2-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridine | 570386-39-9

• 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: 2-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridine
• 英文别名: (E)-2-(6-methoxy-3-nitropyridin-2-yl)-N,N-dimethylethenamine
• CAS: 570386-39-9
• 化学式: C₁₀H₁₃N₃O₃
• 分子量: 223.232
• InChiKey: WHFIQZOQUXUTSN-VOTSOKGWSA-N

物化性质

• 沸点：
  365.0±42.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridine 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 100.0h， 生成 5-methoxy-3-(1-methylpiperidin-4-yl)pyrrolo[3,2-b]pyridine
  参考文献：
  名称：

  Novel Potent 5-HT_1F Receptor Agonists:  Structure−Activity Studies of a Series of Substituted N-[3-(1-Methyl-4-piperidinyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]amides

  摘要：

  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.

  DOI：

  10.1021/jm030020m
• 作为产物：
  描述：

  2-甲氧基-5-硝基-6-甲基吡啶 在 N,N-二甲基甲酰胺二甲基缩醛 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-Methoxy-5-Nitro-6-(2-Dimethylaminoethen-1-yl)pyridine
  参考文献：
  名称：

  5-HT1F agonists

  摘要：

  本发明涉及以下化合物（I）的化合物或其药用酸盐；该化合物对于激活哺乳动物体内的5-HT1f受体和抑制蛋白外渗具有用处。

  公开号：

  US06358972B1

文献信息

• [EN] PPAR ACTIVE COMPOUNDS<br/>[FR] COMPOSES AYANT UNE ACTIVITE SUR DES PPAR
  申请人：PLEXXIKON INC

  公开号：WO2005009958A1

  公开（公告）日：2005-02-03

  Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.

  描述了对PPARs具有活性的化合物，包括全活性化合物。还描述了开发或识别具有所需选择性配置文件的化合物的方法。
• PPAR ACTIVE COMPOUNDS
  申请人：Arnold James

  公开号：US20080045581A1

  公开（公告）日：2008-02-21

  Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.

  描述了对PPARs活性的化合物，包括全面活性的化合物。还描述了开发或识别具有所需选择性配置文件的化合物的方法。
• PPAR active compounds
  申请人：Arnold James

  公开号：US20080096913A1

  公开（公告）日：2008-04-24

  Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.

  描述了对PPARs活性的化合物，包括全谱活性化合物。还描述了开发或鉴定具有所需选择性配置文件的化合物的方法。
• 5-HT1F AGONISTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1089993B1

  公开（公告）日：2003-10-22
• US6358972B1
  申请人：——

  公开号：US6358972B1

  公开（公告）日：2002-03-19