propyl N-(2-pyrrol-1-ylthiophen-3-yl)carbamate | 1026422-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: propyl N-(2-pyrrol-1-ylthiophen-3-yl)carbamate
• CAS: 1026422-54-7
• 化学式: C₁₂H₁₄N₂O₂S
• 分子量: 250.321
• InChiKey: GVCPDMVOHLVZNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  propyl N-(2-pyrrol-1-ylthiophen-3-yl)carbamate 在 吡啶 、 sodium hydroxide 、 potassium carbonate 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.0h， 生成 8-[[4-[(4-Fluorophenyl)methyl]piperazin-1-yl]methyl]-3-thia-1,7-diazatricyclo[7.3.0.02,6]dodeca-2(6),4,7,9,11-pentaene
  参考文献：
  名称：

  Novel Selective and Partial Agonists of 5-HT₃ Receptors. Part 1. Synthesis and Biological Evaluation of Piperazinopyrrolothienopyrazines

  摘要：

  A series of piperazinopyrrolo[1,2-a]thieno[3,2-e]- and -[2,3-e]pyrazine derivatives were prepared and evaluated in order to determine the necessary requirements for high affinity on the 5-HT3 receptors and high selectivity versus other 5-HT receptor subtypes. Various substitutions on the piperazine and the thiophene ring of the pyrrolothienopyrazine moieties were systematically explored as well as replacement of the piperazine by other cyclic amines. The best compounds are in the nanomolar range of affinity for 5-HT3 receptors with high to very high selectivity (up to 10 000 for 14b). These high-affinity compounds have in common a benzyl- or allylpiperazine substituent with no substitutions on the thiophene ring. Five of these compounds (1a, 4b, 13a,b, and 14b) have been evaluated on the Von Bezold-Jarisch reflex and were characterized as partial agonists. One of them, 13a, has shown in vivo at very low dose a potent anxiolytic-like activity in the light/dark test.

  DOI：

  10.1021/jm950543x
• 作为产物：
  描述：

  2-(1H-吡咯-1-基)噻吩-3-羧酸 在 sodium azide 、 TEA 、 氯甲酸乙酯 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 2.0h， 生成 propyl N-(2-pyrrol-1-ylthiophen-3-yl)carbamate
  参考文献：
  名称：

  Novel Selective and Partial Agonists of 5-HT₃ Receptors. Part 1. Synthesis and Biological Evaluation of Piperazinopyrrolothienopyrazines

  摘要：

  A series of piperazinopyrrolo[1,2-a]thieno[3,2-e]- and -[2,3-e]pyrazine derivatives were prepared and evaluated in order to determine the necessary requirements for high affinity on the 5-HT3 receptors and high selectivity versus other 5-HT receptor subtypes. Various substitutions on the piperazine and the thiophene ring of the pyrrolothienopyrazine moieties were systematically explored as well as replacement of the piperazine by other cyclic amines. The best compounds are in the nanomolar range of affinity for 5-HT3 receptors with high to very high selectivity (up to 10 000 for 14b). These high-affinity compounds have in common a benzyl- or allylpiperazine substituent with no substitutions on the thiophene ring. Five of these compounds (1a, 4b, 13a,b, and 14b) have been evaluated on the Von Bezold-Jarisch reflex and were characterized as partial agonists. One of them, 13a, has shown in vivo at very low dose a potent anxiolytic-like activity in the light/dark test.

  DOI：

  10.1021/jm950543x