benzyl 4-(5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-pyrrol-2-yl)piperidine-1-carboxylate | 188343-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: benzyl 4-(5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-pyrrol-2-yl)piperidine-1-carboxylate
• 英文别名: MMV688509；2-(4-Fluorophenyl)-5-(1-benzyloxycarbonylpiperidin-4-yl)-3-(4-pyridinyl)pyrrole；benzyl 4-[5-(4-fluorophenyl)-4-pyridin-4-yl-1H-pyrrol-2-yl]piperidine-1-carboxylate
• CAS: 188343-76-2
• 化学式: C₂₈H₂₆FN₃O₂
• 分子量: 455.532
• InChiKey: PBVIXFOZRAMTSN-UHFFFAOYSA-N

物化性质

• 沸点：
  620.4±55.0 °C(Predicted)
• 密度：
  1.243±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(4-fluorophenyl)-5-(N-ethylpiperidin-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
• 作为产物：
  描述：

  4-(2-chloroacetyl)piperidine-1-carboxylic acid benzyl ester 在 ammonium acetate 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 2.58h， 生成 benzyl 4-(5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-pyrrol-2-yl)piperidine-1-carboxylate
  参考文献：
  名称：

  Chemical probes of a trisubstituted pyrrole to identify its protein target(s) in Plasmodium sporozoites

  摘要：

  Malaria is a disease that has a major impact in many developing nations, especially on the African continent. There is a need to develop new therapeutics and prophylactic treatments against it. A trisubstituted pyrrole was recently found to inhibit infection of mammalian hepatocytes by Plasmodium sporozoites, but the target of this agent is not known. In this study trisubstituted pyrrole derivatives with different substituents on a piperidinyl nitrogen were prepared. We determined if modifications of the piperidinyl nitrogen would accommodate a drug-biotin linking strategy for affinity purification of the trisubstituted pyrrole's target protein(s). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.010

文献信息

• Aliphatic amine substituted piperidyl diaryl pyrrole derivatives as antiprotozoal agents
  申请人：Merck & Co., Inc.

  公开号：US06432980B1

  公开（公告）日：2002-08-13

  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，包括控制家禽的球虫病。
• [EN] THERAPEUTIC METHODS AND COMPOUNDS<br/>[FR] PROCÉDÉS ET COMPOSÉS THÉRAPEUTIQUES
  申请人：UNIV RUTGERS

  公开号：WO2020219591A1

  公开（公告）日：2020-10-29

  The invention provides a compound of formula I: (I) or a pharmaceutically acceptable salt thereof, wherein R1-R5 Y have any of the values described in the specification, as well as compositions comprising a compound of formula I. The compounds are useful to treat malaria.

  该发明提供了一种化合物的公式I：(I)或其药用可接受的盐，其中R1-R5 Y具有规范中描述的任何值，以及包含公式I化合物的组合物。这些化合物可用于治疗疟疾。
• Aliphatic hydroxy substituted piperidyl diaryl pyrrole derivatives as antiprotozoal agents
  申请人：Merck & Co., Inc.

  公开号：US06528531B1

  公开（公告）日：2003-03-04

  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。
• 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，包括在家禽中控制球虫病。
• [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。