7-acetamido-4a-dihydro-4a-methyl-5H-indeno<1,2-c>pyridazin-3(2H)-one | 103422-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 7-acetamido-4a-dihydro-4a-methyl-5H-indeno<1,2-c>pyridazin-3(2H)-one
• 英文别名: 7-(acetylamino)-4,4a-dihydro-5H-indeno<1,2-c>pyridazin-3-one；7-acetamido-4,4a-dihydro-[5H]-indeno[1,2-c]pyridazin-3[2H]-one；N-(3,4,4a,5-Tetrahydro-3-oxo-2H-indeno(1,2-c)pyridazin-7-yl)acetamide；N-(3-oxo-2,4,4a,5-tetrahydroindeno[1,2-c]pyridazin-7-yl)acetamide
• CAS: 103422-54-4；103602-96-6；103602-98-8
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: VZQRLYZMJFIJOU-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: tetrahydrofuran (109-99-9))
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-acetamido-4a-dihydro-4a-methyl-5H-indeno<1,2-c>pyridazin-3(2H)-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以33%的产率得到7-amino-4,4a-dihydro-5H-indeno<1,2-c>pyridazine-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：

  5-acetamido-2-dimethylaminomethyl-1-indanone hydrochloride 在 盐酸 、 硫酸 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 1.58h， 生成 7-acetamido-4a-dihydro-4a-methyl-5H-indeno<1,2-c>pyridazin-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

• Conformationally restricted congeners of hypotensive and platelet aggregation inhibitors: 6-aryl-5-methyl-4,5-dihydro-3(2H)-pyridazinones derived from 5H-indeno[1,2-c]pyridazine
  作者：Giorgio Cignarella、Daniela Barlocco、Gerard A. Pinna、Mario Loriga、Odoardo Tofanetti、Mauro Germini、Franca Sala

  DOI：10.1021/jm00161a010

  日期：1986.11

  A number of 7-amino and 7-acylamino substituted 4,4a-dihydro-5H-indeno[1,2-c]pyridazin-3-ones have been synthesized as rigid congeners of hypotensive 6-aryl-5-methyl-4,5-dihydro-3(2H)-pyridazinones and tested as antihypertensive, antithrombotic, antiulcer, and antiinflammatory agents. Unlike the previously described 7-cyano derivative, which displayed only antiinflammatory action, the new series exhibited

  已经合成了许多7-氨基和7-酰基氨基取代的4,4a-二氢-5H-茚并[1,2-c]哒嗪-3-酮作为降血压的6-芳基-5-甲基-4的刚性同类物， 5-二氢-3（2H）-哒嗪酮，经测试可作为降压药，抗血栓药，抗溃疡药和抗炎药。与先前描述的仅显示抗炎作用的7-氰基衍生物不同，新系列具有显着的抗高血压和抗血栓形成特性。在这方面，发现7-氨基（2b）和7-乙酰氨基（2c）衍生物在降低自发性高血压大鼠的血压和保护小鼠免于血栓形成方面是最有效和最持久的。这些化合物以及7-（2-氯丙酰基）衍生物2d也显示出抗炎活性。另外2c
• 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。
• Tricyclic dihydropyridazinones and pharmaceutical compositions contaning them
  申请人：BOEHRINGER MANNHEIM ITALIA S.P.A.

  公开号：EP0169443A2

  公开（公告）日：1986-01-29

  The tricyclic dihydropyridazinone derivatives having formula I are endowed with interesting hypotensive, vasodilating, antiaggregant, antithrombotic and cytoprotective properties and are therefore useful in human or veterinary medicine.

  三环二氢哒嗪酮衍生物具有式 I 的三环二氢哒嗪酮衍生物具有有趣的降血压、血管扩张、抗聚集、抗血栓和细胞保护特性，因此可用于人类或兽医领域。
• 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：——
• CIGNARELLA G.; BARLOCCO D.; PINNA G. A.; LORIGA M.; TOFANETTI O.; GERMINI+, J. MED. CHEM., 29,(1986) N 11, 2191-2194
  作者：CIGNARELLA G.、 BARLOCCO D.、 PINNA G. A.、 LORIGA M.、 TOFANETTI O.、 GERMINI+

  DOI：——

  日期：——