4-oxo-4-<3,4-dihydro-3-oxo-1,4(2H)-benzoxazin-6-yl>butyric acid | 26518-86-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4-oxo-4-<3,4-dihydro-3-oxo-1,4(2H)-benzoxazin-6-yl>butyric acid
• 英文别名: γ-oxo-2H-1,4-benzoxazin-3(4H)-one-6-butanoic acid；6-βCarboxypropionyl-2H-1,4-benzoxazin-3-on；4-oxo-4-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-butyric acid；4-oxo-4-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)butanoic acid；4-oxo-4-(3-oxo-4H-1,4-benzoxazin-6-yl)butanoic acid
• CAS: 26518-86-5
• 化学式: C₁₂H₁₁NO₅
• mdl: MFCD02940785
• 分子量: 249.223
• InChiKey: GGVAABMOHZYRRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-oxo-4-<3,4-dihydro-3-oxo-1,4(2H)-benzoxazin-6-yl>butyric acid 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-Bromo-4-oxo-4-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-butyric acid methyl ester
  参考文献：
  名称：

  Reddy, G. Jagath; Rao, K. Srinivasa; Jayaveera, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 9, p. 2143 - 2146

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯酚 在 三氯化铝 、 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 4-oxo-4-<3,4-dihydro-3-oxo-1,4(2H)-benzoxazin-6-yl>butyric acid
  参考文献：
  名称：

  6-Benzoxazinylpyridazin-3-ones: potent, long-acting positive inotrope and peripheral vasodilator agents

  摘要：

  A series of 6-benzoxazinylpyridazin-3-ones was prepared and evaluated for inhibition of cardiac phosphodiesterase (PDE) fraction III in vitro and for positive inotropic activity in vivo. 6-[3,4-Dihydro-3-oxo-1,4(2H)-benzoxazin-7-yl]-2,3,4,5-tetrahydro-5 - methylpyridazin-3-one (bemoradan) was found to be an extremely potent and selective inhibitor of canine PDE fraction III and a long-acting, potent, orally active inotropic vasodilator agent in various canine models. Additional benzoxazin-6-yl and -8-yl compounds were also prepared. Altering the pyridazinone substitution from the 6-position to the 7-position produced a 14-fold increase in the iv cardiotonic potency (ED50) from 77 to 5.4 micrograms/kg while substitution at the 8-position reduced potency. Methyl substitution at various sites in the molecule was also examined. Positive inotropic activity was maintained for between 8 and 24 h after a single oral dose (100 micrograms/kg) of bemoradan in dogs, thus making it one of the most potent and long-acting orally effective inotropes yet described. Bemoradan is currently under development as a cardiotonic agent for use in the management of congestive heart failure.

  DOI：

  10.1021/jm00163a061

文献信息

• (+) and (-) enantiomers of 5-aliphatic-6-(benzoxazinyl- or benzothiazinyl)-2,3,4,5-tetrahydropyridazin-3-ones
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：EP0509845A1

  公开（公告）日：1992-10-21

  The present invention relates to (+) and (-) enantiomers of compounds of the formula: as further defined herein. The compounds are useful as cardiotonic and vasodilating agents and as inhibitors of phosphodiesterase fraction III and platelet aggregation. In addition, the compounds are active as smooth muscle relaxants and bronchodilators.

  本发明涉及式中化合物的(+)和(-)对映体： 的对映体。这些化合物可用作强心剂和血管扩张剂，以及磷酸二酯酶 III 部分和血小板聚集的抑制剂。此外，这些化合物还具有平滑肌松弛剂和支气管扩张剂的活性。
• Techer,H. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1970, vol. 270, p. 1601 - 1604
  作者：Techer,H. et al.

  DOI：——

  日期：——
• Reddy Sastry; Srinivasa Rao; Krishnan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 10, p. 882 - 884
  作者：Reddy Sastry、Srinivasa Rao、Krishnan、Rastogi、Jain、Verma、Tripathi、Singh、Seshagiri Rao、Kaushal

  DOI：——

  日期：——
• SASTRY, C. V. REDDY;RAO, K. SRINIVASA;KRISHNAN, V. S. H.;RASTOGI, K.;JAIN+, INDIAN J. CHEM. B, 28,(1989) N0, C. 882-884
  作者：SASTRY, C. V. REDDY、RAO, K. SRINIVASA、KRISHNAN, V. S. H.、RASTOGI, K.、JAIN+

  DOI：——

  日期：——
• COMBS, DONALD W.
  作者：COMBS, DONALD W.

  DOI：——

  日期：——