1-acetyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[2,3-d]pyrimidine-2,4-dione | 123195-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-acetyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[2,3-d]pyrimidine-2,4-dione
• CAS: 123195-29-9
• 化学式: C₂₂H₂₂FN₃O₄S
• 分子量: 443.499
• InChiKey: UDOGGVUZISHJJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(3-carboethoxythien-2-yl)-N'-(2-chloroethyl)urea 在 sodium hydroxide 、 碳酸氢钠 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 144.0h， 生成 1-acetyl-3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[2,3-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Thiophene systems. 12. Analogues of ketanserin and ritanserin as selective 5-HT2 antagonists

  摘要：

  A series of thieno[3,2-d]-, [3,4-d]- and [2,3-d]pyrimidinedione derivatives was prepared with N-3 substitution containing the side chains of ketanserin and ritanserin. The best of these thiophene analogues were the isosteres of ketanserin which were up to 20-fold more potent than the standards in 5-HT2 binding assays. More importantly, in addition to their increased potency, these derivatives were more selective than the standards in that they had less affinity for 5-HT1A and alpha-1 binding sites. This selectivity is especially noted as the ratio of alpha-1/5-HT2 wherein the most interesting thiophene isostere (2) in this study had a binding selectivity > 12-fold of ketanserin or ritanserin.

  DOI：

  10.1016/0223-5234(91)90007-a

文献信息

• Thieno- and furopyrimidine-2,4-dione piperidine derivatives as serotonin
  申请人：Ortho Pharmaceutical Corporation

  公开号：US04835157A1

  公开（公告）日：1989-05-30

  Novel thienopyrimidine-2,4-dione piperidine derivatives and novel furo[3,4-d]pyrimidine-2,4-dione piperidine derivatives are described. The novel piperidine derivatives are selective serotonin antagonists and alpha adrenergic blocking agents with cardiovascular, gastrointestinal and central nervous system activites.

  本文描述了新型噻吩嘧啶-2,4-二酮哌啶衍生物和新型呋喃[3,4-d]嘧啶-2,4-二酮哌啶衍生物。这些新型哌啶衍生物是选择性5-羟色胺拮抗剂和α肾上腺素受体阻滞剂，具有心血管、胃肠和中枢神经系统活性。
• US4835157A
  申请人：——

  公开号：US4835157A

  公开（公告）日：1989-05-30
• Thiophene systems. 12. Analogues of ketanserin and ritanserin as selective 5-HT2 antagonists
  作者：JB Press、RK Russell、JJ McNally、RA Rampulla、R Falotico、C Scott、JB Moore、SJ Offord、J Tobia

  DOI：10.1016/0223-5234(91)90007-a

  日期：1991.11

  A series of thieno[3,2-d]-, [3,4-d]- and [2,3-d]pyrimidinedione derivatives was prepared with N-3 substitution containing the side chains of ketanserin and ritanserin. The best of these thiophene analogues were the isosteres of ketanserin which were up to 20-fold more potent than the standards in 5-HT2 binding assays. More importantly, in addition to their increased potency, these derivatives were more selective than the standards in that they had less affinity for 5-HT1A and alpha-1 binding sites. This selectivity is especially noted as the ratio of alpha-1/5-HT2 wherein the most interesting thiophene isostere (2) in this study had a binding selectivity > 12-fold of ketanserin or ritanserin.