N,N-dimethyl-N'-[4-(2-(dimethylamino)vinyl)-5-nitropyridin-2-yl]formamidine | 570384-98-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N,N-dimethyl-N'-[4-(2-(dimethylamino)vinyl)-5-nitropyridin-2-yl]formamidine
• 英文别名: N'-[4-((E)-2-dimethylamino-vinyl)-5-nitro-pyridin-2-yl]-N,N-dimethyl-formamidine；N'-[4-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-2-yl]-N,N-dimethylmethanimidamide
• CAS: 570384-98-4
• 化学式: C₁₂H₁₇N₅O₂
• 分子量: 263.299
• InChiKey: JTBOVZHIKRHDDA-OOLRQUSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-N'-[4-(2-(dimethylamino)vinyl)-5-nitropyridin-2-yl]formamidine 在 钯 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以to yield N,N-dimethyl-N′-(1H-pyrrolo[2,3-c]pyridin-5-yl)-formamidine (6.19 g, 105%) as a dark solid的产率得到N,N-dimethyl-N'-(1H-pyrrolo[2,3-c]pyridin-5-yl)formamidine
  参考文献：
  名称：

  Indazole compounds

  摘要：

  本发明涉及一种化合物(I)或其药学上可接受的盐、前药和生物活性代谢物，其中取代基如本文所定义，该化合物可用作治疗剂。

  公开号：

  US08008481B2
• 作为产物：
  描述：

  2-氨基-4-甲基-5-硝基吡啶 、 N,N-二甲基甲酰胺二甲基缩醛 反应 96.0h， 以to afford N′-[4-((E)-2-Dimethylamino-vinyl)-5-nitro-pyridin-2-yl]-N,N-dimethyl-formamidine (8.36 g, 101%) as a dark solid, RP HPLC (Table 1, Method e) Rt=1.62, m/z的产率得到N,N-dimethyl-N'-[4-(2-(dimethylamino)vinyl)-5-nitropyridin-2-yl]formamidine
  参考文献：
  名称：

  Indazole Compounds

  摘要：

  本发明涉及化合物(I)或其药学上可接受的盐、前药和生物活性代谢物，其中取代基的定义如本文所述，这些化合物可用作治疗剂。

  公开号：

  US20120053345A1

文献信息

• Novel Potent 5-HT_1F Receptor Agonists:  Structure−Activity Studies of a Series of Substituted <i>N</i>-[3-(1-Methyl-4-piperidinyl)-1<i>H</i>-pyrrolo[3,2-<i>b</i>]pyridin-5-yl]amides
  作者：Sandra A. Filla、Brian M. Mathes、Kirk W. Johnson、Lee A. Phebus、Marlene L. Cohen、David L. Nelson、John M. Zgombick、Jon A. Erickson、Kathryn W. Schenck、David B. Wainscott、Theresa A. Branchek、John M. Schaus

  DOI：10.1021/jm030020m

  日期：2003.7.1

  Compound 1a (LY334370), a selective 5-HT1F receptor agonist (SSOFRA), inhibited dural inflammation in the neurogenic plasma protein extravasation model of migraine and demonstrated clinical efficacy for the acute treatment of migraine. Although 1 was greater than 100-fold selective over both the 5-HT1B and 5-HT1D receptors, it exhibited appreciable 5-HT1A receptor affinity. Described here is the synthesis and evaluation of a series of pyrrolo[2,3-c]pyridine and pyrrolo[3,2-b]pyridine (2a and 3a) as well as pyrrolo[3,2-d]pyrimidine (4a) analogues of 1, compounds prepared in an effort to identify SSOFRAs with improved selectivity over other 5-HT1 receptor subtypes. The pyrrolo [3,2-b] pyridine analogue 3a showed high 5-HT1F receptor affinity but offered no improvement in selectivity compared to 1. However, the C-5 acetamide derivative, 3b, was greater than 100-fold selective over the 5-HT1A, 5-HT1B, and 5-HT1D receptors. SAR studies of this series determined that alkylamides in particular exhibited high selectivity for the 5-HT1F receptor. Replacement at C-5 with other substituents decreased affinity or selectivity. These SAR studies identified SSOFRAs that demonstrated oral activity in the neurogenic plasma protein extravasation model, a model indicative of antimigraine activity.