噻吩并[3,2-d]嘧啶-2,4(1H,3H)-二酮,3-[2-[4-(4-氟苯甲酰)-1-哌啶基]乙基]- | 123195-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 噻吩并[3,2-d]嘧啶-2,4(1H,3H)-二酮,3-[2-[4-(4-氟苯甲酰)-1-哌啶基]乙基]-
• 英文名称: 3-<2-<4-(4-fluorobenzoyl)piperidin-1-yl>ethyl>thieno<3,2-d>pyrimidine-2,4-dione
• 英文别名: 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]thieno[3,2-d]pyrimidine-2,4-dione；3-[2-[4-(4-Fluorobenzoyl)-1-piperidinyl]ethyl]thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione；3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-1H-thieno[3,2-d]pyrimidine-2,4-dione
• CAS: 123195-24-4
• 化学式: C₂₀H₂₀FN₃O₃S
• 分子量: 401.462
• InChiKey: GOEBTRPECAZGTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：

  噻吩并[3,2-d]嘧啶-2,4(1H,3H)-二酮,3-[2-[4-(4-氟苯甲酰)-1-哌啶基]乙基]- 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-[2-[4-(4-Fluorobenzoyl)piperidin-1-yl]ethyl]-1-methylthieno[3,2-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-(2-carbomethoxythien-3-yl)-N'-<2-<4-(4-fluorobenzoyl)piperidin-1-yl>ethyl>urea 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以94%的产率得到噻吩并[3,2-d]嘧啶-2,4(1H,3H)-二酮,3-[2-[4-(4-氟苯甲酰)-1-哌啶基]乙基]-
  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

• PRESS, JEFFERY B.;RUSSELL, RONALD K.
  作者：PRESS, JEFFERY B.、RUSSELL, RONALD K.

  DOI：——

  日期：——
• JPH01213284A
  申请人：——

  公开号：JPH01213284A

  公开（公告）日：1989-08-28
• US4835157A
  申请人：——

  公开号：US4835157A

  公开（公告）日：1989-05-30