5-[4-(1-Propan-2-ylpiperidin-4-yl)oxyphenyl]-3,4-diazabicyclo[4.1.0]hept-4-en-2-one | 1569020-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[4-(1-Propan-2-ylpiperidin-4-yl)oxyphenyl]-3,4-diazabicyclo[4.1.0]hept-4-en-2-one
• 英文别名: 5-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,4-diazabicyclo[4.1.0]hept-4-en-2-one
• CAS: 1569020-36-5
• 化学式: C₁₉H₂₅N₃O₂
• 分子量: 327.426
• InChiKey: ODCFXBPEVBNSRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-Phenoxy-1-propan-2-ylpiperidine 在 aluminum (III) chloride 、 肼 作用下， 以 1,2-二氯乙烷 、 异丙醇 为溶剂， 生成 5-[4-(1-Propan-2-ylpiperidin-4-yl)oxyphenyl]-3,4-diazabicyclo[4.1.0]hept-4-en-2-one
  参考文献：
  名称：

  Discovery of (1R,6S)-5-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-4-en-2-one (R,S-4a): Histamine H3 receptor inverse agonist demonstrating potent cognitive enhancing and wake promoting activity

  摘要：

  A series of fused cyclopropyl-4,5-dihydropyridazin-3-one (3,4-diaza-bicyclo[4.1.0] hept-4-en-2-one) phenoxypiperidine analogs was designed and synthesized, leading to the identification of (1R, 6S)-5[ 4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3,4-diaza-bicyclo[4.1.0] hept-4-en-2-one (R, S-4a) as a secondgeneration pyridazin-3-one H3R antagonist. Compound R, S-4a was a potent H3R functional antagonist in vivo in the rat dipsogenia model, demonstrated potent wake activity in the rat EEG/EMG model, and enhanced short-term memory in the rat social recognition memory model at doses as low as 0.03-0.3 mg/kg po. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.061

文献信息

• Discovery of (1R,6S)-5-[4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3,4-diaza-bicyclo[4.1.0]hept-4-en-2-one (R,S-4a): Histamine H3 receptor inverse agonist demonstrating potent cognitive enhancing and wake promoting activity
  作者：Robert L. Hudkins、Kurt A. Josef、Nadine C. Becknell、Lisa D. Aimone、Jacquelyn A. Lyons、Joanne R. Mathiasen、John A. Gruner、Rita Raddatz

  DOI：10.1016/j.bmcl.2014.01.061

  日期：2014.3

  A series of fused cyclopropyl-4,5-dihydropyridazin-3-one (3,4-diaza-bicyclo[4.1.0] hept-4-en-2-one) phenoxypiperidine analogs was designed and synthesized, leading to the identification of (1R, 6S)-5[ 4-(1-cyclobutyl-piperidin-4-yloxy)-phenyl]-3,4-diaza-bicyclo[4.1.0] hept-4-en-2-one (R, S-4a) as a secondgeneration pyridazin-3-one H3R antagonist. Compound R, S-4a was a potent H3R functional antagonist in vivo in the rat dipsogenia model, demonstrated potent wake activity in the rat EEG/EMG model, and enhanced short-term memory in the rat social recognition memory model at doses as low as 0.03-0.3 mg/kg po. (C) 2014 Elsevier Ltd. All rights reserved.