ethyl 3-amino-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate | 863442-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 3-amino-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate
• 英文别名: ethyl 3-amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate；Ethyl 3-amino-5-(4-fluorobenzyl)picolinate；ethyl 3-amino-5-[(4-fluorophenyl)methyl]pyridine-2-carboxylate
• CAS: 863442-92-6
• 化学式: C₁₅H₁₅FN₂O₂
• 分子量: 274.295
• InChiKey: KHNVQBBGUFUTMB-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  458.8±45.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate 在 三乙胺 、 O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 3-((2-(diethylamino)-2-oxoethyl)amino)-5-(4-fluorobenzyl)picolinate
  参考文献：
  名称：

  Naphthyridinone (NTD) integrase inhibitors 4. Investigating N1 acetamide substituent effects with C3 amide groups

  摘要：

  A series of N1 acetamide substituted naphthyridinone HIV-1 integrase inhibitors have been explored to understand structure-activity relationships (SAR) with various C3 amide groups. Investigations were evaluated using integrase enzyme inhibition, antiviral activity and protein binding effects to optimize the sub-structures. Lipophilicity was also incorporated to understand ligand lipophilic efficiency as a function of the structural modifications. Three representative analogs were further examined in a peripheral blood mononuclear cell (PBMC) antiviral assay as well as in vitro and in vivo drug metabolism and pharmacokinetic studies. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.011
• 作为产物：
  描述：

  2-(4-氟苄基)丙烯醛 在 二苯基膦叠氮化物 、 乙酸酐 、 对甲苯磺酸 、 三乙胺 、 sodium hydroxide 作用下， 生成 ethyl 3-amino-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate
  参考文献：
  名称：

  A Scaleable Synthesis of Methyl 3-Amino-5-(4-fluorobenzyl)-2-pyridinecarboxylate

  摘要：

  A scaleable synthesis of methyl 3-amino-5-(4-fiuorobenzy1)-2-pyridinecarboxylate (1b), starting from 5-bromo-2-methoxypyridine (8) and 4-fluorobenzaidehyde (9), is described. Key steps in the process include lithium-bromine exchange of 8, addition of the resulting lithiate to aldehyde 9, regioselective nitration of pyridone 12, and Pd-catalyzed alkoxycarbonylation of bromopyridine 15b. Overall yield of the five-stage synthesis was 23%; intermediates 10, 12, 13, 15b, and final product 1b center dot HCl were isolated as filterable solids. Compounds 1a,b are important intermediates in the synthesis of 7-benzylnaphthyridinones (e.g., 2) and related HIV-1 integrase inhibitors.

  DOI：

  10.1021/op7001326

文献信息

• HIV INTEGRASE INHIBITORS
  申请人：ViiV Healthcare Company

  公开号：US20150225399A1

  公开（公告）日：2015-08-13

  The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

  本发明具有作为HIV整合酶抑制剂的化合物，因此在抑制HIV复制、预防及/或治疗HIV感染以及治疗艾滋病及/或艾滋病相关综合症方面具有用途。
• Hiv Integrase Inhibitors
  申请人：Johns Alvin Brian

  公开号：US20070124152A1

  公开（公告）日：2007-05-31

  The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

  本发明涉及一种HIV整合酶抑制剂化合物，因此在抑制HIV复制，预防和/或治疗HIV感染以及治疗艾滋病和/或ARC方面具有用途。
• 2-oxonaphthyridine-3-carboxamides HIV integrase inhibitors
  申请人：Johns Brian Alvin

  公开号：US08691991B2

  公开（公告）日：2014-04-08

  The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

  本发明涉及能够抑制HIV整合酶的化合物，因此可用于抑制HIV复制，预防和/或治疗HIV感染，以及治疗艾滋病和/或ARC。
• WO2007/19100
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/19101
  申请人：——

  公开号：——

  公开（公告）日：——