptor gamma (PPAR gamma). On the basis of these findings and docking pose similarity between telmisartan and rosiglitazone in PPAR gamma active site, two classes of benzimidazole derivatives were designed and synthesized as dual PPAR gamma agonist/angiotensin II antagonists for the possible treatment of metabolic syndrome. Compound 4, a bisbenzimidazole derivative showed the best affinity for the AT, receptor with a K-i = 13.4 nM, but it was devoid of PPAR gamma activity. On the other hand 9, a monobenzimidazole derivative, showed the highest activity in PPAR gamma transactivation assay (69% activation) with no affinity for the AT(1) receptor. Docking studies lead to the designing of a molecule with dual activity, 10, with moderate PPAR gamma activity (29%) and affinity for the AT(1) receptor (K-i = 2.5 mu M).

  DOI：

  10.1021/jm901272d
• 作为产物：
  描述：

  2-(1,7'-dimethyl-2'-propyl-1H,3'H-2,5'-bibenzo[d]imidazol-3'-yl)ethyl methanesulfonate 、 3-(4-羟基苯基)-2-丙烯腈 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 以96%的产率得到3-(4-(2-(1,7'-dimethyl-2'-propyl-1H,3H'-2,5'-bibenzo[d]imidazol-3'-yl)ethoxy)phenyl)acrylonitrile
  参考文献：
  名称：

  Design, Synthesis, and Docking Studies of Novel Benzimidazoles for the Treatment of Metabolic Syndrome

  摘要：

  In addition to lowering blood pressure, telmisartan, an angiotensin (AT,) receptor blocker, has recently been shown to exert pleiotropic effects as a partial agonist of nuclear peroxisome proliferator-activated receptor gamma (PPAR gamma). On the basis of these findings and docking pose similarity between telmisartan and rosiglitazone in PPAR gamma active site, two classes of benzimidazole derivatives were designed and synthesized as dual PPAR gamma agonist/angiotensin II antagonists for the possible treatment of metabolic syndrome. Compound 4, a bisbenzimidazole derivative showed the best affinity for the AT, receptor with a K-i = 13.4 nM, but it was devoid of PPAR gamma activity. On the other hand 9, a monobenzimidazole derivative, showed the highest activity in PPAR gamma transactivation assay (69% activation) with no affinity for the AT(1) receptor. Docking studies lead to the designing of a molecule with dual activity, 10, with moderate PPAR gamma activity (29%) and affinity for the AT(1) receptor (K-i = 2.5 mu M).

  DOI：

  10.1021/jm901272d