(5-butyryl-thiophen-2-yl)-acetic acid ethyl ester | 105475-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-butyryl-thiophen-2-yl)-acetic acid ethyl ester
• 英文别名: 5-Butyryl-thienyl-(2)-essigsaeure-aethylester；Ethyl 2-(5-butanoylthiophen-2-yl)acetate
• CAS: 105475-97-6
• 化学式: C₁₂H₁₆O₃S
• 分子量: 240.323
• InChiKey: CGPXWFBECXPHIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5-butyryl-thiophen-2-yl)-acetic acid ethyl ester 在 盐酸 、 三乙基硅烷 、 甲酸 、 Noyori's catalyst 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.5h， 生成 (S)-2-hydroxy-3-methoxy-10-n-butyl-5,8,12,12a-tetrahydro-6H-benzo[a]thieno[3,2-g]quinolizine
  参考文献：
  名称：

  Design, synthesis and evaluation of benzo[a]thieno[3,2-g]quinolizines as novel l-SPD derivatives possessing dopamine D1, D2 and serotonin 5-HT1A multiple action profiles

  摘要：

  A novel scaffold derived from l-SPD with a substituted thiophene group in the D ring were designed, synthesized, and evaluated for their binding affinities at dopamine (D-1, D-2 and D-3) and serotonin (5-HT1A and 5-HT2A) receptors. Most of the tetracyclic compounds exhibited higher affinities for D-2 and 5-HT1A receptors than l-SPD, while compound 23e showed the highest K-i value of 7.54 nM at D-2 receptor which was 14 times more potent than l-SPD. Additionally, compounds 23d and 23e were more potent than l-SPD at D-3 receptor. According to the functional assays, 23d and 23e were demonstrated as full antagonists at D-1 and D-2 receptors and full agonists at 5-HT1A receptor. Since the combination of D-2 antagonism and 5-HT1A agonism is considered effective in treating both the positive and negative symptoms of schizophrenia, these novel compounds are implicated as potential therapeutic agents. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.09.024
• 作为产物：
  描述：

  2-噻吩乙酸乙酯 、 丁酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (5-butyryl-thiophen-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis and evaluation of benzo[a]thieno[3,2-g]quinolizines as novel l-SPD derivatives possessing dopamine D1, D2 and serotonin 5-HT1A multiple action profiles

  摘要：

  A novel scaffold derived from l-SPD with a substituted thiophene group in the D ring were designed, synthesized, and evaluated for their binding affinities at dopamine (D-1, D-2 and D-3) and serotonin (5-HT1A and 5-HT2A) receptors. Most of the tetracyclic compounds exhibited higher affinities for D-2 and 5-HT1A receptors than l-SPD, while compound 23e showed the highest K-i value of 7.54 nM at D-2 receptor which was 14 times more potent than l-SPD. Additionally, compounds 23d and 23e were more potent than l-SPD at D-3 receptor. According to the functional assays, 23d and 23e were demonstrated as full antagonists at D-1 and D-2 receptors and full agonists at 5-HT1A receptor. Since the combination of D-2 antagonism and 5-HT1A agonism is considered effective in treating both the positive and negative symptoms of schizophrenia, these novel compounds are implicated as potential therapeutic agents. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.09.024