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6-(3-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one | 36725-31-2

中文名称
——
中文别名
——
英文名称
6-(3-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one
英文别名
6-(3-amino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one;6-(m-Anilino)-4,5-dihydro-5-methyl-3(2H)-pyridazinon;3-(3-aminophenyl)-4-methyl-4,5-dihydro-1H-pyridazin-6-one
6-(3-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one化学式
CAS
36725-31-2
化学式
C11H13N3O
mdl
——
分子量
203.244
InChiKey
SNHLRYZWIWHWFX-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 密度:
    1.30±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    0.8
  • 重原子数:
    15
  • 可旋转键数:
    1
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.27
  • 拓扑面积:
    67.5
  • 氢给体数:
    2
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Pyridazinyl phenyl hydrazones useful against congestive heart failure
    摘要:
    公式(I)中的治疗活性化合物,其中R1到R4表示氢、烷基、烯基、芳基、芳基烷基、羧基烷基、羟基烷基或卤代烷基,或者R2和R3形成一个由5-7个碳原子组成的环。R5到R9表示氢、烷基、烯基、芳基、芳基烷基、酰基、羟基、烷氧基、烷氧羰基、氨基、酰胺基、烷基胺基、芳氧基、卤素、氰基、硝基、羧基、烷基磺酰基、磺酰胺基或三氟甲基,其中上述每个芳基残基本身或作为另一群的一部分可能被取代,并且其药物学上可接受的盐和酯。这些化合物增加心肌收缩蛋白的钙敏感性,因此在充血性心力衰竭的治疗中非常有用。
    公开号:
    US20030158200A1
  • 作为产物:
    描述:
    2-溴-1-(3-硝基苯基)丙烷-1-酮盐酸铁粉 、 sodium hydride 、 一水合肼 作用下, 以 乙醇N,N-二甲基甲酰胺 为溶剂, 反应 12.0h, 生成 6-(3-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one
    参考文献:
    名称:
    Synthesis and Structure−Activity Relationships of cis-Tetrahydrophthalazinone/Pyridazinone Hybrids:  A Novel Series of Potent Dual PDE3/PDE4 Inhibitory Agents
    摘要:
    In this study, the synthesis and in vitro and in vivo pharmacological investigations of a new series of phthalazinone/pyridazinone hybrids with both PDE3 and PDE4 inhibitory activities are described. These compounds combine the pharmacophores of recently discovered 4a,5,8,8a-tetrahydro-2H-phthalazin-1-one-type inhibitors of PDE4 and the well-known 2H-pyridazin-3-one-type PDE3 inhibitors such as the tetrahydrobenzimidazoles. Most of the synthesized compounds are pharmacologically spoken PDE3/PDE4 hybrids. All hybrids show potent PDE4 inhibitory activity (pIC(50) = 7.0-8.7), whereas the pIC(50) values for inhibition of PDE3 vary from 5.4 to 7.5. In general, analogues with a 5-methyl-4,5-dihydropyridazinone moiety exhibit the highest PDE3 inhibitory activities. The highest in vivo antiinflammatory activity is displayed by phthalazinones 43 and 44 showing, at a dose of 30 mumol/kg po, 46% inhibition of arachidonic acid (AA) induced mouse ear edema. No correlation was found between the in vitro PDE3 and/or PDE4 inhibitory activity and the in vivo antiinflammatory capacity after oral dosing.
    DOI:
    10.1021/jm030776l
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文献信息

  • PYRIDAZINYL PHENYL HYDRAZONES USEFUL AGAINST CONGESTIVE HEART FAILURE
    申请人:Orion Corporation
    公开号:EP1265871B1
    公开(公告)日:2006-02-08
  • US6699868B2
    申请人:——
    公开号:US6699868B2
    公开(公告)日:2004-03-02
  • [EN] PYRIDAZINYL PHENYL HYDRAZONES USEFUL AGAINST CONGESTIVE HEART FAILURE<br/>[FR] PYRIDAZINYL PHENYL HYDRAZONES UTILES CONTRE L'INSUFFISANCE CARDIAQUE CONGESTIVE
    申请人:ORION CORP
    公开号:WO2001068611A1
    公开(公告)日:2001-09-20
    Therapeutically active compounds of formula (I) in which R1 to R4 means hydrogen, alkyl, alkenyl, aryl, arylalkyl, carboxyalkyl, hydroxyalkyl or halogenalkyl, or R2 and R3 form a ring of 5-7 carbon atoms, R5 to R9 means hydrogen, alkyl, alkenyl, aryl, arylalkyl, acyl, hydroxy, alkoxy, alkoxycarbonyl, amino, acylamino, alkylamino, aryloxy, halogen, cyano, nitro, carboxy, alkylsulfonyl, sulfonamido or trifluoromethyl, wherein each aryl residue defined above by itself or as a part of another group may be substituted, and pharmaceutically acceptable salts and esters thereof. The compounds increase the calcium sensitivity of contractile proteins of the cardiac muscle and are thus useful in the treatment of congestive heart failure.
