2-Bromo-7-(4-methylpentyl)-1,4-naphthoquinone | 500217-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Bromo-7-(4-methylpentyl)-1,4-naphthoquinone
• 英文别名: 2-Bromo-7-(4-methylpentyl)naphthalene-1,4-dione
• CAS: 500217-78-7
• 化学式: C₁₆H₁₇BrO₂
• 分子量: 321.214
• InChiKey: FWKVATGUFWVFAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-7-(4-methylpentyl)-1,4-naphthoquinone 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以100%的产率得到1,4-Naphthalenedione, 2-hydroxy-7-(4-methylpentyl)-
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones

  摘要：

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.

  DOI：

  10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m
• 作为产物：
  描述：

  1,4-Naphthalenedione, 5,8-dihydro-6-(4-methyl-3-pentenyl)- 在 Lindlar's catalyst manganese(IV) oxide 、 氢气 、 溴 、 碳酸氢钠 作用下， 以 乙醇 、 溶剂黄146 、 乙酸乙酯 、 苯 为溶剂， 反应 100.33h， 生成 2-Bromo-7-(4-methylpentyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones

  摘要：

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.

  DOI：

  10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m

文献信息

• Synthesis and cytotoxicity of new aminoterpenylquinones
  作者：José M. Miguel del Corral、M Angeles Castro、Marina Gordaliza、M Luz Martı́n、Simone A. Gualberto、Ana M Gamito、Carmen Cuevas、Arturo San Feliciano

  DOI：10.1016/j.bmc.2004.10.059

  日期：2005.2

  Several 6(7)-alkyl-1,4-naphthoquinones (NQ) have been prepared by cycloaddition reactions between the monoterpene alpha-myrcene and p-benzoquinones and halogen and nitrogen-containing functional groups have been introduced at the C-2 position of the naphthoquinone ring via nucleophilic addition or substitution reactions. These substituents at positions 2/3 of the NQ clearly influence the cytotoxic

  通过单萜α-月桂烯和对苯醌之间的环加成反应，已经制备了几种6（7）-烷基-1,4-萘醌（NQ），并且在C-2位引入了卤素和含氮官能团。萘醌环通过亲核加成或取代反应。NQ位置2/3处的这些取代基明显影响此类化合物的细胞毒性。特别令人感兴趣的是被芳基氨基，特别是对-氧芳基氨基，基团取代，其大大增强了它们的生物活性和选择性。
• Synthesis and Biological Evaluation of Cytotoxic 6(7)-Alkyl-2-hydroxy-1, 4-naphthoquinones
  作者：José M. Miguel del Corral、Maria Angeles Castro、Marina Gordaliza、Maria Luz Martin、Alaide B. Oliveira、Simone A. Gualberto、Maria Dolores García-Grávalos、Arturo San Feliciano

  DOI：10.1002/1521-4184(200212)335:9<427::aid-ardp427>3.0.co;2-m

  日期：2002.12

  Various Diels Alder cycloaddition conditions have been used to optimise the preparation of cytotoxic 6-alkyl-1,4-naphthoquinones, which were subsequently transformed into 6(7)-alkyl-2-hydroxy-1,4-naphthoquinones. The compounds thus prepared were evaluated for their cytotoxic activity against several neoplastic cultured cell lines and some of them showed IC50 values below the muM level.