1-(2-ethylbutyl)-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione | 686263-14-9

• 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: 1-(2-ethylbutyl)-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione
• 英文别名: 1-(2-ethylbutyl)pyrido[2,3-d][1,3]oxazine-2,4-dione
• CAS: 686263-14-9
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: XBIYMWXRTIEGAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  379.0±34.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  59.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-ethylbutyl)-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione 在 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 7.0h， 生成 1-(2-Ethyl-butyl)-4-hydroxy-2-oxo-1,2-dihydro-[1,8]naphthyridine-3-carboxylic acid (2-sulfamoyl-phenyl)-amide
  参考文献：
  名称：

  Inhibitors of HCV NS5B polymerase: synthesis and structure–activity relationships of N-1-heteroalkyl-4-hydroxyquinolon-3-yl-benzothiadiazines

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.01.071
• 作为产物：
  描述：

  ethyl 2-[(2-ethylbutyl)amino]nicotinate 、 氯甲酸三氯甲酯 在 silica gel 、 ethyl acetate n-hexane 作用下， 以 1,2-二氯乙烷 、 1,4-二氧六环 为溶剂， 反应 16.0h， 以to provide the title compound (0.235 g, 36%)的产率得到1-(2-ethylbutyl)-2H-pyrido[2,3-d][1,3]oxazine-2,4(1H)-dione
  参考文献：
  名称：

  Anti-infective agents

  摘要：

  公式为1的化合物是丙型肝炎（HCV）聚合酶抑制剂。还披露了一种抑制丙型肝炎（HCV）聚合酶的组合物和方法，制备该化合物的过程以及用于该过程的合成中间体。

  公开号：

  US20040087577A1

文献信息

• ANTI-INFECTIVE AGENTS
  申请人：ABBOTT LABORATORIES

  公开号：EP1560827B1

  公开（公告）日：2010-12-29
• US7902203B2
  申请人：——

  公开号：US7902203B2

  公开（公告）日：2011-03-08
• 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。
• 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.