1-[6-(4-Benzyl-piperidin-1-ylmethyl)-benzo[1,3]dioxol-5-yl]-3-(3-cyano-phenyl)-urea | 275811-02-4

• 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: 1-[6-(4-Benzyl-piperidin-1-ylmethyl)-benzo[1,3]dioxol-5-yl]-3-(3-cyano-phenyl)-urea
• 英文别名: 1-[6-[(4-benzylpiperidin-1-yl)methyl]-1,3-benzodioxol-5-yl]-3-(3-cyanophenyl)urea
• CAS: 275811-02-4
• 化学式: C₂₈H₂₈N₄O₃
• 分子量: 468.555
• InChiKey: SUPPNJZTOAKITB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[6-(4-Benzyl-piperidin-1-ylmethyl)-benzo[1,3]dioxol-5-yl]-3-(3-cyano-phenyl)-urea 、 碘甲烷 以 乙腈 为溶剂， 以47%的产率得到1-[6-[(4-Benzyl-1-methylpiperidin-1-ium-1-yl)methyl]-1,3-benzodioxol-5-yl]-3-(3-cyanophenyl)urea;iodide
  参考文献：
  名称：

  Discovery and Structure−Activity Relationship of N-(Ureidoalkyl)-Benzyl-Piperidines As Potent Small Molecule CC Chemokine Receptor-3 (CCR3) Antagonists

  摘要：

  Structure-activity relationship (SAR) studies of initial screening hits from our corporate library of compounds and a structurally related series of CCR1 receptor antagonists were used to determine that an N-(alkyl)benzylpiperidine is an essential pharmacophore for selective CCR3 antagonists. Further SAR studies that introduced N-(ureidoalkyl) substituents improved the binding potency of these compounds from the micromolar to the low nanomolar range. This new series of compounds also displays highly potent, in vitro functional CCR3-mediated antagonism of eotaxin-induced Ca2+ mobilization and chemotaxis of human eosinophils.

  DOI：

  10.1021/jm0201767
• 作为产物：
  描述：

  4-苄基哌啶 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、344.75 kPa 条件下， 生成 1-[6-(4-Benzyl-piperidin-1-ylmethyl)-benzo[1,3]dioxol-5-yl]-3-(3-cyano-phenyl)-urea
  参考文献：
  名称：

  Discovery and Structure−Activity Relationship of N-(Ureidoalkyl)-Benzyl-Piperidines As Potent Small Molecule CC Chemokine Receptor-3 (CCR3) Antagonists

  摘要：

  Structure-activity relationship (SAR) studies of initial screening hits from our corporate library of compounds and a structurally related series of CCR1 receptor antagonists were used to determine that an N-(alkyl)benzylpiperidine is an essential pharmacophore for selective CCR3 antagonists. Further SAR studies that introduced N-(ureidoalkyl) substituents improved the binding potency of these compounds from the micromolar to the low nanomolar range. This new series of compounds also displays highly potent, in vitro functional CCR3-mediated antagonism of eotaxin-induced Ca2+ mobilization and chemotaxis of human eosinophils.

  DOI：

  10.1021/jm0201767

文献信息

• [EN] N-UREIDOALKYL-PIPERIDINES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] N-UREIDOALKYL-PIPERIDINES UTILISEES EN TANT QUE MODULATEURS DE L'ACTIVITE DES RECEPTEURS DES CHIMIOKINES
  申请人：DU PONT PHARM CO

  公开号：WO2000035454A1

  公开（公告）日：2000-06-22

  The present application describes modulators of CCR3 of formula (I) or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

  本申请描述了CCR3调节剂的公式(I)或其药学上可接受的盐形式，可用于预防哮喘和其他过敏性疾病。
• N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
  申请人：——

  公开号：US20040006107A1

  公开（公告）日：2004-01-08

  The present application describes modulators of CCR3 of formula (I): 1 or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma and other allergic diseases.

  本申请描述了CCR3的调节剂，其化学式为(I):1或其药学上可接受的盐形式，用于预防哮喘和其他过敏性疾病。
• N-UREIDOALKYL-PIPERIDINES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Du Pont Pharmaceuticals Company

  公开号：EP1140087A1

  公开（公告）日：2001-10-10
• EP1140087A4
  申请人：——

  公开号：EP1140087A4

  公开（公告）日：2002-04-03
• US6492400B1
  申请人：——

  公开号：US6492400B1

  公开（公告）日：2002-12-10