8-fluoro-5-hydroxy-7-methyl-1,4-naphthoquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-fluoro-5-hydroxy-7-methyl-1,4-naphthoquinone
• 英文别名: 5-fluoro-8-hydroxy-6-methylnaphthalene-1,4-dione
• 化学式: C₁₁H₇FO₃
• 分子量: 206.173
• InChiKey: AKINMNDPQRFSNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  马来酸酐 、 4-氟-3-甲基苯酚 在 aluminum (III) chloride 、 sodium chloride 作用下， 反应 0.03h， 以25%的产率得到8-fluoro-5-hydroxy-7-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  1,4-萘醌衍生物的合成及HIV-1逆转录酶抑制活性

  摘要：

  合成了一些 1,4-萘醌衍生物，并从 Euclea natalensis 的根中分离出 5-hydroxy-7-methyl-1,4-naphthoquinone (5) 的二聚体。通过光谱（UV、IR、NMR和MS）分析证实了它们的结构。使用罗氏诊断试剂盒在体外（非放射性 HIV-RT 比色分析）研究了化合物对重组 HIV-1 酶的 HIV-1 逆转录酶抑制活性，并与作为标准药物的阿霉素进行了比较。一些合成的化合物在 100 μg/mL 浓度下表现出异常有效的 (91–100%) HIV-1 RT 抑制。令人惊讶的是，二聚体显示出非常弱的活性。

  DOI：

  10.1007/s10600-012-0094-7

文献信息

• Synthesis and HIV-1 reverse transcriptase inhibition activity of 1,4-naphthoquinone derivatives
  作者：Anita Mahapatra、T. E. Tshikalange、J. J. M. Meyer、Namrita Lall

  DOI：10.1007/s10600-012-0094-7

  日期：2012.1

  Some 1,4-napthoquinone derivatives were synthesized, and dimers of 5-hydroxy-7-methyl-1,4-naphthoquinone (5) were isolated from the roots of Euclea natalensis. Their structures were confirmed by spectroscopic (UV, IR, NMR, and MS) analysis. The HIV-1 reverse transcriptase inhibition activity of the compounds against recombinant HIV-1 enzyme was studied in vitro (non-radioactive HIV-RT colorimetric

  合成了一些 1,4-萘醌衍生物，并从 Euclea natalensis 的根中分离出 5-hydroxy-7-methyl-1,4-naphthoquinone (5) 的二聚体。通过光谱（UV、IR、NMR和MS）分析证实了它们的结构。使用罗氏诊断试剂盒在体外（非放射性 HIV-RT 比色分析）研究了化合物对重组 HIV-1 酶的 HIV-1 逆转录酶抑制活性，并与作为标准药物的阿霉素进行了比较。一些合成的化合物在 100 μg/mL 浓度下表现出异常有效的 (91–100%) HIV-1 RT 抑制。令人惊讶的是，二聚体显示出非常弱的活性。
• Activity of 7-methyljuglone derivatives against Mycobacterium tuberculosis and as subversive substrates for mycothiol disulfide reductase
  作者：Anita Mahapatra、Sannah P.N. Mativandlela、B. Binneman、P.B. Fourie、Chris J. Hamilton、J.J.M. Meyer、F. van der Kooy、Peter Houghton、Namrita Lall

  DOI：10.1016/j.bmc.2007.08.064

  日期：2007.12

  The naphthoquinone 7-methyljuglone (5-hydroxy-7-methyl-1,4-naphthoquinone) has previously been isolated and identified as an active component of root extracts of Euclea natalensis which displays antitubercular activity. Herein, a series of synthetic and plant-derived naphthoquinone derivates of the 7-methyljuglone scaffold have been prepared and evaluated for antibacterial activity against Mycobacterium tuberculosis. Several of these compounds have been shown to operate as subversive substrates with mycothiol disulfide reductase. The absence of a direct correlation between antitubercular activity and subversive substrate efficiency with mycothiol disulfide reductase, might be a consequence of their non-specific reactivity with multiple biological targets (e. g. other disulfide reductases). (c) 2007 Elsevier Ltd. All rights reserved.
• Cytotoxicity of synthesized 1,4-naphthoquinone analogues on selected human cancer cell lines
  作者：Navneet Kishore、Brigitte Binneman、Anita Mahapatra、Maryna van de Venter、Debbie du Plessis-Stoman、Gerhardt Boukes、Peter Houghton、J.J. Marion Meyer、Namrita Lall

  DOI：10.1016/j.bmc.2014.06.013

  日期：2014.9

  In an effort to establish new candidates with enhanced anticancer activity of 5-hydroxy-7-methyl-1,4-naphthoquinone scaffold (7-methyljuglone) previously isolated from the root extract of Euclea natalensis, a series of 7-methyljuglone derivatives have been synthesized and assessed for cytotoxicity on selected human cancer lines. These compounds were screened in vitro for anticancer activity on MCF-7, HeLa, SNO and DU145 human cancer cell lines by MTT assay. Most of them exhibited significant toxicity on cancer cell lines with lower IC50 values. The most potent derivative (19) exhibited the toxicity on HeLa and DU145 cell lines with IC50 value of 5.3 and 6.8μM followed by compound (5) with IC50 value of 10.1 and 9.3μM, respectively. Structure-activity relationship reveals that the fluoro substituents at position C-8 while hydroxyl substituents at C-2 and C-5 positions played an important role in toxicity.