2-(4-fluorophenyl)-5-(piperidin-4-yl)-3-(pyridin-4-yl)-pyrrole | 188343-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(4-fluorophenyl)-5-(piperidin-4-yl)-3-(pyridin-4-yl)-pyrrole
• 英文别名: 2-(4-fluorophenyl)-5-(piperidin-4-yl)-3-(4-pyridinyl)-pyrrole；2-(4-fluorophenyl)-5-(piperidin-4-yl)-3-(4-pyridyl)-pyrrole；4-[2-(4-fluorophenyl)-5-piperidin-4-yl-1H-pyrrol-3-yl]pyridine
• CAS: 188343-78-4
• 化学式: C₂₀H₂₀FN₃
• 分子量: 321.397
• InChiKey: VTRDFQVZALPXRU-UHFFFAOYSA-N

物化性质

• 沸点：
  487.3±45.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-5-(piperidin-4-yl)-3-(pyridin-4-yl)-pyrrole 在 乙酸酐 作用下， 以 吡啶 为溶剂， 生成 2-(4-fluorophenyl)-5-(N-acetyl-piperidin-4-yl)-3-(pyridin-4-yl)-pyrrole
  参考文献：
  名称：

  2-substituted aryl pyrroles, compositions containing such compounds and

  摘要：

  本发明涉及2-取代芳基吡咯烷，以及含有这种化合物的组合物和治疗方法。细胞因子介导的疾病是指发生一种或多种细胞因子的过度或失调产生或活性的疾病或状况。白细胞介素-1（IL-1）、白细胞介素-6（IL-6）、白细胞介素-8（IL-8）和肿瘤坏死因子（TNF）是涉及的细胞因子。

  公开号：

  US05792778A1
• 作为产物：
  描述：

  benzyl 4-(5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-pyrrol-2-yl)piperidine-1-carboxylate 在 palladium on activated charcoal 氢气 作用下， 生成 2-(4-fluorophenyl)-5-(piperidin-4-yl)-3-(pyridin-4-yl)-pyrrole
  参考文献：
  名称：

  Synthesis and SAR of 2,3-diarylpyrrole inhibitors of parasite cGMP-dependent protein kinase as novel anticoccidial agents

  摘要：

  Several analogs of 2,3-diaryl pyrroles were synthesized and evaluated as inhibitors of Eimeria tenella cGMP-dependent protein kinase and in. in vivo anticoccidial assays. A 4-fluorophenyl group enhances both in vitro and in Vivo activities. The most potent analogs are the-5-(N-methyl, N-ethyl, and N-methylazetidine methyl) piperidyl derivatives 12, 23, and 34. These compounds have a broad spectrum of activity. Based on the in vivo efficacy and cost of synthesis, the N-ethyl analog 23 was chosen as a novel anticoccidial agent for a field trial. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.060

文献信息

• [EN] 2-SUBSTITUTED ARYL PYRROLES, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF USE<br/>[FR] PYRROLES D'ARYLE SUBSTITUES EN POSITION 2, COMPOSITIONS CONTENANT DE TELS COMPOSES ET LEURS MODES D'UTILISATION
  申请人：MERCK & CO., INC.

  公开号：WO1997005877A1

  公开（公告）日：1997-02-20

  (EN) The present invention addresses 2-substituted aryl pyrroles, as well as compositions containing such compounds and methods of treatment. Cytokine mediated diseases refers to diseases or conditions in which excessive or unregulated production or activity of one or more cytokines occurs. Interleukin-1 (IL-1), Interleukin-6 (IL-6), Interleukin-8 (IL-8) and Tumor Necrosis Factor (TNF) are cytokines which are involved.(FR) L'invention se rapporte à des pyrroles d'aryle substitués en position 2, ainsi qu'à des compositions contenant de tels composés et à leurs modes d'utilisation. Les maladies induites par les cytokines sont des maladies ou des pathologies dans lesquelles intervient la production ou l'activité excessive ou non contrôlée d'une ou de plusieurs cytokines. L'interleukine-1 (IL-1), l'interleukine-6 (IL-6), l'interleukine-8 (IL-8) et le facteur de nécrose tumorale (TNF) figurent parmi les cytokines impliquées.

  (中) 本发明涉及2-取代芳基吡咯，以及含有该类化合物的组合物和治疗方法。细胞因子介导的疾病是指一种或多种细胞因子的过度或不受控制的产生或活性在其中发生的疾病或状况。介白素-1（IL-1）、介白素-6（IL-6）、介白素-8（IL-8）和肿瘤坏死因子（TNF）是涉及的细胞因子。
• Diaryl piperidyl pyrrole derivatives as antiprotozoal agents
  申请人：Merck & Co., Inc.

  公开号：US06291480B1

  公开（公告）日：2001-09-18

  Trisubstituted pyrroles are antiprotozoal agents useful in the treatment and prevention of protozoal diseases in human and animals, including the control of coccidiosis in poultry.

  三取代吡咯是抗原虫药物，可用于治疗和预防人类和动物的原虫病，包括控制家禽球虫病。
• Anticoccidial compounds
  申请人：Merck & Co., Inc.

  公开号：US06384052B1

  公开（公告）日：2002-05-07

  Trisubstituted pyrroles are useful in the control of coccidiosis in poultry.

  三取代吡咯在家禽球虫病的控制中很有用。
• Hydroxylated N-alkyl-4-piperidinyl-2,3-diarylpyrrole derivatives as potent broad-spectrum anticoccidial agents
  作者：Gui-Bai Liang、Xiaoxia Qian、Tesfaye Biftu、Dennis Feng、Michael Fisher、Tami Crumley、Sandra J. Darkin-Rattray、Paula M. Dulski、Anne Gurnett、Penny Sue Leavitt、Paul A. Liberator、Andrew S. Misura、Samantha Samaras、Tamas Tamas、Dennis M. Schmatz、Matthew Wyvratt

  DOI：10.1016/j.bmcl.2005.06.096

  日期：2005.10

  Diaryl-(4-piperidinyl)-pyrrole derivatives bearing hydroxylated N-alkyl substituents have been synthesized and evaluated as anticoccidial agents. High potency in Et-PKG inhibition and broad-spectrum anticoccidial activities have been observed on compounds, such as 4b and 5h, which are fully efficacious in vivo at 50 ppm in feed. (c) 2005 Elsevier Ltd. All rights reserved.
• N-Alkyl-4-piperidinyl-2,3-diarylpyrrole derivatives with heterocyclic substitutions as potent and broad spectrum anticoccidial agents
  作者：Gui-Bai Liang、Xiaoxia Qian、Dennis Feng、Michael Fisher、Tami Crumley、Sandra J. Darkin-Rattray、Paula M. Dulski、Anne Gurnett、Penny Sue Leavitt、Paul A. Liberator、Andrew S. Misura、Samantha Samaras、Tamas Tamas、Dennis M. Schmatz、Matthew Wyvratt、Tesfaye Biftu

  DOI：10.1016/j.bmcl.2008.01.104

  日期：2008.3

  Diaryl-(4-piperidinyl)-pyrrole derivatives bearing cyclic amine substituents have been synthesized and evaluated as anti-coccidial agents. Improvements in potency of Et-PKG inhibition, such as azetidine derivative 3a, and broad spectrum anticoccidial activities in feed, such as morpholine derivative 8c, have been achieved. (C) 2008 Elsevier Ltd. All rights reserved.