ethyl N-[4-(2-bromoethyl)phenyl]-N-ethyloxycarbonylmethylaminoacetate | 344285-73-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-[4-(2-bromoethyl)phenyl]-N-ethyloxycarbonylmethylaminoacetate
• 英文别名: ethyl 2-[4-(2-bromoethyl)-N-(2-ethoxy-2-oxoethyl)anilino]acetate
• CAS: 344285-73-0
• 化学式: C₁₆H₂₂BrNO₄
• 分子量: 372.259
• InChiKey: LZYNDCZAROJOCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-[4-(2-bromoethyl)phenyl]-N-ethyloxycarbonylmethylaminoacetate 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 [Carboxymethyl-(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 2.0h， 生成 ethyl N-[4-(2-bromoethyl)phenyl]-N-ethyloxycarbonylmethylaminoacetate
  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