4-chloro-1-{4-[4-(2-methoxyphenyl)-1-piperazinyl]butyl}indolin-2-one

• 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: 4-chloro-1-{4-[4-(2-methoxyphenyl)-1-piperazinyl]butyl}indolin-2-one
• 英文别名: 4-chloro-1-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3H-indol-2-one
• 化学式: C₂₃H₂₈ClN₃O₂
• 分子量: 413.947
• InChiKey: ABVQUUBGQQUJDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯-2-氧化吲哚 在 TEA 、 potassium carbonate 作用下， 以 乙腈 、 苯 为溶剂， 反应 20.0h， 生成 4-chloro-1-{4-[4-(2-methoxyphenyl)-1-piperazinyl]butyl}indolin-2-one
  参考文献：
  名称：

  A Search for New 5-HT1A/5-HT2A Receptor Ligands. In Vitro and in vivo Studies of 1-[ω-(4-Aryl-1-piperazinyl)alkyl]indolin-2(1H)-ones

  摘要：

  A series of 1-{omega-(4-aryl-1-piperazinyl)alkyl]indolin-2(1H)-one derivatives 2-14 was synthesized in order to obtain ligands with a dual 5-HT1A/5-HT2A activity. The majority of those compounds (2-5, 7, 10-13) exhibited a high 5-HT1A (K-i = 2 - 44 nM) and/or 5-HT2A affinity (K-i = 51 and 39 for 5 and 7, respectively). Induction of lower lip retraction (LLR) and behavioral syndrome and inhibition of these efects evoked by 8-hydroxy-2-(di-n-propyl-amino)tetralin (8-OH-DPAT) were used for determination the agonistic and antagonistic activity, respectively, at 5-HT1A receptors. The 5-HT2A antagonistic activity was assessed by the blocking effect on the head twitches induced by (+/-)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) in mice. Two of the tested compounds, 1-{3-[4-(3-chlorophenyl)-1-piperazinyl]propyl}-6-fluoroindolin-2(1H)-one (5) and 1-{3-[4-(2-methoxyphenyl)-1 piperazinyl]propyl}indolin-2(1H)-one (7), demonstrated a high 5-HT1A/5-HT2A affinity and an in vivo antagonistic activity towards both receptor subtypes.

  DOI：

  10.1002/(sici)1521-4184(199810)331:10<325::aid-ardp325>3.0.co;2-6

文献信息

• A Search for New 5-HT1A/5-HT2A Receptor Ligands. In Vitro and in vivo Studies of 1-[ω-(4-Aryl-1-piperazinyl)alkyl]indolin-2(1H)-ones
  作者：Maria J. Mokrosz、Beata Duszyńska、Stanisław Misztal、Aleksandra Kłodzińska、Ewa Tatarczyńska、Ewa Chojnacka-Wójcik、Marta Dziedzicka-Wasylewska

  DOI：10.1002/(sici)1521-4184(199810)331:10<325::aid-ardp325>3.0.co;2-6

  日期：1998.10

  A series of 1-omega-(4-aryl-1-piperazinyl)alkyl]indolin-2(1H)-one derivatives 2-14 was synthesized in order to obtain ligands with a dual 5-HT1A/5-HT2A activity. The majority of those compounds (2-5, 7, 10-13) exhibited a high 5-HT1A (K-i = 2 - 44 nM) and/or 5-HT2A affinity (K-i = 51 and 39 for 5 and 7, respectively). Induction of lower lip retraction (LLR) and behavioral syndrome and inhibition of these efects evoked by 8-hydroxy-2-(di-n-propyl-amino)tetralin (8-OH-DPAT) were used for determination the agonistic and antagonistic activity, respectively, at 5-HT1A receptors. The 5-HT2A antagonistic activity was assessed by the blocking effect on the head twitches induced by (+/-)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) in mice. Two of the tested compounds, 1-3-[4-(3-chlorophenyl)-1-piperazinyl]propyl}-6-fluoroindolin-2(1H)-one (5) and 1-3-[4-(2-methoxyphenyl)-1 piperazinyl]propyl}indolin-2(1H)-one (7), demonstrated a high 5-HT1A/5-HT2A affinity and an in vivo antagonistic activity towards both receptor subtypes.