3-<2-<4-(4-fluorobenzoyl)piperidin-1-yl>ethyl>thieno<3,4-d>pyrimidine-2,4-dione | 130501-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-<2-<4-(4-fluorobenzoyl)piperidin-1-yl>ethyl>thieno<3,4-d>pyrimidine-2,4-dione
• 英文别名: 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,4-d]pyrimidine-2,4-dione；3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-1H-thieno[3,4-d]pyrimidine-2,4-dione
• CAS: 130501-99-4
• 化学式: C₂₀H₂₀FN₃O₃S
• 分子量: 401.462
• InChiKey: BFLDBQJLWNSNDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  98
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-<2-<4-(4-fluorobenzoyl)piperidin-1-yl>ethyl>thieno<3,4-d>pyrimidine-2,4-dione 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以15%的产率得到1-acetyl-3-<2-<4-(4-fluorobenzoyl)piperidin-1-yl>ethyl>thieno<3,4-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
• 作为产物：
  描述：

  N-(3-carbomethoxythien-4-yl)-N'-(2-chloroethyl)urea 在 sodium hydroxide 、 碳酸氢钠 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 120.0h， 生成 3-<2-<4-(4-fluorobenzoyl)piperidin-1-yl>ethyl>thieno<3,4-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

• Ring-fused thienopyrimidinedione derivatives
  申请人：Ortho Pharmaceutical Corporation

  公开号：US04939137A1

  公开（公告）日：1990-07-03

  The synthesis of ring-fused thienopyrimidinedione derivatives is described. The novel ring-fused thienopyrimidinedione derivatives are generally vasodilating agents and antihypertensive agents and as such are useful as cardiovascular agents.

  本文描述了环融合噻吩嘧啶二酮衍生物的合成。这些新型的环融合噻吩嘧啶二酮衍生物通常是血管扩张剂和降压药物，因此可用作心血管药物。
• 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
• US4939137A
  申请人：——

  公开号：US4939137A

  公开（公告）日：1990-07-03
• 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.