Ethyl 6-fluoro-4-oxo-1-trimethylsilylquinoline-3-carboxylate | 1027958-73-1

• 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: Ethyl 6-fluoro-4-oxo-1-trimethylsilylquinoline-3-carboxylate
• CAS: 1027958-73-1
• 化学式: C₁₅H₁₈FNO₃Si
• 分子量: 307.397
• InChiKey: YESXPZOIUFVCEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 6-fluoro-4-oxo-1-trimethylsilylquinoline-3-carboxylate 在 sodium hydroxide 、 Amano PS Lipase 、 四氯化锡 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 72.0h， 生成 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：

  N,O-双(三甲基硅烷基)三氟乙酰胺 、 6-氟-4-氧代-1,4-二氢-3-喹啉羧酸乙酯 在 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 Ethyl 6-fluoro-4-oxo-1-trimethylsilylquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and anti-HSV-1 activity of quinolonic acyclovir analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2005.10.111

文献信息

• Cruz, Angeles de la; Elguero, Jose; Goya, Pilar, Journal of the Chemical Society. Perkin transactions I, 1993, # 7, p. 845 - 850
  作者：Cruz, Angeles de la、Elguero, Jose、Goya, Pilar、Martinez, Ana、Clercq, Erik De

  DOI：——

  日期：——
• 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.
• 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.