2-[2-(4-fluorophenyl)acetyl]pyrazolidine-1-carboxylic acid benzyl ester | 745018-19-3

• 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: 2-[2-(4-fluorophenyl)acetyl]pyrazolidine-1-carboxylic acid benzyl ester
• 英文别名: Benzyl 2-[2-(4-fluorophenyl)acetyl]pyrazolidine-1-carboxylate；benzyl 2-[2-(4-fluorophenyl)acetyl]pyrazolidine-1-carboxylate
• CAS: 745018-19-3
• 化学式: C₁₉H₁₉FN₂O₃
• 分子量: 342.37
• InChiKey: JGVUPOZPINFXFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(4-fluorophenyl)acetyl]pyrazolidine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal Oxone 、 sodium hydroxide 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 2-(4-fluorophenyl)-3-(2-methanesulfonyl-pyrimidin-4-yl)-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one
  参考文献：
  名称：

  Development of Orally Bioavailable Bicyclic Pyrazolones as Inhibitors of Tumor Necrosis Factor-α Production

  摘要：

  2-Aryl-3-pyrimidinyl based tumor necrosis factor-alpha (TNF-alpha) inhibitors, which contain a novel bicyclic pyrazolope core, are described. Many showed low-nanomolar activity against lipopolysaccharide-induced TNF-alpha production in monocytic cells. Secondary screening data are presented for the pyrimidinyl bicyclic pyrazolones. Several of these analogues showed good oral bioavailability in rat and efficacy in the rat iodoacetate in vivo model.

  DOI：

  10.1021/jm049968m
• 作为产物：
  描述：

  pyrazolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 2-[2-(4-fluorophenyl)acetyl]pyrazolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Convergent synthesis of 2,3-bisarylpyrazolones through cyclization of bisacylated pyrazolidines and hydrazines

  摘要：

  Cyclization of various bisacylated hydrazines and pyrazolidines using DBU or sodium hydride leads to the formation of various mono-, bi- and tricyclic pyrazolone scaffolds in 41-98% yield. The convergent nature by which the precyclization intermediates are constructed allows for rapid derivatization about the pyrazolone core. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.063

文献信息

• Development of Orally Bioavailable Bicyclic Pyrazolones as Inhibitors of Tumor Necrosis Factor-α Production
  作者：Michael P. Clark、Steven K. Laughlin、Matthew J. Laufersweiler、Roger G. Bookland、Todd A. Brugel、Adam Golebiowski、Mark P. Sabat、Jennifer A. Townes、John C. VanRens、Jane F. Djung、Michael G. Natchus、Biswanath De、Lily C. Hsieh、Susan C. Xu、Rick L. Walter、Marlene J. Mekel、Sandra A. Heitmeyer、Kimberly K. Brown、Karen Juergens、Yetunde O. Taiwo、Michael J. Janusz

  DOI：10.1021/jm049968m

  日期：2004.5.1

  2-Aryl-3-pyrimidinyl based tumor necrosis factor-alpha (TNF-alpha) inhibitors, which contain a novel bicyclic pyrazolope core, are described. Many showed low-nanomolar activity against lipopolysaccharide-induced TNF-alpha production in monocytic cells. Secondary screening data are presented for the pyrimidinyl bicyclic pyrazolones. Several of these analogues showed good oral bioavailability in rat and efficacy in the rat iodoacetate in vivo model.
• Convergent synthesis of 2,3-bisarylpyrazolones through cyclization of bisacylated pyrazolidines and hydrazines
  作者：Todd A. Brugel、Tomas Hudlicky、Michael P. Clark、Adam Golebiowski、Mark Sabat、Mary Ann A. Endoma、Vu Bui、David Adams、Matthew J. Laufersweiler、Jennifer A. Maier、Roger G. Bookland、Biswanath De

  DOI：10.1016/j.tetlet.2006.03.063

  日期：2006.5

  Cyclization of various bisacylated hydrazines and pyrazolidines using DBU or sodium hydride leads to the formation of various mono-, bi- and tricyclic pyrazolone scaffolds in 41-98% yield. The convergent nature by which the precyclization intermediates are constructed allows for rapid derivatization about the pyrazolone core. (c) 2006 Elsevier Ltd. All rights reserved.