Ethyl 2-{[(4-chlorophenoxy)acetyl]amino}-4,5-dimethylthiophene-3-carboxylate | 314047-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: Ethyl 2-{[(4-chlorophenoxy)acetyl]amino}-4,5-dimethylthiophene-3-carboxylate
• 英文别名: ethyl 2-[[2-(4-chlorophenoxy)acetyl]amino]-4,5-dimethylthiophene-3-carboxylate
• CAS: 314047-21-7
• 化学式: C₁₇H₁₈ClNO₄S
• mdl: MFCD00851757
• 分子量: 367.853
• InChiKey: RXWXWKFVDHAZOU-UHFFFAOYSA-N

物化性质

• 沸点：
  540.8±50.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-{[(4-chlorophenoxy)acetyl]amino}-4,5-dimethylthiophene-3-carboxylate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 3-Amino-2-[(4-chlorophenoxy)methyl]-5,6-dimethylthieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Design, synthesis and antihistaminic (H1) activity of some condensed 3-aminopyrimidin-4(3H)-ones

  摘要：

  A novel series of condensed 3-amino-2-(substituted)methylpyrimidin-4(3H)-ones is reported with potential H-1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA(2) value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect thr antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00128-8
• 作为产物：
  描述：

  对氯苯氧乙酸 在 氯化亚砜 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 1.0h， 生成 Ethyl 2-{[(4-chlorophenoxy)acetyl]amino}-4,5-dimethylthiophene-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and antihistaminic (H1) activity of some condensed 3-aminopyrimidin-4(3H)-ones

  摘要：

  A novel series of condensed 3-amino-2-(substituted)methylpyrimidin-4(3H)-ones is reported with potential H-1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA(2) value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect thr antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00128-8

文献信息

• Design, synthesis and antihistaminic (H1) activity of some condensed 3-aminopyrimidin-4(3H)-ones
  作者：C Shishoo

  DOI：10.1016/s0223-5234(00)00128-8

  日期：2000.3

  A novel series of condensed 3-amino-2-(substituted)methylpyrimidin-4(3H)-ones is reported with potential H-1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA(2) value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect thr antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.