7-benzyl-N-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1H-1,5-naphthyridine-3-carboxamide | 675614-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-benzyl-N-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1H-1,5-naphthyridine-3-carboxamide
• CAS: 675614-22-9
• 化学式: C₂₃H₁₈FN₃O₃
• 分子量: 403.413
• InChiKey: HTJZULVCICQELB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  91.3
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 3-amino-5-(phenylmethyl)-2-pyridinecarboxylate 在 sodium ethanolate 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 生成 7-benzyl-N-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1H-1,5-naphthyridine-3-carboxamide
  参考文献：
  名称：

  Combining symmetry elements results in potent naphthyridinone (NTD) HIV-1 integrase inhibitors

  摘要：

  A series of naphthyridinone HIV-1 integrase strand-transfer inhibitors have been designed based on a psdeudo-C2 symmetry element present in the two-metal chelation pharmacophore. A combination of two distinct inhibitor binding modes resulted in potent inhibition of the integrase strand-transfer reaction in the low nM range. Effects of aryl and N1 substitutions are disclosed including the impact on protein binding adjusted antiviral activity. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.08.082

文献信息

• Heterocyclic compounds having inhibitory activity against HIV integrase
  申请人：Murai Hitoshi

  公开号：US20090118233A1

  公开（公告）日：2009-05-07

  A heterocyclic compound of the formula (I): wherein B 1 is —C(R 2 )═ or —N═; R 1′ is H, etc.; one of R 1 and R 2 is -Z 1 -Z 2 -Z 3 -R 5 wherein Z 1 and Z 3 are independently single bond, optionally substituted alkylene, etc.; Z 2 is single bond, optionally substituted alkylene, etc.; R 5 is optionally substituted aryl, optionally substituted heteroaryl, etc., and the other of R 1 and R 2 is H; -A 1 - is —C(—Y)═C(—R A )—C(—R 3 )═C(—R 4 )—, etc. wherein Y is OH, etc.; R A is —COR 7 wherein R 7 is OH, etc.; one of R 3 and R 4 is carboxy, etc., and the other of R 1 and R 2 is H, etc, a prodrug thereof, a pharmaceutically acceptable salt thereof, and a solvate thereof, having an antiviral activity, more particularly, an inhibitory activity against HIV integrase, and a pharmaceutical composition containing the same, especially an anti-HIV drug.

  一种具有以下式（I）的杂环化合物：其中B1为—C（R2）═或—N═；R1'为H等；R1和R2中的一个为-Z1-Z2-Z3-R5，其中Z1和Z3分别为单键，可选择性地取代的烷基等；Z2为单键，可选择性地取代的烷基等；R5为可选择性取代的芳基，可选择性取代的杂环芳基等；R1和R2中的另一个为H；-A1-为—C（—Y）═C（—RA）—C（—R3）═C（—R4）—等，其中Y为OH等；RA为—COR7，其中R7为OH等；R3和R4中的一个为羧基等，另一个为H等。该化合物的前药、其药学上可接受的盐和溶剂化物具有抗病毒活性，尤其是对HIV整合酶的抑制活性，并且包含该化合物的药物组合物，特别是一种抗HIV药物。
• US7358249B2
  申请人：——

  公开号：US7358249B2

  公开（公告）日：2008-04-15
• Combining symmetry elements results in potent naphthyridinone (NTD) HIV-1 integrase inhibitors
  作者：Brian A. Johns、Takashi Kawasuji、Jason G. Weatherhead、Eric E. Boros、James B. Thompson、Edward P. Garvey、Scott A. Foster、Jerry L. Jeffrey、Wayne H. Miller、Noriyuki Kurose、Kenichi Matsumura、Tamio Fujiwara

  DOI：10.1016/j.bmcl.2011.08.082

  日期：2011.11

  A series of naphthyridinone HIV-1 integrase strand-transfer inhibitors have been designed based on a psdeudo-C2 symmetry element present in the two-metal chelation pharmacophore. A combination of two distinct inhibitor binding modes resulted in potent inhibition of the integrase strand-transfer reaction in the low nM range. Effects of aryl and N1 substitutions are disclosed including the impact on protein binding adjusted antiviral activity. (C) 2011 Published by Elsevier Ltd.