ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate | 686266-21-7

• 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: ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate
• 英文别名: ethyl 4-hydroxy-2-oxo-1-phenylmethoxy-1,8-naphthyridine-3-carboxylate
• CAS: 686266-21-7
• 化学式: C₁₈H₁₆N₂O₅
• 分子量: 340.335
• InChiKey: CKYFJSIABXZWMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate 在 甲醇 、 sodium hydroxide 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (1-benzyloxy-2-oxo-1,8-naphthyridin-4-yl) trifluoromethanesulfonate
  参考文献：
  名称：

  WO2008/10964

  摘要：

  公开号：
• 作为产物：
  描述：

  ethyl 2-[(benzyloxy)amino]nicotinate 在 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.25h， 生成 ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate
  参考文献：
  名称：

  WO2008/10964

  摘要：

  公开号：

文献信息

• Anti-infective agents
  申请人：——

  公开号：US20040087577A1

  公开（公告）日：2004-05-06

  Compounds having the formula 1 are hepatitis C (HCV) polymerase inhibitors. Also disclosed are a composition and method for inhibiting hepatitis C (HCV) polymerase, processes for making the compounds, and synthetic intermediates employed in the processes.

  具有公式1的化合物是丙型肝炎（HCV）聚合酶抑制剂。还公开了一种用于抑制丙型肝炎（HCV）聚合酶的组成和方法，用于制造这些化合物的过程，以及在这些过程中使用的合成中间体。
• 1-HYDROXY NAPHTHYRIDINE COMPOUNDS AS ANTI-HIV AGENTS
  申请人：Williams Peter D.

  公开号：US20100056516A1

  公开（公告）日：2010-03-04

  1-Hydroxy naphthyridine compounds (e.g., 1-hydroxy naphthyridin-2(1H)-one compounds of Formula I are inhibitors of HIV integrase and/or HIV RNase H and inhibitors of HIV replication: (I) wherein X and R1-R6 are as defined herein. The compounds are useful in the prophylaxis and treatment of infection by HIV and in the prophylaxis, delay in the onset, and treatment of AIDS. The compounds are employed against HIV infection and AIDS as compounds per se or in the form of pharmaceutically acceptable salts. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other anti-HIV agents such as HIV antivirals, immunomodulators, antibiotics and vaccines.

  1-羟基萘啶化合物（例如，式I中的1-羟基萘啶-2（1H）-酮化合物）是HIV整合酶和/或HIV RNase H的抑制剂，也是HIV复制的抑制剂：（I）其中X和R1-R6如此定义。这些化合物对于预防和治疗HIV感染以及预防、延迟发病和治疗艾滋病非常有用。这些化合物可作为化合物本身或作为药学上可接受的盐的形式用于对抗HIV感染和艾滋病。这些化合物及其盐可作为制药组合物的成分，可以选择与其他抗HIV剂（例如HIV抗病毒药物，免疫调节剂，抗生素和疫苗）组合使用。
• Inhibitors of HCV NS5B polymerase: synthesis and structure–activity relationships of N-1-heteroalkyl-4-hydroxyquinolon-3-yl-benzothiadiazines
  作者：John K. Pratt、Pamela Donner、Keith F. McDaniel、Clarence J. Maring、Warren M. Kati、Hongmei Mo、Tim Middleton、Yaya Liu、Teresa Ng、Qinghua Xie、Rong Zhang、Debra Montgomery、Akhteruzzaman Molla、Dale J. Kempf、William Kohlbrenner

  DOI：10.1016/j.bmcl.2005.01.071

  日期：2005.3

  N-1-Alkylamino and N-1-alkyloxy-4-hydroxyquinolon-3-yl benzothiadiazines were synthesized and evaluated as inhibitors of genotype 1 HCV polymerase. The N-1-alkyloxy derivatives were not potent inhibitors, however N-1-alkylamino derivatives displayed comparable potency to carbon analogs. Analogs with aliphatic substituents were significantly more potent than those with benzylic substituents against genotype la polymerase. The most potent inhibitors contained small alkyl or carbocyclic substituents and exhibited IC50's of 50-100 and 200-400 nM against genotype 1 b and 1 a HCV polymerase, respectively. (c) 2005 Elsevier Ltd. All rights reserved.
• Potent and selective HIV-1 ribonuclease H inhibitors based on a 1-hydroxy-1,8-naphthyridin-2(1H)-one scaffold
  作者：Peter D. Williams、Donnette D. Staas、Shankar Venkatraman、H. Marie Loughran、Rowena D. Ruzek、Theresa M. Booth、Terry A. Lyle、John S. Wai、Joseph P. Vacca、Bradley P. Feuston、Linda T. Ecto、Jessica A. Flynn、Daniel J. DiStefano、Daria J. Hazuda、Carolyn M. Bahnck、Amy L. Himmelberger、Geetha Dornadula、Renee C. Hrin、Kara A. Stillmock、Marc V. Witmer、Michael D. Miller、Jay A. Grobler

  DOI：10.1016/j.bmcl.2010.08.135

  日期：2010.11

  Optimization studies using an HIV RNase H active site inhibitor containing a 1-hydroxy-1,8-naphthyridin-2(1H)-one core identified 4-position substituents that provided several potent and selective inhibitors. The best compound was potent and selective in biochemical assays (IC(50) = 0.045 mu M, HIV RT RNase H; 13 mu M, HIV RT-polymerase; 24 mu M, HIV integrase) and showed antiviral efficacy in a single-cycle viral replication assay in P4-2 cells (IC(50) = 0.19 mu M) with a modest window with respect to cytotoxicity (CC(50) = 3.3 mu M). (C) 2010 Elsevier Ltd. All rights reserved.
• ANTI-INFECTIVE AGENTS
  申请人：ABBOTT LABORATORIES

  公开号：EP1560827B1

  公开（公告）日：2010-12-29