methyl 3-(4-((4-methyl-2-propyl-1H-benzo[d]imidazol-1-yl)methyl)phenyl)acrylate | 1207603-90-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 3-(4-((4-methyl-2-propyl-1H-benzo[d]imidazol-1-yl)methyl)phenyl)acrylate
• 英文别名: methyl 3-[4-[(4-methyl-2-propylbenzimidazol-1-yl)methyl]phenyl]prop-2-enoate
• CAS: 1207603-90-4
• 化学式: C₂₂H₂₄N₂O₂
• 分子量: 348.445
• InChiKey: SBOAAKBTMBGNLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-((4-methyl-2-propyl-1H-benzo[d]imidazol-1-yl)methyl)phenyl)acrylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以70%的产率得到methyl 3-(4-((4-methyl-2-propyl-1H-benzo[d]imidazol-1-yl)methyl)phenyl)propanoate
  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：

  1-(4-iodobenzyl)-4-methyl-2-propyl-1H-benzo[d]imidazole 、 丙烯酸甲酯（MA） 在 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 100.0 ℃ 、137.9 kPa 条件下， 反应 0.08h， 以60%的产率得到methyl 3-(4-((4-methyl-2-propyl-1H-benzo[d]imidazol-1-yl)methyl)phenyl)acrylate
  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