4,4-Dimethyl-5-(4-methylsulfanyl-phenyl)-2,4-dihydro-pyrazol-3-one | 108818-83-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4,4-Dimethyl-5-(4-methylsulfanyl-phenyl)-2,4-dihydro-pyrazol-3-one
• 英文别名: 4,4-dimethyl-3-(4-methylsulfanylphenyl)-1H-pyrazol-5-one
• CAS: 108818-83-3
• 化学式: C₁₂H₁₄N₂OS
• 分子量: 234.322
• InChiKey: ZMGUYMDYBPCHNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-Dimethyl-5-(4-methylsulfanyl-phenyl)-2,4-dihydro-pyrazol-3-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到2,4-dihydro-5-<4-(methylsulfinyl)phenyl>-4,4-dimethyl-3H-pyrazol-3-one
  参考文献：
  名称：

  Cardiotonic agents. 6. Synthesis and inotropic activity of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones: ring-contracted analogs of imazodan (CI-914)

  摘要：

  A series of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones was synthesized and evaluated for positive inotropic activity. Only compounds with two small alkyl groups at C-4 showed significant activity. The structure-activity relationships for optimal inotropic activity are presented and compared with those of the 4,5-dihydro-3(2H)-pyridazinone series. The phosphodiesterase inhibitory activity is also reported and correlated with the substitution pattern at C-4 in the pyrazolone ring.

  DOI：

  10.1021/jm00393a007
• 作为产物：
  描述：

  2,2-Dimethyl-3-(4-methylsulfanyl-phenyl)-3-oxo-propionic acid methyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以62%的产率得到4,4-Dimethyl-5-(4-methylsulfanyl-phenyl)-2,4-dihydro-pyrazol-3-one
  参考文献：
  名称：

  Cardiotonic agents. 6. Synthesis and inotropic activity of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones: ring-contracted analogs of imazodan (CI-914)

  摘要：

  A series of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones was synthesized and evaluated for positive inotropic activity. Only compounds with two small alkyl groups at C-4 showed significant activity. The structure-activity relationships for optimal inotropic activity are presented and compared with those of the 4,5-dihydro-3(2H)-pyridazinone series. The phosphodiesterase inhibitory activity is also reported and correlated with the substitution pattern at C-4 in the pyrazolone ring.

  DOI：

  10.1021/jm00393a007

文献信息

• SIRCAR, ILA;MORRISON, GLENN C.;BURKE, SANDRA E.;SKEEAN, RICHARD;WEISHAAR,+, J. MED. CHEM., 30,(1987) N 10, 1724-1728
  作者：SIRCAR, ILA、MORRISON, GLENN C.、BURKE, SANDRA E.、SKEEAN, RICHARD、WEISHAAR,+

  DOI：——

  日期：——
• Cardiotonic agents. 6. Synthesis and inotropic activity of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones: ring-contracted analogs of imazodan (CI-914)
  作者：Ila Sircar、Glenn C. Morrison、Sandra E. Burke、Richard Skeean、Ronald E. Weishaar

  DOI：10.1021/jm00393a007

  日期：1987.10

  A series of 2,4-dihydro-5-[4-(1H-imidazol-1-yl)phenyl]-3H-pyrazol-3-ones was synthesized and evaluated for positive inotropic activity. Only compounds with two small alkyl groups at C-4 showed significant activity. The structure-activity relationships for optimal inotropic activity are presented and compared with those of the 4,5-dihydro-3(2H)-pyridazinone series. The phosphodiesterase inhibitory activity is also reported and correlated with the substitution pattern at C-4 in the pyrazolone ring.