ethyl N-benzyl-N-[4-(2-bromoethyl)phenyl]-aminoacetate | 344285-74-1

• 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: ethyl N-benzyl-N-[4-(2-bromoethyl)phenyl]-aminoacetate
• 英文别名: ethyl 2-[N-benzyl-4-(2-bromoethyl)anilino]acetate
• CAS: 344285-74-1
• 化学式: C₁₉H₂₂BrNO₂
• 分子量: 376.293
• InChiKey: GGJGGESVWSRUJR-UHFFFAOYSA-N

物化性质

• 沸点：
  478.4±40.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl N-benzyl-N-[4-(2-bromoethyl)phenyl]-aminoacetate 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 [Benzyl-(4-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-amino]-acetic acid
  参考文献：
  名称：

  Discovery of Novel N-Phenylglycine Derivatives as Potent and Selective β₃-Adrenoceptor Agonists for the Treatment of Frequent Urination and Urinary Incontinence

  摘要：

  With a novel assay using isolated ferret detrusor to estimate beta (3)-adrenoceptor agonistic activity, we found that a series of glycine derivatives of ritodrine, a beta (2)-adrenoceptor agonist, are potent beta (3)-adrenoceptor agonists, with excellent selectivity versus beta1 and beta (2) subtypes. Substitution of halogens in the phenyl ring increased potency and selectivity for the beta (3)-adrenoceptor, and this was dependent upon the position of the halogens. The chlorine-substituted derivatives 3f-i exhibited potent beta (3)-adrenoceptor-mediated relaxation of ferret detrusor (EC50 = 0.93, 11, 14, and 160 nM) and higher potency at beta (3)-adrenoceptors than at beta (1) or beta (2) The intravenous administration of 3h significantly reduced the urinary bladder pressure in anesthetized male rats (ED50 = 48 mug/kg) without cardiovascular side effects. This article is the first report of structure-activity relationships (SAR) concerning beta (3)-adrenoceptor agonists as agents for the treatment of urinary frequency and incontinence.

  DOI：

  10.1021/jm000455z
• 作为产物：
  描述：

  4-氨基苯乙醇 在 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 ethyl N-benzyl-N-[4-(2-bromoethyl)phenyl]-aminoacetate
  参考文献：
  名称：

  Discovery of Novel N-Phenylglycine Derivatives as Potent and Selective β₃-Adrenoceptor Agonists for the Treatment of Frequent Urination and Urinary Incontinence

  摘要：

  With a novel assay using isolated ferret detrusor to estimate beta (3)-adrenoceptor agonistic activity, we found that a series of glycine derivatives of ritodrine, a beta (2)-adrenoceptor agonist, are potent beta (3)-adrenoceptor agonists, with excellent selectivity versus beta1 and beta (2) subtypes. Substitution of halogens in the phenyl ring increased potency and selectivity for the beta (3)-adrenoceptor, and this was dependent upon the position of the halogens. The chlorine-substituted derivatives 3f-i exhibited potent beta (3)-adrenoceptor-mediated relaxation of ferret detrusor (EC50 = 0.93, 11, 14, and 160 nM) and higher potency at beta (3)-adrenoceptors than at beta (1) or beta (2) The intravenous administration of 3h significantly reduced the urinary bladder pressure in anesthetized male rats (ED50 = 48 mug/kg) without cardiovascular side effects. This article is the first report of structure-activity relationships (SAR) concerning beta (3)-adrenoceptor agonists as agents for the treatment of urinary frequency and incontinence.

  DOI：

  10.1021/jm000455z