6-fluoro-1,4-dihydro-1-<(2-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid | 136471-88-0

• 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: 6-fluoro-1,4-dihydro-1-<(2-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 6-Fluoro-1-(2-hydroxyethoxymethyl)-4-oxo-quinoline-3-carboxylic acid；6-fluoro-1-(2-hydroxyethoxymethyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 136471-88-0
• 化学式: C₁₃H₁₂FNO₅
• 分子量: 281.24
• InChiKey: GMOPFWYXDQWRNB-UHFFFAOYSA-N

物化性质

• 沸点：
  482.7±45.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-fluoro-1,4-dihydro-1-<(2-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid 、 乙酸乙酯 在 Amano PS Lipase 作用下， 以 乙酸乙酯 为溶剂， 反应 72.0h， 以87%的产率得到1-(2-acetyloxyethoxymethyl)-6-fluoro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Lipase-Mediated Acylation of Acyclonucleosides. Application to Novel Fluoroquinolone Derivatives

  摘要：

  A novel kind of acyclonucleoside derived from fluoroquinolones is described. Lipases have been used to prepare acyl derivatives under mild conditions and in good yields.

  DOI：

  10.1080/00397919108016421
• 作为产物：
  描述：

  6-氟-4-氧代-1,4-二氢-3-喹啉羧酸乙酯 在 sodium hydroxide 、 三甲基氯硅烷 、 四氯化锡 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 6-fluoro-1,4-dihydro-1-<(2-hydroxyethoxy)methyl>-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Cruz, A. de la; Elguero, J.; Goya, P., Journal of Chemical Research, Miniprint, 1992, # 7, p. 1682 - 1693

  摘要：

  DOI：

文献信息

• Synthesis and anti-HSV-1 activity of quinolonic acyclovir analogues
  作者：Bianca d’A. Lucero、Claudia Regina B. Gomes、Izabel Christina de P.P. Frugulhetti、Letícia V. Faro、Lise Alvarenga、Maria Cecília B.V. de Souza、Thiago M.L. de Souza、Vitor F. Ferreira

  DOI：10.1016/j.bmcl.2005.10.111

  日期：2006.2

  Several 1-[(2-hydroxy-ethoxy)methyl]-3-carbethoxy-4(1H)quinolones (2a-1) and 1-[(2-hydroxy-ethoxy)methyl]-4(1H) quinolone-3-carboxylic acids (3a-j and 31) were synthesized and 2a-j, 21 and 3a-j, 31 were evaluated against herpes simplex virus type 1 (HSV-1), employing a one-pot reaction: sitylation of the desired quinolone (BSTFA 1% TMCS) followed by equiniolar amount addition of 1,3-dioxolane, chlorotrimethylsilane and KI, at room temperature. The acyclonucleosides 2a-1 were obtained in 40-77% yields. The esters 2a-j and 21 were subsequently converted into the corresponding hydroxyacids 3 in 40-70% yields. Attempts of hydrolysis of 2k produced only a mixture of degradation products. Antiviral activity of 2 and 3 on HSV-1 virus infection was assessed by the virus yield assay. Except for compounds 2i and 3e, the acyclonucleosides were found to reduce the virus yield by 70-99% at the concentration of 50 mu M, being the acids, in general, more effective inhibitors than their corresponding esters. Compounds 3j and 2d exhibited antiviral activity against HSV-1 virus with EC50 of 0.7 +/- 0.04 and 0.8 +/- 0.09 mu M, respectively. Both compounds were not toxic towards the Vero cell line. (c) 2005 Elsevier Ltd. All rights reserved.
• Cruz, A. de la; Elguero, J.; Goya, P., Journal of Chemical Research, Miniprint, 1992, # 7, p. 1682 - 1693
  作者：Cruz, A. de la、Elguero, J.、Goya, P.、Martinez, A.、Gotor, V.、et al.

  DOI：——

  日期：——
• Lipase-Mediated Acylation of Acyclonucleosides. Application to Novel Fluoroquinolone Derivatives
  作者：Angeles de la Cruz、José Elguero、Vicente Gotor、Pilar Goya、Ana Martínez、Francisco Moris

  DOI：10.1080/00397919108016421

  日期：1991.7

  A novel kind of acyclonucleoside derived from fluoroquinolones is described. Lipases have been used to prepare acyl derivatives under mild conditions and in good yields.