8-Methoxy-2,4,4a,5-tetrahydrochromeno[4,3-c]pyridazin-3-one | 133414-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-Methoxy-2,4,4a,5-tetrahydrochromeno[4,3-c]pyridazin-3-one
• CAS: 133414-50-3
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: OBUPGOBVHNUSAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-Methoxy-2,4,4a,5-tetrahydrochromeno[4,3-c]pyridazin-3-one 在 sodium hydroxide 、 sodium 3-nitrobenzenesulfonate 作用下， 以 水 为溶剂， 反应 1.0h， 以45%的产率得到10-Hydroxy-7-methoxy-3H,10H-9-oxa-3,4-diaza-phenanthren-2-one
  参考文献：
  名称：

  氧化剂钠意外行为米-nitrobenzenesulfonate：一类新的5-羟基的合成†苯并吡喃并[4,3- c ^ ]哒嗪-3（2 H ^） -酮

  摘要：

  钠米-硝基苯磺酸酯，广泛用于4,5-二氢-3-（2-脱氢ħ） -哒嗪酮为它们相应的芳族衍生物，以意想不到的方式的行为时-4,4a-二氢5 ħ [1]苯并吡喃并[4 ，3 - c ]哒嗪-3（2 H）-1被用作底物。描述了新型的5-羟基[1]苯并吡喃并[4,3 - c ]哒嗪-3（2 H）-ones的合成。

  DOI：

  10.1002/jhet.5570320114
• 作为产物：
  描述：

  3,4-二氢-7-甲氧基-4-氧代-2H-1-苯并吡喃-3-乙酸 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以68%的产率得到8-Methoxy-2,4,4a,5-tetrahydrochromeno[4,3-c]pyridazin-3-one
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 4,4a-dihydro-5H-[1]benzopyrano[4,3-c]pyridazin-3(2H)-ones bioisosters of antihypertensive and antithrombotic benzo[h]cinnolinones

  摘要：

  A series of 4,4a-dihydro-5H-[1]benzopyrano[4,3-c]pyridazin-3-(2H)-ones (2a-h), have been prepared and evaluated for their pharmacological profile as antihypertensive and antithrombotic agents. Compounds 2 were ineffective in lowering the blood pressure of spontaneously hypertensive rats (SHR), only 2c (R1 = NHCOCH3) showing a short lasting action (< 2 h). Compounds 2c and 2b (R1 = NH2) were found to be very active as antithrombotic agents in mice, being more potent than acetylsalicylic acid (ASA) taken as reference drug. Moreover, many derivatives of this class protected rats from formation of ASA or phenylbutazone (PBZ) induced ulcers, the most active being 2f (R2 = OCH3) (ED50 = 12.2 mg/kg and 25.4 mg/kg po in ASA and PBZ models, respectively).

  DOI：

  10.1016/0223-5234(90)90194-8

文献信息

• CIGNARELLA, G.;BARLOCCO, D.;CURZU, M. M.;PINNA, G. A.;CAZZULANI, P.;CASSI+, EUR. J. MED. CHEM., 25,(1990) N, C. 749-756
  作者：CIGNARELLA, G.、BARLOCCO, D.、CURZU, M. M.、PINNA, G. A.、CAZZULANI, P.、CASSI+

  DOI：——

  日期：——
• Synthesis and pharmacological evaluation of 4,4a-dihydro-5H-[1]benzopyrano[4,3-c]pyridazin-3(2H)-ones bioisosters of antihypertensive and antithrombotic benzo[h]cinnolinones
  作者：G Cignarella、D Barlocco、MM Curzu、GA Pinna、P Cazzulani、M Cassin、B Lumachi

  DOI：10.1016/0223-5234(90)90194-8

  日期：1990.11

  A series of 4,4a-dihydro-5H-[1]benzopyrano[4,3-c]pyridazin-3-(2H)-ones (2a-h), have been prepared and evaluated for their pharmacological profile as antihypertensive and antithrombotic agents. Compounds 2 were ineffective in lowering the blood pressure of spontaneously hypertensive rats (SHR), only 2c (R1 = NHCOCH3) showing a short lasting action (< 2 h). Compounds 2c and 2b (R1 = NH2) were found to be very active as antithrombotic agents in mice, being more potent than acetylsalicylic acid (ASA) taken as reference drug. Moreover, many derivatives of this class protected rats from formation of ASA or phenylbutazone (PBZ) induced ulcers, the most active being 2f (R2 = OCH3) (ED50 = 12.2 mg/kg and 25.4 mg/kg po in ASA and PBZ models, respectively).
• Unexpected behaviour of the oxidizing agent sodium<i>m</i>-nitrobenzenesulfonate: Synthesis of a new class of 5-hydroxy benzopyrano-[4,3-<i>c</i>]pyridazin-3(2<i>H</i>)-ones
  作者：Giorgio Cignarella、Daniela Barlocco

  DOI：10.1002/jhet.5570320114

  日期：1995.1

  m-nitrobenzene sulfonate, widely used in dehydrogenation of 4,5-dihydro-3(2H)-pyridazinones to their corresponding aromatic derivatives, behaves in an unexpected way when 4,4a-dihydro-5H[1]benzopyrano[4,3-c]pyridazin-3(2H)-ones are employed as substrate. The synthesis of a new class of 5-hydroxy[1]benzopyrano[4,3-c]pyridazin-3(2H)-ones is described.

  钠米-硝基苯磺酸酯，广泛用于4,5-二氢-3-（2-脱氢ħ） -哒嗪酮为它们相应的芳族衍生物，以意想不到的方式的行为时-4,4a-二氢5 ħ [1]苯并吡喃并[4 ，3 - c ]哒嗪-3（2 H）-1被用作底物。描述了新型的5-羟基[1]苯并吡喃并[4,3 - c ]哒嗪-3（2 H）-ones的合成。