9,10-anthraquinone O-9-(4-fluorobenzoyl)oxime

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-anthraquinone O-9-(4-fluorobenzoyl)oxime
• 英文别名: [(10-Oxoanthracen-9-ylidene)amino] 4-fluorobenzoate
• 化学式: C₂₁H₁₂FNO₃
• 分子量: 345.33
• InChiKey: ZWJVPUVCYUTUSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  蒽醌 在 盐酸羟胺 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 9,10-anthraquinone O-9-(4-fluorobenzoyl)oxime
  参考文献：
  名称：

  Relationship Between Structure of Conjugated Oxime Esters and Their Ability to Cleave DNA

  摘要：

  The size and geometry of polycycles are critical to intercalation into DNA. This work involves the establishment of a new compound library that includes 35 O-benzoyl oxime esters with intercalators of five types. These conjugated compounds were synthesized by the condensation of substituted benzoyl chlorides (XC6H4COCl; X = H, Me, CN, F, and NO2) or naphthoyl chlorides with oximes of fluoren-9-one, 9,10-anthraquinone, xanthen-9-one, thioxanthen-9-one, and 9H-thioxanthen-9-one, 10,10-dioxide to give the corresponding esters in 80-99% yields. All of these compounds could cleave DNA when photolyzed by UV light. Of these conjugates, 9,10-anthraquinone-O-9-(4-fluorobenzoyl)oxime with a binding constant of 4.49 x 10(4) M-1 cleaved DNA most efficiently. Examination of the structure activity relationship supports a conclusion that two factors affect DNA-cleaving potency. These are (1) the planarity of the intercalating moiety, and (2) the size and substituents of the benzoyl ring. The DNA-cleaving ability followed the order 9,10-anthraquinone > fluoren-9-one >= xanthen-9-one similar to thioxanthen-9-one > 9H-thioxanthen-9-one 10,10-dioxide. The benzoyl-containing oxime ester conjugates were more active than the corresponding naphthoyl-containing conjugates. The potency that was associated with the different substituents on the benzoyl ring followed the order F > CN >= NO2 > Me similar to H.

  DOI：

  10.1021/bc400060h

文献信息

• Oxime esters of anthraquinone as photo-induced DNA-cleaving agents for single- and double-strand scissions
  作者：Jih Ru Hwu、Shwu-Chen Tsay、Shih Chin Hong、Yi-Jing Leu、Chih-Fen Liu、Shang-Shing P Chou

  DOI：10.1016/s0040-4039(03)00375-7

  日期：2003.3

  Anthraquinone-O-9-(4-cyanobenzoyl)oxime (13) with binding constant of 4.49x 10(4) M-1 exhibited single-strand scission of DNA at the concentration of 10 muM and double-strand scission at 50 muM upon UV irradiation. (C) 2003 Published by Elsevier Science Ltd.
• Relationship Between Structure of Conjugated Oxime Esters and Their Ability to Cleave DNA
  作者：Jih Ru Hwu、Shwu-Chen Tsay、Shih Chin Hong、Ming-Hua Hsu、Chih-Fen Liu、Shang-Shing P. Chou

  DOI：10.1021/bc400060h

  日期：2013.11.20

  The size and geometry of polycycles are critical to intercalation into DNA. This work involves the establishment of a new compound library that includes 35 O-benzoyl oxime esters with intercalators of five types. These conjugated compounds were synthesized by the condensation of substituted benzoyl chlorides (XC6H4COCl; X = H, Me, CN, F, and NO2) or naphthoyl chlorides with oximes of fluoren-9-one, 9,10-anthraquinone, xanthen-9-one, thioxanthen-9-one, and 9H-thioxanthen-9-one, 10,10-dioxide to give the corresponding esters in 80-99% yields. All of these compounds could cleave DNA when photolyzed by UV light. Of these conjugates, 9,10-anthraquinone-O-9-(4-fluorobenzoyl)oxime with a binding constant of 4.49 x 10(4) M-1 cleaved DNA most efficiently. Examination of the structure activity relationship supports a conclusion that two factors affect DNA-cleaving potency. These are (1) the planarity of the intercalating moiety, and (2) the size and substituents of the benzoyl ring. The DNA-cleaving ability followed the order 9,10-anthraquinone > fluoren-9-one >= xanthen-9-one similar to thioxanthen-9-one > 9H-thioxanthen-9-one 10,10-dioxide. The benzoyl-containing oxime ester conjugates were more active than the corresponding naphthoyl-containing conjugates. The potency that was associated with the different substituents on the benzoyl ring followed the order F > CN >= NO2 > Me similar to H.