N-[(4E)-4-[(4-methoxy-3,5-dimethylphenyl)methylidene]-6-methyl-5-oxo-1H-imidazo[4,5-d]azepin-2-yl]-N-methylformamide | 1254361-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[(4E)-4-[(4-methoxy-3,5-dimethylphenyl)methylidene]-6-methyl-5-oxo-1H-imidazo[4,5-d]azepin-2-yl]-N-methylformamide
• CAS: 1254361-86-8
• 化学式: C₂₀H₂₂N₄O₃
• 分子量: 366.42
• InChiKey: XFKOCIFKYOKGRS-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(4E)-4-[(4-methoxy-3,5-dimethylphenyl)methylidene]-6-methyl-5-oxo-1H-imidazo[4,5-d]azepin-2-yl]-N-methylformamide 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.08h， 以10 mg的产率得到4-(4-methoxy-3,5-dimethylbenzyl)-6-methyl-2-(methylamino)-imidazo[4,5-d]azepin-5(6H)-one
  参考文献：
  名称：

  Synthetic Analogues of the Microtubule-Stabilizing Sponge Alkaloid Ceratamine A Are More Active than the Natural Product

  摘要：

  Desbromoceratamine A (3) exhibits significantly less potent activity than the natural product ceratamine A (1) in a cell-based assay for antimitotic activity. Synthesis of the ceratamine A analogue 4 has shown that replacing the bromine atoms in the natural product with methyl groups generates an analogue that is more active than natural ceratamine A (1). Further enhancement of the antimitotic activity of the ceratamine pharmacophore has been achieved in the synthetic analogue 33, which has both bromine atoms replaced with methyl groups and an additional methyl substituent on the amino nitrogen at C-2. An efficient synthetic route has been developed to 33 that should enable the first in vivo evaluation of the new ceratamine microtubule-stabilizing pharmacophore and has provided several additional analogues for structure-activity relationship evaluation.

  DOI：

  10.1021/jm101012q
• 作为产物：
  描述：

  (E)-N-(1-((benzyloxy)methyl)-8-(4-methoxy-3,5-dimethylbenzylidene)-6-methyl-7-oxo-1,6,7,8-tetrahydroimidazo[4,5-d]azepin-2-yl)-N-methylformamide 在 aluminum (III) chloride 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 N-[(4E)-4-[(4-methoxy-3,5-dimethylphenyl)methylidene]-6-methyl-5-oxo-1H-imidazo[4,5-d]azepin-2-yl]-N-methylformamide
  参考文献：
  名称：

  Synthetic Analogues of the Microtubule-Stabilizing Sponge Alkaloid Ceratamine A Are More Active than the Natural Product

  摘要：

  Desbromoceratamine A (3) exhibits significantly less potent activity than the natural product ceratamine A (1) in a cell-based assay for antimitotic activity. Synthesis of the ceratamine A analogue 4 has shown that replacing the bromine atoms in the natural product with methyl groups generates an analogue that is more active than natural ceratamine A (1). Further enhancement of the antimitotic activity of the ceratamine pharmacophore has been achieved in the synthetic analogue 33, which has both bromine atoms replaced with methyl groups and an additional methyl substituent on the amino nitrogen at C-2. An efficient synthetic route has been developed to 33 that should enable the first in vivo evaluation of the new ceratamine microtubule-stabilizing pharmacophore and has provided several additional analogues for structure-activity relationship evaluation.

  DOI：

  10.1021/jm101012q