4-[(2-Cyclopropylethynyl)oxy]-3-ethyl-6-fluoro-2(1H)-quinolinone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[(2-Cyclopropylethynyl)oxy]-3-ethyl-6-fluoro-2(1H)-quinolinone
• 英文别名: 4-(2-cyclopropylethynoxy)-3-ethyl-6-fluoro-1H-quinolin-2-one
• 化学式: C₁₆H₁₄FNO₂
• 分子量: 271.291
• InChiKey: ORNTVNQQVUITLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-(chlorocarbonyl)butanoate 在 甲烷磺酸 、 acidic resin AG 50W-X₄ 、 phosphorus pentoxide 、 lithium 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-[(2-Cyclopropylethynyl)oxy]-3-ethyl-6-fluoro-2(1H)-quinolinone
  参考文献：
  名称：

  Design of Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase with Improved Drug Resistance Properties. 2.

  摘要：

  HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs) are part of the combination therapy currently used to treat HIV infection. The features of a new NNRTI drug for HIV treatment must include selective potent activity against both wild-type virus as well as against mutant virus that have been selected by use of current antiretroviral treatment regimens. Based on analogy with known HIV-1 NNRTI inhibitors and modeling studies utilizing the X-ray crystal structure of inhibitors bound in the HIV-1 RT, a series of substituted 2-quinolones was synthesized and evaluated as HIV-1 inhibitors.

  DOI：

  10.1021/jm040072r

文献信息

• Quinolone compounds for use in treating viral infections
  申请人：——

  公开号：US20030069271A1

  公开（公告）日：2003-04-10

  The present invention relates to quinolone compounds and their use in the treatment of viral infections.

  本发明涉及喹诺酮化合物及其在治疗病毒感染中的应用。
• QUINOLONE COMPOUNDS FOR USE IN TREATING VIRAL INFECTIONS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1244629A2

  公开（公告）日：2002-10-02
• [EN] QUINOLONE COMPOUNDS FOR USE IN TREATING VIRAL INFECTIONS<br/>[FR] COMPOSES DE QUINOLONE UTILISES DANS LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：GLAXO GROUP LTD

  公开号：WO2001046150A2

  公开（公告）日：2001-06-28

  The present invention relates to quinolone compounds, such as compounds of formula (Ia) wherein: R1 is hydrogen; R2 is oxygen or sulfur; R3 is trifluoromethyl; cyano; C¿1-8?alkyl optionally substituted with C1-8alkyl or trifluoromethyl; or OR?15¿, wherein R15 is C¿1-8?alkyl optionally substituted with C1-8alkyl; R?4 is OR11¿, wherein R11 is C¿2-8?alkenyl optionally substituted with C1-8alkyl; C1-8alkyl optionally substituted with C1-8alkyl; C6-14arylalkyl; C3-6cycloalkyl; C3-6cycloalkylalkyl; heterocyclealkyl; heterocyclealkynyl; C3-6cycloalkylalkenyl; C6-14arylalkynyl; C3-6cycloalkylalkynyl; SR?12¿, wherein R12 is C¿3-6?cycloalkyl; S(O)R?12¿, wherein R12 is C¿3-6?cycloalkyl; or NR?13R14¿ wherein R?13 and R14¿, which may be the same or different, are hydrogen or C¿1-8?alkyl, optionally substituted with C1-8alkyl; R?5¿ is hydrogen; nitro; halogen; C¿1-8?alkyl, optionally substituted with C1-8alkyl or trifluoromethyl; R?6¿ is hydrogen; halogen; C¿1-8?alkyl; cyano: trifluoromethyl; or OR?10¿ wherein R10 is C¿1-8?alkyl or trifluoromethyl; R?7¿ is hydrogen; C¿1-8?alkyl; halogen; C6-14aryl; C1-8alkylaryl; C2-8alkynyl; heteroaryl; or OR?9¿ wherein R9 is C¿1-8?alkyl; R?8¿ is hydrogen; halogen; cyano; nitro; or OR16, wherein R16 is hydrogen or C¿1-8?alkyl optionally substituted with C1-8alkyl or trifluoromethyl; and their use in the treatment of viral infections.