N-(1-methyl-4-piperidinyl)-4-anisylhydrazine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(1-methyl-4-piperidinyl)-4-anisylhydrazine
• 英文别名: N-(4-methoxyphenyl)-N-(1-methyl-piperidin-4-yl)-hydrazine；1-(4-Methoxyphenyl)-1-(1-methylpiperidin-4-yl)hydrazine
• 化学式: C₁₃H₂₁N₃O
• 分子量: 235.329
• InChiKey: DBXZQEKHPBXEEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  41.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-methyl-4-piperidinyl)-4-anisylhydrazine 、 乙酰丙酸乙酯 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以71%的产率得到[5-methoxy-2-methyl-1-(1-methyl-piperidin-4-yl)-1H-indol-3-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 2-Methyl-3-indolylacetic Derivatives as Anti-Inflammatory Agents That Inhibit Preferentially Cyclooxygenase 1 without Gastric Damage

  摘要：

  Novel substituted 2-methyl-3-indolylacetic derivatives were synthesized and evaluated for their activity in vitro and in vivo on COX-1 and COX-2. Active compounds were screened to determine their gastrointestinal tolerability in vivo in the rat. Results showed that 3 and 4 preferentially inhibited COX-1 in vitro and in vivo. MD simulations indicated an induced fit for COX-1 but not for COX-2, probably because of a lower plasticity of the latter.

  DOI：

  10.1021/jm0608199
• 作为产物：
  描述：

  4-methoxyphenyl-(1-methyl-piperidin-4-yl)-N-nitrosoamine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以18.7 g的产率得到N-(1-methyl-4-piperidinyl)-4-anisylhydrazine
  参考文献：
  名称：

  Synthesis of 2-Methyl-3-indolylacetic Derivatives as Anti-Inflammatory Agents That Inhibit Preferentially Cyclooxygenase 1 without Gastric Damage

  摘要：

  Novel substituted 2-methyl-3-indolylacetic derivatives were synthesized and evaluated for their activity in vitro and in vivo on COX-1 and COX-2. Active compounds were screened to determine their gastrointestinal tolerability in vivo in the rat. Results showed that 3 and 4 preferentially inhibited COX-1 in vitro and in vivo. MD simulations indicated an induced fit for COX-1 but not for COX-2, probably because of a lower plasticity of the latter.

  DOI：

  10.1021/jm0608199

文献信息

• Synthesis and investigations of double-pharmacophore ligands for treatment of chronic and neuropathic pain
  作者：Ruben Vardanyan、Gokhale Vijay、Gary S. Nichol、Lu Liu、Isuru Kumarasinghe、Peg Davis、Todd Vanderah、Frank Porreca、Josephine Lai、Victor J. Hruby

  DOI：10.1016/j.bmc.2009.05.065

  日期：2009.7

  Acids 9a-f as possible bivalent ligands designed as a structural combination of opioid mu-agonist (Fentanyl) and NSAID ( Indomethacin) activities and produced compounds which were tested as analgesics. The obtained series of compounds exhibits low affinity and activity both at opioid receptors and as cyclooxygenase ( COX) inhibitors. One explanation of the weak opioid activity could be stereochemical peculiarities of these bivalent compounds which differ significantly from the fentanyl skeleton. The absence of significant COX inhibitory properties could be explained by the required substitution of an acyl fragment in the indomethacin structure for 4-piperidyl. Published by Elsevier Ltd.
• Synthesis of 2-Methyl-3-indolylacetic Derivatives as Anti-Inflammatory Agents That Inhibit Preferentially Cyclooxygenase 1 without Gastric Damage
  作者：Elisa Perissutti、Ferdinando Fiorino、Christian Renner、Beatrice Severino、Fiorentina Roviezzo、Lidia Sautebin、Antonietta Rossi、Giuseppe Cirino、Vincenzo Santagada、Giuseppe Caliendo

  DOI：10.1021/jm0608199

  日期：2006.12.1

  Novel substituted 2-methyl-3-indolylacetic derivatives were synthesized and evaluated for their activity in vitro and in vivo on COX-1 and COX-2. Active compounds were screened to determine their gastrointestinal tolerability in vivo in the rat. Results showed that 3 and 4 preferentially inhibited COX-1 in vitro and in vivo. MD simulations indicated an induced fit for COX-1 but not for COX-2, probably because of a lower plasticity of the latter.