3-(1-benzyl-piperidin-4-yl)-5,5-diphenyl-imidazolidine-2,4-dione | 895148-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(1-benzyl-piperidin-4-yl)-5,5-diphenyl-imidazolidine-2,4-dione
• 英文别名: 3-(1-benzylpiperidin-4-yl)-5,5-diphenylimidazolidine-2,4-dione
• CAS: 895148-72-8
• 化学式: C₂₇H₂₇N₃O₂
• 分子量: 425.53
• InChiKey: UHYXERRLBRDGAY-UHFFFAOYSA-N

物化性质

• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-benzyl-piperidin-4-yl)-5,5-diphenyl-imidazolidine-2,4-dione 在 palladium on activated charcoal 盐酸 、 氢气 、 红铝 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 30.5h， 生成 3-(1-(3-Methoxybenzyl)-piperidin-4-yl)-5,5-diphenyl-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：

  1-苄基-4-羟基哌啶 、 苯妥英 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 3-(1-benzyl-piperidin-4-yl)-5,5-diphenyl-imidazolidine-2,4-dione
  参考文献：
  名称：

  WO2006/66924

  摘要：

  公开号：

文献信息

• Azole Derivatives With Antimuscarinic Activity
  申请人：Peretto Ilaria

  公开号：US20090005364A1

  公开（公告）日：2009-01-01

  The present invention relates to compounds of formula (I) wherein R1, R2, x, X, Y and B are as defined in the description for the treatment of muscarinic acetylcholine receptor mediated diseases, in particular M3 muscarinic receptor mediated diseases.

  本发明涉及式（I）的化合物，其中R1，R2，x，X，Y和B如所述的描述中所定义，用于治疗肌肉型乙酰胆碱受体介导的疾病，特别是M3肌肉型受体介导的疾病。
• AZOLE DERIVATIVES WITH ANTIMUSCARINIC ACTIVITY
  申请人：CHIESI FARMACEUTICI S.p.A.

  公开号：EP1828163A2

  公开（公告）日：2007-09-05
• [EN] AZOLE DERIVATIVES WITH ANTIMUSCARINIC ACTIVITY<br/>[FR] DERIVES D'AZOLE A ACTIVITE ANTIMUSCARINIQUE
  申请人：CHIESI FARMA SPA

  公开号：WO2006066924A2

  公开（公告）日：2006-06-29

  [EN] The present invention relates to compounds of formula (I) wherein R1, R2, x, X, Y and B are as defined in the description for the treatment of muscarinic acetylcholine receptor mediated diseases, in particular M3 muscarinic receptor mediated diseases.
  [FR] La présente invention a trait à des composés de formule (I), dans laquelle R1, R2, x, X, Y et B sont tels que définis dans la description pour le traitement de maladies causées par l'intermédiaire du récepteur muscarinique à l'acétylcholine, notamment les maladies causées par l'intermédiaire du récepteur muscarinique de type M3.