(E)-(S)-4-(3-biphenyl-4-yl-ureido)-5-phenyl-pent-2-enoic acid (2-dimethylamino-ethyl)-amide | 760214-13-9

• 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: (E)-(S)-4-(3-biphenyl-4-yl-ureido)-5-phenyl-pent-2-enoic acid (2-dimethylamino-ethyl)-amide
• 英文别名: (E,4S)-N-[2-(dimethylamino)ethyl]-5-phenyl-4-[(4-phenylphenyl)carbamoylamino]pent-2-enamide
• CAS: 760214-13-9
• 化学式: C₂₈H₃₂N₄O₂
• 分子量: 456.588
• InChiKey: UNPQTFJHQRKQSM-VRAYXWLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-(S)-4-(3-biphenyl-4-yl-ureido)-5-phenyl-pent-2-enoic acid (2-dimethylamino-ethyl)-amide 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Novel glycine transporter type-2 reuptake inhibitors. Part 2: β- and γ-amino acid derivatives

  摘要：

  Several beta- and gamma-amino acid derivatives were prepared as glycine transport inhibitors and their ability to block the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter-2 (hGlyT-2) were evaluated. A range of lipophilic side chains were tolerated in the beta-amino acid series (i.e., Ph, CH2Ph, CH(CH3)(2), and CH2CH(CH3)(2)). In the gamma-amino acid series, minimal differences in potency were observed between the alpha, beta-unsaturated analogs and the corresponding saturated derivatives. In both series, a 4-biphenyl or 4-phenoxyphenyl substituent appended to the urea or cyanogunaidine moiety was necessary for in vitro activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.043
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 在 盐酸 、 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.25h， 生成 (E)-(S)-4-(3-biphenyl-4-yl-ureido)-5-phenyl-pent-2-enoic acid (2-dimethylamino-ethyl)-amide
  参考文献：
  名称：

  Novel glycine transporter type-2 reuptake inhibitors. Part 2: β- and γ-amino acid derivatives

  摘要：

  Several beta- and gamma-amino acid derivatives were prepared as glycine transport inhibitors and their ability to block the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter-2 (hGlyT-2) were evaluated. A range of lipophilic side chains were tolerated in the beta-amino acid series (i.e., Ph, CH2Ph, CH(CH3)(2), and CH2CH(CH3)(2)). In the gamma-amino acid series, minimal differences in potency were observed between the alpha, beta-unsaturated analogs and the corresponding saturated derivatives. In both series, a 4-biphenyl or 4-phenoxyphenyl substituent appended to the urea or cyanogunaidine moiety was necessary for in vitro activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.043

文献信息

• [EN] GLYT2 MODULATORS<br/>[FR] MODULATEURS DU GLYT2
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005044810A1

  公开（公告）日：2005-05-19

  α-, β-, and Ϝ-amino acid derivatives of formula I are disclosed as selective GlyT2 inhibitors for the treatment of central nervous system (CNS) conditions such as muscle spasticity, tinnitus, epilepsy and neuropathic pain. Formula I

  公式I的α-, β-, 和 Ϝ-氨基酸衍生物被披露为选择性GlyT2抑制剂，用于治疗中枢神经系统（CNS）疾病，如肌肉痉挛、耳鸣、癫痫和神经痛。
• US7202269B2
  申请人：——

  公开号：US7202269B2

  公开（公告）日：2007-04-10
• Novel glycine transporter type-2 reuptake inhibitors. Part 2: β- and γ-amino acid derivatives
  作者：Ronald L Wolin、Alejandro Santillán、Tristin Barclay、Liu Tang、Hariharan Venkatesan、Sandy Wilson、Doo Hyun Lee、Timothy W Lovenberg

  DOI：10.1016/j.bmc.2004.05.043

  日期：2004.8

  Several beta- and gamma-amino acid derivatives were prepared as glycine transport inhibitors and their ability to block the uptake of [C-14]-glycine in COS7 cells transfected with human glycine transporter-2 (hGlyT-2) were evaluated. A range of lipophilic side chains were tolerated in the beta-amino acid series (i.e., Ph, CH2Ph, CH(CH3)(2), and CH2CH(CH3)(2)). In the gamma-amino acid series, minimal differences in potency were observed between the alpha, beta-unsaturated analogs and the corresponding saturated derivatives. In both series, a 4-biphenyl or 4-phenoxyphenyl substituent appended to the urea or cyanogunaidine moiety was necessary for in vitro activity. (C) 2004 Elsevier Ltd. All rights reserved.