methyl 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridin-3-yl)propanoate | 1335061-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridin-3-yl)propanoate
• CAS: 1335061-29-4
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: YJFSUSLERSOYJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridin-3-yl)propanoate 在 lithium hydroxide monohydrate 作用下， 以 甲醇 为溶剂， 以77%的产率得到3-(6-methoxy-2-phenylimidazo[1,2-a]pyridin-3-yl)propanoic acid
  参考文献：
  名称：

  Design and synthesis of 2-phenylimidazo[1,2-a]pyridines as a novel class of melatonin receptor ligands

  摘要：

  A novel class of imidazo[1,2-a]pyridines as melatonin receptor ligands is designed and synthesized. The affinities of 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-N-methyl-propionamide 8, N-[2-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-ethyl]-acetamide 13 and N-(1-hydroxy-3-(5-methoxy-2-phenyl-1H-indol-3-yl)propan-2-yl)acetamide 18 are evaluated for binding on melatonin receptors. Compound 8 present good selectivity for MT2 over MT1 (MT1/MT2 = 19) and compound 13 have good affinities for both MT1 (Ki :28 nM) and MT2 (Ki : 8 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.030
• 作为产物：
  描述：

  (E)-methyl 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridin-3-yl)acrylate 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 以80%的产率得到methyl 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridin-3-yl)propanoate
  参考文献：
  名称：

  Design and synthesis of 2-phenylimidazo[1,2-a]pyridines as a novel class of melatonin receptor ligands

  摘要：

  A novel class of imidazo[1,2-a]pyridines as melatonin receptor ligands is designed and synthesized. The affinities of 3-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-N-methyl-propionamide 8, N-[2-(6-methoxy-2-phenylimidazo[1,2-a]pyridine-3-yl)-ethyl]-acetamide 13 and N-(1-hydroxy-3-(5-methoxy-2-phenyl-1H-indol-3-yl)propan-2-yl)acetamide 18 are evaluated for binding on melatonin receptors. Compound 8 present good selectivity for MT2 over MT1 (MT1/MT2 = 19) and compound 13 have good affinities for both MT1 (Ki :28 nM) and MT2 (Ki : 8 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.030