5,5-二噻吩基-2-咪唑烷-2,4-二酮 | 62032-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5,5-二噻吩基-2-咪唑烷-2,4-二酮
• 英文名称: 5,5-di-(2-thienyl)-hydantoin
• 英文别名: 5,5-Bis(2-thienyl)hydantoin；5,5-di-thiophen-2-yl-imidazolidine-2,4-dione；5,5-di-[2]thienyl-imidazolidine-2,4-dione；5,5-Di-[2]thienyl-imidazolidin-2,4-dion；5,5-Dithien-2-ylimidazolidine-2,4-dione；5,5-dithiophen-2-ylimidazolidine-2,4-dione
• CAS: 62032-07-9
• 化学式: C₁₁H₈N₂O₂S₂
• mdl: MFCD07324816
• 分子量: 264.329
• InChiKey: AEBDYALCYLNGHV-UHFFFAOYSA-N

物化性质

• 溶解度：
  >39.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5,5-二噻吩基-2-咪唑烷-2,4-二酮 在 palladium on activated charcoal 盐酸 、 氢气 、 三苯基膦 、 红铝 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 20.0~85.0 ℃ 、137.9 kPa 条件下， 反应 36.0h， 生成 4,4-di-(2-thienyl)-1-(piperidin-4-yl)-imidazolidin-2-one
  参考文献：
  名称：

  Discovery of Diaryl Imidazolidin-2-one Derivatives, a Novel Class of Muscarinic M3 Selective Antagonists (Part 1)

  摘要：

  Pharmacophore-based structural identification, synthesis, and structure-activity relationships of a new class of muscarinic M3 receptor antagonists, the diaryl imidazolidin-2-one derivatives, are described. The versatility of the discovered scaffold allowed for several structural modifications that resulted in the discovery of two distinct classes of compounds, specifically a class of tertiary amine derivatives (potentially useful for the treatment of overactive bladder by oral administration) and a class of quaternary ammonium salt derivatives (potentially useful for the treatment of respiratory diseases by the inhalation route of administration). In this paper, we describe the synthesis and biological activity of tertiary amine derivatives. For these compounds, selectivity for the M3 receptor toward the M2 receptor was crucial, because the M2 receptor subtype is mainly responsible for adverse systemic side effects of currently marketed muscarinic antagonists. Compound 50 showed the highest selectivity versus M2 receptor, with binding affinity for M3 receptor K-i = 4.8 nM and for M2 receptor K-i = 1141 nM. Functional in vitro studies on selected compounds confirmed the antagonist activity toward the M3 receptor and functional selectivity toward the M2 receptor.

  DOI：

  10.1021/jm061159a
• 作为产物：
  描述：

  双(2-噻吩)酮 、 氰化钾 在 碳酸氢铵 、 尿素 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5,5-二噻吩基-2-咪唑烷-2,4-二酮
  参考文献：
  名称：

  Hydantoins as antitumor agents

  摘要：

  A series of 27 hydantoins was prepared and tested as antitumor agents. These were variously substituted in the 5 position but with special emphasis on the substituents (chloro, acetyl, chloroacetyl, and methyl) in the 1 and/or 3 positions. The most active compound was 5,5-bis(4-chlorophenyl)-1,3-dichlorohydantoin with a T/C value of 190% against P-388 lymphocytic leukemia in mice.

  DOI：

  10.1021/jm00214a031

文献信息

• 5, 5-di-(alpha-thienyl)hydantoin and method for obtaining same
  申请人：PARKE DAVIS & CO

  公开号：US02468168A1

  公开（公告）日：1949-04-26
• Hydantoins as Anticonvulsants. I. 5-R-5-(2-Thienyl)-hydantoins¹
  作者：James J. Spurlock

  DOI：10.1021/ja01101a031

  日期：1953.3