1-(2-Hydroxyethoxymethyl)-6-methoxy-4-oxo-quinoline-3-carboxylic acid | 877831-21-5

• 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: 1-(2-Hydroxyethoxymethyl)-6-methoxy-4-oxo-quinoline-3-carboxylic acid
• 英文别名: 1-(2-hydroxyethoxymethyl)-6-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 877831-21-5
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: IZBGKENGDDDHJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Ethyl 1-(2-hydroxyethoxymethyl)-6-methoxy-4-oxo-quinoline-3-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以58%的产率得到1-(2-Hydroxyethoxymethyl)-6-methoxy-4-oxo-quinoline-3-carboxylic acid
  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

• 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.