(E)-5-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}pyrazolo[1,5-a]pyridine-3-carbaldehyde oxime | 1060726-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (E)-5-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}pyrazolo[1,5-a]pyridine-3-carbaldehyde oxime
• 英文别名: (s-trans) 5-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy]pyrazolo[1,5-a]pyridine-3-carbaldehyde oxime；(s-trans)-5-[4-[4-(2,3-Dichlorophenyl)piperazin-1-yl]butoxy]pyrazolo[1,5-a]pyridin-3-carbaldehyde oxime；s-cis isomer of (E)-5-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)pyrazolo[1,5-a]pyridine-3-carbaldehyde oxime；(NE)-N-[[5-[4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy]pyrazolo[1,5-a]pyridin-3-yl]methylidene]hydroxylamine
• CAS: 1060726-55-7
• 化学式: C₂₂H₂₅Cl₂N₅O₂
• 分子量: 462.379
• InChiKey: DWMNREQVNSYYID-WGOQTCKBSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  65.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-5-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}pyrazolo[1,5-a]pyridine-3-carbaldehyde oxime 在 乙酸酐 作用下， 反应 8.0h， 以72%的产率得到5-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}pyrazolo[1,5-a]pyridine-3-carbonitrile
  参考文献：
  名称：

  Indolizines and aza-analog derivatives thereof as CNS active compounds

  摘要：

  目前披露的是具有医疗用途的通式为的基于吲哚啉的化合物，例如作为抗精神病药物。

  公开号：

  EP1972628A1
• 作为产物：
  描述：

  1H-pyrazolo[1,5-a]pyridin-5-one 在 盐酸 、 盐酸羟胺 、 potassium carbonate 、 sodium iodide 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.5h， 生成 (E)-5-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butoxy}pyrazolo[1,5-a]pyridine-3-carbaldehyde oxime
  参考文献：
  名称：

  Functionally Selective Dopamine D₂, D₃Receptor Partial Agonists

  摘要：

  Dopamine D-2 receptor-promoted activation of G alpha(o) over G alpha(i) may increase synaptic plasticity and thereby might improve negative symptoms of schizophrenia. Heterocyclic dopamine surrogates comprising a pyrazolo[1,5-a]pyridine moiety were synthesized and investigated for their binding properties when low- to subnanomolar K-i values were determined for D-2L, D-2S, and D-3 receptors. Measurement of [S-35]GTP gamma S incorporation at D-2S coexpressed with G-protein subunits indicated significant bias for promotion of G alpha(o1) over G alpha(i2) coupling for several test compounds. Functionally selective D-2S activation was most striking for the carbaldoxime 8b (G alpha(o1), pEC(50) = 8.87, E-max = 65%; G alpha(i2), pEC(50) = 6.63, E-max = 27%). In contrast, the investigated 1,4-disubstituted aromatic piperazines (1,4-DAPs) behaved as antagonists for beta-arrestin-2 recruitment, implying significant ligand bias for G-protein activation over beta-arrestin-2 recruitment at D-2S receptors. Ligand efficacy and selectivity between D-2S and D-3 activation were strongly influenced by regiochemistry and the nature of functional groups attached to the pyrazolo[1,5-a]pyridine moiety.

  DOI：

  10.1021/jm5004039

文献信息

• INDOLIZINES AND AZA-ANALOG DERIVATIVES THEREOF AS CNS ACTIVE COMPOUNDS
  申请人：Gmeiner Peter

  公开号：US20100168125A1

  公开（公告）日：2010-07-01

  The present application relates to indolizine-based compounds of the general formula (I) and aza-analogs thereof, which have medical utility, for example as antipsychotics.

  本申请涉及基于吲哚嗪的化合物的一般式(I)和其氮杂环类似物，这些化合物具有医学效用，例如作为抗精神病药物。
• [EN] INDOLIZINES AND AZA-ANALOG DERIVATIVES THEREOF AS CNS ACTIVE COMPOUNDS<br/>[FR] INDOLIZINES ET DÉRIVÉS ANALOGUES AZA DE CELLES-CI EN TANT QUE COMPOSÉS ACTIFS SUR LE SYSTÈME NERVEUX CENTRAL
  申请人：SANOL ARZNEI SCHWARZ GMBH

  公开号：WO2008113559A2

  公开（公告）日：2008-09-25

  [EN] The present application relates to indolizine-based compounds of the general formula (I) and aza-analogs thereof, which have medical utility, for example as antipsychotics.
  [FR] La présente invention porte sur des composés à base d'indolizine de la formule générale (I) et sur les analogues aza de ceux-ci, qui ont une utilité médicale, par exemple comme antipsychotiques.