benzyl-{2-[2-(3-benzyl-ureido)-phenylamino]-ethyl}-carbamic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl-{2-[2-(3-benzyl-ureido)-phenylamino]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-benzyl-N-[2-[2-(benzylcarbamoylamino)anilino]ethyl]carbamate
• 化学式: C₂₈H₃₄N₄O₃
• 分子量: 474.603
• InChiKey: YSPQELPVGWRCCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl-{2-[2-(3-benzyl-ureido)-phenylamino]-ethyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 1-benzyl-3-[2-(2-benzylamino-ethylamino)-phenyl]-urea
  参考文献：
  名称：

  Inhibitors of the glycine transporter type-2 (GlyT-2): synthesis and biological activity of benzoylpiperidine derivatives

  摘要：

  A series of benzoylpiperidine analogs related to 4a was prepared, and their ability to inhibit the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter type-2 (GlyT-2) was evaluated. Small structural changes to the benzoylpiperidine region of the molecule led to a significant decrease in GlyT-2 inhibitory activity. In contrast, the distal aryl ring was more tolerant to functional group modifications and could accommodate a variety of substitutes at the C-2 or C-3 positions. Comparable activities to 4a were obtained by replacing the anilino nitrogen with an ether linkage 27 or by exchanging the isopropoxy ether moiety with an isopropyl amino group 15. A distinct preference for a 2-carbon tether (n = 1) was observed relative to the corresponding 3-carbon homolog (n = 2). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.044
• 作为产物：
  描述：

  N-苄基乙二胺 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 benzyl-{2-[2-(3-benzyl-ureido)-phenylamino]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Inhibitors of the glycine transporter type-2 (GlyT-2): synthesis and biological activity of benzoylpiperidine derivatives

  摘要：

  A series of benzoylpiperidine analogs related to 4a was prepared, and their ability to inhibit the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter type-2 (GlyT-2) was evaluated. Small structural changes to the benzoylpiperidine region of the molecule led to a significant decrease in GlyT-2 inhibitory activity. In contrast, the distal aryl ring was more tolerant to functional group modifications and could accommodate a variety of substitutes at the C-2 or C-3 positions. Comparable activities to 4a were obtained by replacing the anilino nitrogen with an ether linkage 27 or by exchanging the isopropoxy ether moiety with an isopropyl amino group 15. A distinct preference for a 2-carbon tether (n = 1) was observed relative to the corresponding 3-carbon homolog (n = 2). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.044

文献信息

• Aryl piperidine amides
  申请人：Huang Q. Charles

  公开号：US20050049239A1

  公开（公告）日：2005-03-03

  The invention provides novel GlyT2 inhibiting compounds useful in modulating, treating, or preventing: anxiolytic disorders; a condition requiring treatment of injured mammalian nerve tissue; a condition amenable to treatment through administration of a neurotrophic factor; a neurological disorder; or obesity; an obesity-related disorder.

  该发明提供了新颖的GlyT2抑制化合物，可用于调节、治疗或预防：焦虑症；需要治疗受伤哺乳动物神经组织的状况；适合通过神经营养因子管理治疗的状况；神经系统紊乱；或肥胖症；与肥胖相关的疾病。
• Aryl Piperidine Amides
  申请人：Huang Q. Charles

  公开号：US20080009521A1

  公开（公告）日：2008-01-10

  The invention provides novel GlyT2 inhibiting compounds useful in modulating, treating, or preventing: anxiolytic disorders; a condition requiring treatment of injured mammalian nerve tissue; a condition amenable to treatment through administration of a neurotrophic factor; a neurological disorder; or obesity; an obesity-related disorder.

  本发明提供了新型GlyT2抑制化合物，可用于调节、治疗或预防：抗焦虑障碍；需要治疗受损哺乳动物神经组织的状况；可通过给予神经营养因子进行治疗的状况；神经系统疾病；或肥胖症；肥胖相关疾病。
• ARYL PIPERIDINE AMIDES
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1660472A1

  公开（公告）日：2006-05-31
• US7276610B2
  申请人：——

  公开号：US7276610B2

  公开（公告）日：2007-10-02
• US7915420B2
  申请人：——

  公开号：US7915420B2

  公开（公告）日：2011-03-29