methyl (6-cyano-2-methyl-1-oxo-1,2,3,4-tetrahydronaphth-2-yl)acetate | 133414-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: methyl (6-cyano-2-methyl-1-oxo-1,2,3,4-tetrahydronaphth-2-yl)acetate
• 英文别名: methyl 6-cyano-2-methyl-1-oxo-1,2,3,4-tetrahydro-2-naphthylacetate；Methyl 2-(6-cyano-2-methyl-1-oxo-3,4-dihydronaphthalen-2-yl)acetate
• CAS: 133414-35-4
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: JSVCQHVWIHPONJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (6-cyano-2-methyl-1-oxo-1,2,3,4-tetrahydronaphth-2-yl)acetate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 硫酸 、 氢气 、 溴 、 一水合肼 、 溶剂黄146 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 5.11h， 生成 8-amino-4a-methyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3[2H]-one
  参考文献：
  名称：

  Inotropic, vasodilator and low Km, cAMP-selective, cGMP-inhibited phosphodiesterase (PDE III) inhibitory activities of 4a-methyl-4,4a-dihydro-5H-indeno[1,2-c]pyridazin-3(2H)-ones and 4a-methyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-ones

  摘要：

  Novel 7-substituted-4,4a-dihydro-4a-methyl-5H-indenol[1,2-c]pyridazin-3[2H]-ones and 8-substituted-4a-methylbenzo[h]cinnolin-3[2H]-ones have been synthesized and their PDE III inhibitory, inotropic and vasodilator potencies compared with those of their normethyl analogues and their bicyclic 4,5-dihydro-6-phenylpyridazinone analogues. The structure-activity relationships of the tricyclic pyridazinones differ from those of bicyclic pyridazinones mainly in respect of the effect of introducing the methyl group into the pyridazinone ring. Whilst in the 4,5-dihydro-6-phenylpyridazin-3(2H)-ones, introduction of a 5-methyl group has been widely reported to lead to compounds of significantly greater potency, the novel tricyclic 4a-methylpyridazinones showed similar levels of inotropic, vasodilator and PDE III inhibitory potency to their normethyl analogues. Possible reasons for this difference in behaviour are discussed.

  DOI：

  10.1016/0223-5234(90)90196-a
• 作为产物：
  描述：

  6-cyano-1-oxo-1,2,3,4-tetrahydronaphth-2-yl acetic acid 、 碘甲烷 以 N-甲基乙酰胺 、 二氯甲烷 为溶剂， 生成 methyl (6-cyano-2-methyl-1-oxo-1,2,3,4-tetrahydronaphth-2-yl)acetate
  参考文献：
  名称：

  Tricyclic pyridazinone compounds

  摘要：

  这项发明涉及三环吡啶啉酮化合物，含有这些化合物的药物组合物，以及通过给哺乳动物施用有效量的化合物来刺激心脏活动的方法。该发明的一种化合物是7-羧胺基-4,4a-二氢-4a-甲基-[5H]-茚蒽[1,2-c]-吡啶啉-3[2H]-酮。

  公开号：

  US04755511A1

文献信息

• Tricyclic pyridazinone compounds
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04755511A1

  公开（公告）日：1988-07-05

  This invention relates to tricyclic pyridazinone compounds, pharmaceutical compositions containing the compounds, and a method of stimulating cardiac activity in a mammal by administering an effective amount of the compound. A compound of the invention is 7-carboxamido-4,4a-dihydro-4a-methyl-[5H]-indeno[1,2-c]-pyridazin-3[2H]-on e.

  这项发明涉及三环吡啶啉酮化合物，含有这些化合物的药物组合物，以及通过给哺乳动物施用有效量的化合物来刺激心脏活动的方法。该发明的一种化合物是7-羧胺基-4,4a-二氢-4a-甲基-[5H]-茚蒽[1,2-c]-吡啶啉-3[2H]-酮。
• BAKEWELL, S. J.;COATES, W. J.;COMER, M. B.;REEVES, M. L.;WARRINGTON, B. H+, EUR. J. MED. CHEM., 25,(1990) N, C. 765-774
  作者：BAKEWELL, S. J.、COATES, W. J.、COMER, M. B.、REEVES, M. L.、WARRINGTON, B. H+

  DOI：——

  日期：——
• Heterocyclic compounds
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0181145B1

  公开（公告）日：1990-01-31
• US4755511A
  申请人：——

  公开号：US4755511A

  公开（公告）日：1988-07-05
• Inotropic, vasodilator and low Km, cAMP-selective, cGMP-inhibited phosphodiesterase (PDE III) inhibitory activities of 4a-methyl-4,4a-dihydro-5H-indeno[1,2-c]pyridazin-3(2H)-ones and 4a-methyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-ones
  作者：SJ Bakewell、WJ Coates、MB Comer、ML Reeves、BH Warrington

  DOI：10.1016/0223-5234(90)90196-a

  日期：1990.11

  Novel 7-substituted-4,4a-dihydro-4a-methyl-5H-indenol[1,2-c]pyridazin-3[2H]-ones and 8-substituted-4a-methylbenzo[h]cinnolin-3[2H]-ones have been synthesized and their PDE III inhibitory, inotropic and vasodilator potencies compared with those of their normethyl analogues and their bicyclic 4,5-dihydro-6-phenylpyridazinone analogues. The structure-activity relationships of the tricyclic pyridazinones differ from those of bicyclic pyridazinones mainly in respect of the effect of introducing the methyl group into the pyridazinone ring. Whilst in the 4,5-dihydro-6-phenylpyridazin-3(2H)-ones, introduction of a 5-methyl group has been widely reported to lead to compounds of significantly greater potency, the novel tricyclic 4a-methylpyridazinones showed similar levels of inotropic, vasodilator and PDE III inhibitory potency to their normethyl analogues. Possible reasons for this difference in behaviour are discussed.