  • Synthesis and Structure−Activity Relationships of <i>cis</i>-Tetrahydrophthalazinone/Pyridazinone Hybrids:  A Novel Series of Potent Dual PDE3/PDE4 Inhibitory Agents
    作者:Margaretha Van der Mey、Kirsten M. Bommelé、Hildegard Boss、Armin Hatzelmann、Mike Van Slingerland、Geert J. Sterk、Hendrik Timmerman
    DOI:10.1021/jm030776l
    日期:2003.5.1
    In this study, the synthesis and in vitro and in vivo pharmacological investigations of a new series of phthalazinone/pyridazinone hybrids with both PDE3 and PDE4 inhibitory activities are described. These compounds combine the pharmacophores of recently discovered 4a,5,8,8a-tetrahydro-2H-phthalazin-1-one-type inhibitors of PDE4 and the well-known 2H-pyridazin-3-one-type PDE3 inhibitors such as the tetrahydrobenzimidazoles. Most of the synthesized compounds are pharmacologically spoken PDE3/PDE4 hybrids. All hybrids show potent PDE4 inhibitory activity (pIC(50) = 7.0-8.7), whereas the pIC(50) values for inhibition of PDE3 vary from 5.4 to 7.5. In general, analogues with a 5-methyl-4,5-dihydropyridazinone moiety exhibit the highest PDE3 inhibitory activities. The highest in vivo antiinflammatory activity is displayed by phthalazinones 43 and 44 showing, at a dose of 30 mumol/kg po, 46% inhibition of arachidonic acid (AA) induced mouse ear edema. No correlation was found between the in vitro PDE3 and/or PDE4 inhibitory activity and the in vivo antiinflammatory capacity after oral dosing.
  • Pyridazinyl phenyl hydrazones useful against congestive heart failure
    申请人:——
    公开号:US20030158200A1
    公开(公告)日:2003-08-21
    Therapeutically active compounds of formula (I) in which R 1 to R 4 means hydrogen, alkyl, alkenyl, aryl, arylalkyl, carboxyalkyl, hydroxyalkyl or halogenalkyl, or R 2 and R 3 form a ring of 5-7 carbon atoms. R 5 to R 9 means hydrogen, alkyl, alkenyl, aryl, arylalkyl, acyl, hydroxy, alkoxy, alkoxycarbonyl, amino, acylamino, alkylamino, aryloxy, halogen, cyano, nitro, carboxy, alkylsulfonyl, sulfonamido or trifluoromethyl, wherein each aryl residue defined above by itself or as a part of another group may be substituted, and pharmaceutically acceptable salts and esters thereof. The compounds increase the calcium sensitivity of contractile proteins of the cardiac muscle and are thus useful in the treatment of congestive heart failure.
    公式(I)中的治疗活性化合物,其中R1到R4表示氢、烷基、烯基、芳基、芳基烷基、羧基烷基、羟基烷基或卤代烷基,或者R2和R3形成一个由5-7个碳原子组成的环。R5到R9表示氢、烷基、烯基、芳基、芳基烷基、酰基、羟基、烷氧基、烷氧羰基、氨基、酰胺基、烷基胺基、芳氧基、卤素、氰基、硝基、羧基、烷基磺酰基、磺酰胺基或三氟甲基,其中上述每个芳基残基本身或作为另一群的一部分可能被取代,并且其药物学上可接受的盐和酯。这些化合物增加心肌收缩蛋白的钙敏感性,因此在充血性心力衰竭的治疗中非常有用。
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