1-(3,4-dichlorophenyl)pyrazolidin-3-one | 6119-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dichlorophenyl)pyrazolidin-3-one
• 英文别名: 1-(3,4-Dichlorophenyl)-3-pyrazolidinone
• CAS: 6119-14-8
• 化学式: C₉H₈Cl₂N₂O
• 分子量: 231.081
• InChiKey: IOSBJPUWTOXWKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3,4-dichlorophenyl)pyrazolidin-3-one 在 氢氧化钾 作用下， 以 水 为溶剂， 生成 1-(3,4-dichlorophenyl)-1H-pyrazol-3-ol
  参考文献：
  名称：

  Method for producing N-substituted 3-hydroxypyrazoles

  摘要：

  描述了一种制备公式I中N-取代的3-羟基吡唑的过程，其中R1是未取代或取代的烷基，烯基，炔基，环烷基，芳基或杂环芳基，R2，R3是氢，氰，卤素，未取代或取代的烷基，烯基，炔基，环烷基，芳基或杂环芳基，通过氧化相应的吡唑啉-3-酮实现。

  公开号：

  US06040458A1

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.
• VERFAHREN ZUR HERSTELLUNG VON N-SUBSTITUIERTEN 3-HYDROXYPYRAZOLEN
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0946514B1

  公开（公告）日：2003-05-02
• US6040458A
  申请人：——

  公开号：US6040458A

  公开（公告）日：2000-03-21
• Method for producing N-substituted 3-hydroxypyrazoles
  申请人：BASF Aktiengesellschaft

  公开号：US06040458A1

  公开（公告）日：2000-03-21

  A process is described for preparing N-substituted 3-hydroxypyrazoles of the formula I ##STR1## where R.sup.1 is unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl and R.sup.2, R.sup.3 are hydrogen, cyano, halogen and unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl, by oxidizing a corresponding pyrazolidin-3-one.

  描述了一种制备公式I中N-取代的3-羟基吡唑的过程，其中R1是未取代或取代的烷基，烯基，炔基，环烷基，芳基或杂环芳基，R2，R3是氢，氰，卤素，未取代或取代的烷基，烯基，炔基，环烷基，芳基或杂环芳基，通过氧化相应的吡唑啉-3-酮实现。