4-{2-[Methyl-(5-methyl-pyridin-2-yl)-amino]-ethoxy}-benzaldehyde | 1027887-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-{2-[Methyl-(5-methyl-pyridin-2-yl)-amino]-ethoxy}-benzaldehyde
• 英文别名: 4-[2-[Methyl-(5-methylpyridin-2-yl)amino]ethoxy]benzaldehyde
• CAS: 1027887-07-5
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: HKUYCZQBNLIESO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{2-[Methyl-(5-methyl-pyridin-2-yl)-amino]-ethoxy}-benzaldehyde 在 palladium on activated charcoal 氢气 、 哌啶乙酸盐 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 18.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 5-(4-{2-[Methyl-(5-methyl-pyridin-2-yl)-amino]-ethoxy}-benzyl)-thiazolidine-2,4-dione
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017
• 作为产物：
  描述：

  2-氯-5-甲基吡啶 在 sodium hydride 作用下， 反应 33.0h， 生成 4-{2-[Methyl-(5-methyl-pyridin-2-yl)-amino]-ethoxy}-benzaldehyde
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017