Benzyl 4-(4-fluoro-2-methylsulfanylphenyl)-4-hydroxypiperidine-1-carboxylate | 439942-28-6

• 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: Benzyl 4-(4-fluoro-2-methylsulfanylphenyl)-4-hydroxypiperidine-1-carboxylate
• CAS: 439942-28-6
• 化学式: C₂₀H₂₂FNO₃S
• 分子量: 375.464
• InChiKey: FKJXMKIBDKYUKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  75.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl 4-(4-fluoro-2-methylsulfanylphenyl)-4-hydroxypiperidine-1-carboxylate 在 titanium(IV) isopropylate 、 三乙基硅烷 、 叔丁基过氧化氢 、 D-(-)-酒石酸二乙酯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl 4-[4-fluoro-2-[(S)-methylsulfinyl]phenyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and SAR of Tachykinin Antagonists:  Modulation of Balance in NK₁/NK₂ Receptor Antagonist Activity

  摘要：

  Through optimization of compounds based on the dual NK1/NK2 antagonist ZD6021, it was found that alteration of two key regions could modulate the balance of NK1 and NK2 potency. Substitution of the 2-naphthalene position in analogues of ZD6021 resulted in increased NK1 potency and thus afforded NK1 preferential antagonists. Alterations of the piperidine region could then increase NK2 potency to restore dual NK1/NK2 selectivity. Through these efforts, three novel receptor antagonists from a single chemically related series were identified; two are dual NK1/NK2 antagonists, and the third is an NK1 preferential antagonist. In this paper, the factors affecting the balance of NK1 and NK2 selectivity in this series are discussed and the in vitro and in vivo properties of the novel antagonists are described.

  DOI：

  10.1021/jm020094i
• 作为产物：
  描述：

  2-溴-5-氟苯酚 在 三乙烯二胺 、 氢氧化钾 、 正丁基锂 、 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Benzyl 4-(4-fluoro-2-methylsulfanylphenyl)-4-hydroxypiperidine-1-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and SAR of Tachykinin Antagonists:  Modulation of Balance in NK₁/NK₂ Receptor Antagonist Activity

  摘要：

  Through optimization of compounds based on the dual NK1/NK2 antagonist ZD6021, it was found that alteration of two key regions could modulate the balance of NK1 and NK2 potency. Substitution of the 2-naphthalene position in analogues of ZD6021 resulted in increased NK1 potency and thus afforded NK1 preferential antagonists. Alterations of the piperidine region could then increase NK2 potency to restore dual NK1/NK2 selectivity. Through these efforts, three novel receptor antagonists from a single chemically related series were identified; two are dual NK1/NK2 antagonists, and the third is an NK1 preferential antagonist. In this paper, the factors affecting the balance of NK1 and NK2 selectivity in this series are discussed and the in vitro and in vivo properties of the novel antagonists are described.

  DOI：

  10.1021/jm020094i

文献信息

• Compounds
  申请人：——

  公开号：US20040058916A1

  公开（公告）日：2004-03-25

  A compound having general formula 1 and methods of using such compounds for the treatment of diseases and pharmaceutical composition comprising such compounds.

  一种具有一般式1的化合物，以及使用这种化合物治疗疾病的方法和包含这种化合物的药物组合物。
• COMPOUNDS
  申请人：AstraZeneca AB

  公开号：EP1345899A1

  公开（公告）日：2003-09-24
• N-substituted amides as NK1 receptor antagonists
  申请人：AstraZeneca AB

  公开号：EP1345899B1

  公开（公告）日：2009-01-14
• US7064136B2
  申请人：——

  公开号：US7064136B2

  公开（公告）日：2006-06-20
• [EN] COMPOUNDS<br/>[FR] COMPOSES
  申请人：ASTRAZENECA AB

  公开号：WO2002051807A1

  公开（公告）日：2002-07-04

  A compound having general formula (I), and methods of using such compounds for the treatment of diseases and pharmaceutical composition comprising such compounds.