8-methoxy-4,4a,5,6-tetrahydrobenzocinnolin-3(2H)-one | 52240-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 8-methoxy-4,4a,5,6-tetrahydrobenzocinnolin-3(2H)-one
• 英文别名: 8-Methoxy-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one；8-methoxy-4,4a,5,6-tetrahydro-2H-benzo[h]cinnolin-3-one；4,4a,5,6-tetra-hydro-8-methoxybenzo[h]cinnolin-3[2H]-one；8-methoxy-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3[2H]-one；8-methoxy-4,4a,5,6-tetrahydro-2H-benzo[h]cinnolin-3-one
• CAS: 52240-33-2
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: UZLLDIQAODKZOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methoxy-4,4a,5,6-tetrahydrobenzocinnolin-3(2H)-one 在 sodium nitrobenzenesulfonate 作用下， 以95%的产率得到8-methoxy-5,6-dihydrobenzocinnolin-3(2H)-one
  参考文献：
  名称：

  一系列新的苯并[h] cinnolinone衍生物的合成和醛糖还原酶抑制活性。

  摘要：

  继我们先前对哒嗪酮羧酸作为有效和选择性醛糖还原酶（ALR2）抑制剂的研究之后，一系列新的苯并[h]肉桂醇酮羧酸系列分别在4、7-10位取代，并且在中心环和合成并测试了酸性侧链上的A1作为ALR2的抑制剂。与先前合成的化合物进行比较可以使我们为此类化合物更精确地定义构效关系。实际上，除了酸性侧链的重要性外，它们的性质还受到苯并[h]肉桂醇核上存在的取代基的强烈影响，其效力范围从索比尼尔到非常弱的活性化合物。

  DOI：

  10.1016/s0014-827x(00)00035-5
• 作为产物：
  描述：

  2-dimethylaminomethyl-6-methoxy-3,4-dihydronaphthalen-1(2H)-one hydrochloride 在 盐酸 、 一水合肼 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 7.83h， 生成 8-methoxy-4,4a,5,6-tetrahydrobenzocinnolin-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

文献信息

• Efficient Aromatization of 4,5-Dihydro-3(2<i>H</i>)-Pyridazinones Substituted at 5 Position by Using Anhydrous Copper (II) Chloride
  作者：Eddy Sotelo、Enrique Raviña

  DOI：10.1080/00397910008087285

  日期：2000.1

  An efficient conversion of 5-substituted-4,5-dihydro-3(2H)-pyridazinones into their corresponding dehydrogenated derivatives was achieved by treatment with anhydrous copper(II) chloride in acetonitrile.
• Ravina; Fueyo; Teran, Pharmazie, 1992, vol. 47, # 8, p. 574 - 577
  作者：Ravina、Fueyo、Teran、Cid、Garcia Mera、Orallo、Bardan

  DOI：——

  日期：——
• 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：——
• GARCIA, MERA, G.;RAVINA, E.;SANTANA, L.;ORALLO, F.;FONTENLA, J. A.;CALLEJ+, AN. QUIM. PUBL. REAL. SOC. ESP. QUIM., 1985, 81, N 3, 280-283
  作者：GARCIA, MERA, G.、RAVINA, E.、SANTANA, L.、ORALLO, F.、FONTENLA, J. A.、CALLEJ+

  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