2-(2-bromopentyl)-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one | 1116690-31-3

• 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: 2-(2-bromopentyl)-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one
• 英文别名: 2-(5-bromo-pentyl)-4-(3,4-dimethoxy-phenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one；2-(5-Bromo-pentyl)-4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one；2-(5-bromopentyl)-4-(3,4-dimethoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1-one
• CAS: 1116690-31-3
• 化学式: C₂₁H₂₇BrN₂O₃
• 分子量: 435.361
• InChiKey: BKWWNLJWEVOUOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-bromopentyl)-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 N-(5-(2-(benzyl(1-(4-((5-(4-(3,4-dimethoxyphenyl)-1-oxo-4a,5,6,7,8,8a-hexahydrophthalazin-2(1H)-yl)pentyl)oxy)phenyl)propan-2-yl)amino)-1-hydroxyethyl)-2-(benzyloxy)phenyl)formamide
  参考文献：
  名称：

  Design, synthesis and evaluation of dual pharmacology β2-adrenoceptor agonists and PDE4 inhibitors

  摘要：

  A novel series of formoterol-phthalazinone hybrids were synthesised and evaluated as dual pharmacology beta(2)-adrenoceptor agonists and PDE4 inhibitors. Most of the hybrids displayed high beta(2)-adrenoceptor agonist and moderate PDE4 inhibitory activities. The most potent compound, (R, R)-11c, exhibited agonist (EC50 = 1.05 nM, pEC(50) = 9.0) and potent PDE4B2 inhibitory activities (IC50 = 0.092 mu M). (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.11.028
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 1.0h， 生成 2-(2-bromopentyl)-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one
  参考文献：
  名称：

  Stereoselective inhibition of serotonin re-uptake and phosphodiesterase by dual inhibitors as potential agents for depression

  摘要：

  Multi-target compounds where more than one functional activity is incorporated into the same molecule may have advantages in treating disease states. Selective serotonin re-uptake inhibitors (SSRIs)(a) (i.e., (R)- and (S)-norfluoxetine) were chemically linked to a PDE4 inhibitor via a five carbon bridge. The new dual PDE4 inhibitor/SSRIs (i.e., (R)-8 and (S)-8) showed moderately potent but highly selective serotonin re-uptake inhibition (IC50 values of 173 and 42 nM, respectively) in vitro. The dual PDE4 inhibitor/SSRIs (R)-8 and (S)-8 also inhibited PDE4D2 (i.e., K-i values of 106 and 253 nM, respectively). Due to the synergistic functional activity, PDE4 inhibitor/SSRIs may be effective in treating diseases such as depression. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.10.065

文献信息

• Compounds effective as beta-2 adrenoreceptor agonists as well pde4-inhibitors
  申请人：——

  公开号：US20030195215A1

  公开（公告）日：2003-10-16

  The compounds of formula I in which Ar 1 , A, R6, R7, R8 and Ar 2 have the meanings as given in the description are novel effective bronchial therapeutics. 1

  式I的化合物中，其中Ar1、A、R6、R7、R8和Ar2的含义如描述所示，是一种新型有效的支气管治疗剂。
• Modulators of Central Nervous System Neurotransmitters
  申请人：Cashman John

  公开号：US20080261967A1

  公开（公告）日：2008-10-23

  Disclosed are agents having pharmacological activity against cellular receptors and intracellular signaling, particularly receptors and signaling pathways of central nervous system (CNS) neurotransmitters. Also disclosed are related methods and compositions for the treatment or prevention of diseases or disorders using the agents.

  本发明涉及具有药理活性的药物，特别是针对细胞受体和细胞内信号传导的药物，尤其是中枢神经系统（CNS）神经递质的受体和信号通路。本发明还涉及使用这些药物的相关方法和组合物，用于治疗或预防疾病或障碍。
• MODULATORS OF CENTRAL NERVOUS SYSTEM NEUROTRANSMITTERS
  申请人：CASHMAN John

  公开号：US20130123253A1

  公开（公告）日：2013-05-16

  Disclosed are agents having pharmacological activity against cellular receptors and intracellular signaling, particularly receptors and signaling pathways of central nervous system (CNS) neurotransmitters. Also disclosed are related methods and compositions for the treatment or prevention of diseases or disorders using the agents.

  本发明涉及一种对细胞受体和细胞内信号传导具有药理活性的药剂，特别是针对中枢神经系统（CNS）神经递质的受体和信号通路。本发明还涉及使用这些药剂的相关方法和组合物，用于治疗或预防疾病或障碍。
• COMPOUNDS EFFECTIVE AS BETA-2-ADRENORECEPTOR AGONISTS AS WELL AS PDE4-INHIBITORS
  申请人：ALTANA Pharma AG

  公开号：EP1296956A1

  公开（公告）日：2003-04-02
• EP1771435A4
  申请人：——

  公开号：EP1771435A4

  公开（公告）日：2008-02-13