1-Phenyl-4-(pyridin-2-ylsulfanyl)-pyrazolidin-3-one | 133043-62-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-Phenyl-4-(pyridin-2-ylsulfanyl)-pyrazolidin-3-one
• 英文别名: 1-phenyl-4-pyridin-2-ylsulfanylpyrazolidin-3-one
• CAS: 133043-62-6
• 化学式: C₁₄H₁₃N₃OS
• 分子量: 271.343
• InChiKey: CXAJQEZNTDRWNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  菲尼酮 以37%的产率得到
  参考文献：
  名称：

  HLASTA, DENNIS J.;CASEY, FRANCIS B.;FERGUSON, EDWARD W.;GANGELL, SALLY J.+, J. MED. CHEM., 34,(1991) N, C. 1560-1570

  摘要：

  DOI：

文献信息

• 5-Lipoxygenase inhibitors: the synthesis and structure-activity relationships of a series of 1-phenyl-3-pyrazolidinones
  作者：Dennis J. Hlasta、Francis B. Casey、Edward W. Ferguson、Sally J. Gangell、Martha R. Heimann、Edward P. Jaeger、Rudolph K. Kullnig、Robert J. Gordon

  DOI：10.1021/jm00109a006

  日期：1991.5

  A series of analogues of the 5-lipoxygenase inhibitor 1-phenyl-3-pyrazolidinone (phenidone, 1a) has been prepared via two complementary new synthetic methods. The reaction of various electrophiles with the dianion of 1a or with an N-silylpyrazolidinone anion gave the desired 4-substituted pyrazolidinones (Scheme I and II). A new procedure was developed for the resolution of 4-substituted pyrazolidinones (Scheme V). A regression study on 21 compounds in this series showed a correlation of increased inhibitor potency (pIC50) with increased compound lipophilicity (log P) and with an N-phenyl electronic effect as measured by the C-13 NMR chemical shift parameter CNMR1' (R2 = 0.79). The most potent 5-lipoxygenase inhibitor in this series was 4-(ethylthio)-1-phenyl-3-pyrazolidinone (1n) with an IC50 of 60 nM. Another member of this series, 4-(2-methoxyethyl)-1-phenyl-3-pyrazolidinone (1f, IC50 = 0-48-mu-M), although less potent than 1n, was better tolerated in the whole animal relative to phenidone (1a) and also displayed good oral activity in two models of 5-lipoxygenase inhibition. On the basis of a structure-activity relationship study, a mechanism for the inhibition of 5-lipoxygenase by this class of inhibitors was proposed.
• HLASTA, DENNIS J.;CASEY, FRANCIS B.;FERGUSON, EDWARD W.;GANGELL, SALLY J.+, J. MED. CHEM., 34,(1991) N, C. 1560-1570
  作者：HLASTA, DENNIS J.、CASEY, FRANCIS B.、FERGUSON, EDWARD W.、GANGELL, SALLY J.+

  DOI：——

  日期：——