methyl 2-[3-(acetylamino)-6-methyl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl]acetate | 274925-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七噻吩
• 英文名称: methyl 2-[3-(acetylamino)-6-methyl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl]acetate
• CAS: 274925-53-0
• 化学式: C₁₄H₁₇NO₄S
• 分子量: 295.359
• InChiKey: PBKVLWCLHZLQSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[3-(acetylamino)-6-methyl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl]acetate 在 一水合肼 作用下， 反应 0.5h， 以90.4%的产率得到N-(4a-Methyl-3-oxo-2,3,4,4a,5,6-hexahydro-thieno[3,2-h]cinnolin-7-yl)-acetamide
  参考文献：
  名称：

  Preparation of Thieno[3,2-h]cinnolinones as Matrix Metalloproteinase Inhibitors

  摘要：

  A new series of thieno[3,2-h]cinnolinone analogues was synthesized which is structurally related to 2,3,4,4a,5,6-hexahydro thieno[3,2-h]cinnolin-3-one 1, a weak inhibitor of the matrix metalloproteinase MMP-8 (human neutrophil collagenase). Preliminary SAR studies have shown that while C-4a-methyl, C-7-acetylamino, C-7 and C-8-nitro substitution, and C-4-C-4a olefination provided no increase in activity relative to 1, Cs-acetylamino substitution as in 5 and 8 was favourable. Moreover, to predict how the thieno[3,3-h]cinnolinone inhibitors might bind to MMP-8, the unsubstituted compound 9 was docked into the MMP-8 crystal structure. These studies revealed that inhibitor 9 does not seem to be able to coordinate the catalytically-active zinc ion but preferably interact with the peptide-binding region of the active site.

  DOI：

  10.1002/(sici)1521-4184(200002)333:2/3<37::aid-ardp37>3.0.co;2-v
• 作为产物：
  描述：

  methyl 2-(6-methyl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl)acetate 在 硫酸 、 铁粉 、 potassium nitrate 作用下， 以 溶剂黄146 为溶剂， 反应 9.0h， 生成 methyl 2-[3-(acetylamino)-6-methyl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophen-6-yl]acetate
  参考文献：
  名称：

  Preparation of Thieno[3,2-h]cinnolinones as Matrix Metalloproteinase Inhibitors

  摘要：

  A new series of thieno[3,2-h]cinnolinone analogues was synthesized which is structurally related to 2,3,4,4a,5,6-hexahydro thieno[3,2-h]cinnolin-3-one 1, a weak inhibitor of the matrix metalloproteinase MMP-8 (human neutrophil collagenase). Preliminary SAR studies have shown that while C-4a-methyl, C-7-acetylamino, C-7 and C-8-nitro substitution, and C-4-C-4a olefination provided no increase in activity relative to 1, Cs-acetylamino substitution as in 5 and 8 was favourable. Moreover, to predict how the thieno[3,3-h]cinnolinone inhibitors might bind to MMP-8, the unsubstituted compound 9 was docked into the MMP-8 crystal structure. These studies revealed that inhibitor 9 does not seem to be able to coordinate the catalytically-active zinc ion but preferably interact with the peptide-binding region of the active site.

  DOI：

  10.1002/(sici)1521-4184(200002)333:2/3<37::aid-ardp37>3.0.co;2-v