N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-(trifluoromethyl)cinnamamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-(trifluoromethyl)cinnamamide
• 英文别名: N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-trifluoromethyl-cinnamic amide；(E)-N-[3-(dimethylamino)-1-naphthalen-2-ylpropyl]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide
• 化学式: C₂₅H₂₅F₃N₂O
• 分子量: 426.482
• InChiKey: ZNHDEMOCOCFLIC-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(二甲氨基)-1-萘-2-基丙烷-1-酮 在 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 204.0h， 生成 N-[3-dimethylamino-1-(2-naphthyl)propyl]-4-(trifluoromethyl)cinnamamide
  参考文献：
  名称：

  Design, parallel synthesis and SAR of novel urotensin II receptor agonists

  摘要：

  A 30-membered library of amides based on the potent urotensin II (UII) receptor agonist FL104, has been synthesized from ten different carboxylic acids and three amines. A synthetic protocol producing the amides in 47-98% yield has been developed in which the purification involved only extractions and in a few cases filtration through an ion-exchange resin. It was found that 5 mg of starting material was enough to obtain reproducible results and excellent purities. Thus, the procedure is estimated to be transferable to fully automated systems. The synthesized compounds were evaluated for their Ull receptor agonistic activities using a cell-based assay (R-SAT). The most active compounds were the 4-trifluoromethylcinnamic amides of 1-(4-chlorophenyt)-3-dimethylamino-propylamine and 1-(2-naphthyl)-3-dimethylamino-propylamine, both showed EC50 values of 130 nM. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.015

文献信息

• WO2006/135694
  申请人：——

  公开号：——

  公开（公告）日：——
• Design, parallel synthesis and SAR of novel urotensin II receptor agonists
  作者：Fredrik Lehmann、Lisa Lake、Erika A. Currier、Roger Olsson、Uli Hacksell、Kristina Luthman

  DOI：10.1016/j.ejmech.2006.09.015

  日期：2007.2

  A 30-membered library of amides based on the potent urotensin II (UII) receptor agonist FL104, has been synthesized from ten different carboxylic acids and three amines. A synthetic protocol producing the amides in 47-98% yield has been developed in which the purification involved only extractions and in a few cases filtration through an ion-exchange resin. It was found that 5 mg of starting material was enough to obtain reproducible results and excellent purities. Thus, the procedure is estimated to be transferable to fully automated systems. The synthesized compounds were evaluated for their Ull receptor agonistic activities using a cell-based assay (R-SAT). The most active compounds were the 4-trifluoromethylcinnamic amides of 1-(4-chlorophenyt)-3-dimethylamino-propylamine and 1-(2-naphthyl)-3-dimethylamino-propylamine, both showed EC50 values of 130 nM. (c) 2006 Elsevier Masson SAS. All rights reserved.