6-chloro-1-hydroxy-3,5,8-trimethoxynaphthalene | 1204476-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-chloro-1-hydroxy-3,5,8-trimethoxynaphthalene
• 英文别名: 6-Chloro-3,5,8-trimethoxynaphthalen-1-ol
• CAS: 1204476-26-5
• 化学式: C₁₃H₁₃ClO₄
• 分子量: 268.697
• InChiKey: KKTZYWNIJOTCPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloro-1-hydroxy-3,5,8-trimethoxynaphthalene 在 四氯化钛 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 mineral oil 为溶剂， 反应 1.83h， 生成 8-chloro-2-methyl-5,7,10-trimethoxybenzo[h]chromen-4-one
  参考文献：
  名称：

  Synthesis and Biological Activities of Topopyrones

  摘要：

  Structure-activity studies were employed to investigate the stabilization of DNA-topoisomerases I and II covalent binary complexes by topopyrone analogues. The synthesis of five new topopyrone derivatives and study of their ability to stabilize DNA topoisomerase I and DNA-topoisomerase II covalent binary complexes are described. The biochemical assays suggest that the orientation of the fused 1,4-pyrone ring and halogen substituents contribute importantly to the overall potency of the topopyrones as topoisomerase poisons.

  DOI：

  10.1021/np200777z
• 作为产物：
  描述：

  toluene-4-sulfonic acid 6-chloro-3,5,8-trimethoxynaphthalen-1-yl ester 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以56%的产率得到6-chloro-1-hydroxy-3,5,8-trimethoxynaphthalene
  参考文献：
  名称：

  Synthesis and Biological Activities of Topopyrones

  摘要：

  Structure-activity studies were employed to investigate the stabilization of DNA-topoisomerases I and II covalent binary complexes by topopyrone analogues. The synthesis of five new topopyrone derivatives and study of their ability to stabilize DNA topoisomerase I and DNA-topoisomerase II covalent binary complexes are described. The biochemical assays suggest that the orientation of the fused 1,4-pyrone ring and halogen substituents contribute importantly to the overall potency of the topopyrones as topoisomerase poisons.

  DOI：

  10.1021/np200777z

文献信息

• Synthesis and Biological Activities of Topopyrones
  作者：Paul A. Zaleski、Rumit Maini、Simon J. Leiris、Mark A. Elban、Sidney M. Hecht

  DOI：10.1021/np200777z

  日期：2012.4.27

  Structure-activity studies were employed to investigate the stabilization of DNA-topoisomerases I and II covalent binary complexes by topopyrone analogues. The synthesis of five new topopyrone derivatives and study of their ability to stabilize DNA topoisomerase I and DNA-topoisomerase II covalent binary complexes are described. The biochemical assays suggest that the orientation of the fused 1,4-pyrone ring and halogen substituents contribute importantly to the overall potency of the topopyrones as topoisomerase poisons.