ethyl 2-[4-(bromoacetyl)-3-methylphenoxy]-2-methylpropionate | 400641-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-[4-(bromoacetyl)-3-methylphenoxy]-2-methylpropionate
• CAS: 400641-58-9
• 化学式: C₁₅H₁₉BrO₄
• 分子量: 343.217
• InChiKey: KMKDDXBKWGLOIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  416.3±35.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[4-(bromoacetyl)-3-methylphenoxy]-2-methylpropionate 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 1.0h， 生成 ethyl 2-[4-(2-bromoethyl)-3-methylphenoxy]-2-methylpropionate
  参考文献：
  名称：

  β3-Adrenoceptor agonists for the treatment of frequent urination and urinary incontinence: 2-[4-(2-{[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)phenoxy]-2-methylpropionic acid

  摘要：

  In a search for novel analogues of beta (3)-adrenoceptor (AR) agonists relaxing the bladder for treatment of urinary dysfunction, 2-[4-(2-{[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)phenoxy]-2-methylpropionic acids (1a-e), into which a fibrate-like structure ha been incorporated, were synthesised. Compound la was found to be a selective beta (3)-AR agonist in functional assays using the ferret detrusor (VAR), rat uterus (beta (2)-AR), and rat atrium (beta (1)-AR): beta (3): EC50 = 7.8 nM, beta (2): IC50 = 7,300 nM, beta (1): EC20 = 23,000 nM. The introduction of a chlorine atom or methyl substituent at the ortho-position on the phenyl ring of la further improved VAR selectivity. In an in vivo study, la lowered intrabladder pressure (ED50 = 31 mug/kg) in rats, without increasing heart rate, in keeping with the in vitro results. Consequently, it is proposed that la and its analogues (1b e), possess beta (3)-AR agonistic activity in the absence of undesirable beta (1)- or beta (2)-AR mediated actions. and may be useful for clinical treatment and pharmacological studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00240-1
• 作为产物：
  描述：

  间甲酚 在 sodium hydroxide 、 三氯化铝 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 12.0h， 生成 ethyl 2-[4-(bromoacetyl)-3-methylphenoxy]-2-methylpropionate
  参考文献：
  名称：

  β3-Adrenoceptor agonists for the treatment of frequent urination and urinary incontinence: 2-[4-(2-{[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)phenoxy]-2-methylpropionic acid

  摘要：

  In a search for novel analogues of beta (3)-adrenoceptor (AR) agonists relaxing the bladder for treatment of urinary dysfunction, 2-[4-(2-{[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino}ethyl)phenoxy]-2-methylpropionic acids (1a-e), into which a fibrate-like structure ha been incorporated, were synthesised. Compound la was found to be a selective beta (3)-AR agonist in functional assays using the ferret detrusor (VAR), rat uterus (beta (2)-AR), and rat atrium (beta (1)-AR): beta (3): EC50 = 7.8 nM, beta (2): IC50 = 7,300 nM, beta (1): EC20 = 23,000 nM. The introduction of a chlorine atom or methyl substituent at the ortho-position on the phenyl ring of la further improved VAR selectivity. In an in vivo study, la lowered intrabladder pressure (ED50 = 31 mug/kg) in rats, without increasing heart rate, in keeping with the in vitro results. Consequently, it is proposed that la and its analogues (1b e), possess beta (3)-AR agonistic activity in the absence of undesirable beta (1)- or beta (2)-AR mediated actions. and may be useful for clinical treatment and pharmacological studies. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00240-1