2-amino-1-hydroxyphenanthrene | 56432-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2-amino-1-hydroxyphenanthrene
• 英文别名: 2-Amino-1-phenanthrol；1-Hydroxy-2-aminophenanthren；2-Amino-1-hydroxy-phenanthren；2-Aminophenanthren-1-ol；2-aminophenanthren-1-ol
• CAS: 56432-31-6
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: NOYQLZSZLJQHGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-1-hydroxyphenanthrene 在 吡啶 、 盐酸 、 氢氧化钾 、 碳酸氢钠 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 (S)-1-(3-aminopyrrolidin-1-yl)-2-fluoro-4-oxo-4H-pyrido[3,2,1-kl]naphtho[2,1-f]-phenoxazine-5-carboxylic acid hydrochloride
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Series of Fluoroquinoanthroxazines with Contrasting Dual Mechanisms of Action against Topoisomerase II and G-Quadruplexes

  摘要：

  Topoisomerase inhibitors are important and clinically effective drugs, while G-quadruplex-interactive compounds that disrupt telomere maintenance mechanisms have yet to be proven useful in the clinic. If G-quadruplex-interactive compounds are to be clinically useful, it will most likely be in combination with more established cytotoxic agents. We have previously reported on a family of topoisomerase II inhibitors that also interact with G-quadruplexes. On the basis of previously established structure-activity relationships (SARs) for compounds that are able to inhibit topoisomerase II or interact with G-quadruplex to varying degrees, we have now designed and synthesized four new fluoroquinoanthroxazines (FQAs) that have different profiles of mixed topoisomerase II poisoning effects and G-quadruplex interactions. The biological profiles of the four new compounds were determined with respect to G-quadruplex interaction (polymerase stop and photocleavage assays) and topoisomerase II interaction (DNA cleavage and kDNA decatenation assays), alongside cytotoxicity tests with matched pairs of topoisomerase II-resistant and topoisomerase II-sensitive cells and with telomerase (+) and ALT (+) cell lines (ALT = alternative lengthening of telomeres). From this study, we have identified two FQAs with sharply contrasting profiles of potent G-quadruplex interaction with a weak topoisomerase II poisoning effect, and vice versa, for further evaluation to determine the optimum combination of these activities in subsequent in vivo studies.

  DOI：

  10.1021/jm0203377
• 作为产物：
  描述：

  1-hydroxy-2-nitrophenanthrene 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 生成 2-amino-1-hydroxyphenanthrene
  参考文献：
  名称：

  Bogdanov,S.V.; Shibryaeva,L.S., Journal of General Chemistry of the USSR, 1961, vol. 31, p. 479 - 484

  摘要：

  DOI：

文献信息

• Design, Synthesis, and Biological Evaluation of a Series of Fluoroquinoanthroxazines with Contrasting Dual Mechanisms of Action against Topoisomerase II and G-Quadruplexes
  作者：Mu-Yong Kim、Wenhu Duan、Mary Gleason-Guzman、Laurence H. Hurley

  DOI：10.1021/jm0203377

  日期：2003.2.1

  Topoisomerase inhibitors are important and clinically effective drugs, while G-quadruplex-interactive compounds that disrupt telomere maintenance mechanisms have yet to be proven useful in the clinic. If G-quadruplex-interactive compounds are to be clinically useful, it will most likely be in combination with more established cytotoxic agents. We have previously reported on a family of topoisomerase II inhibitors that also interact with G-quadruplexes. On the basis of previously established structure-activity relationships (SARs) for compounds that are able to inhibit topoisomerase II or interact with G-quadruplex to varying degrees, we have now designed and synthesized four new fluoroquinoanthroxazines (FQAs) that have different profiles of mixed topoisomerase II poisoning effects and G-quadruplex interactions. The biological profiles of the four new compounds were determined with respect to G-quadruplex interaction (polymerase stop and photocleavage assays) and topoisomerase II interaction (DNA cleavage and kDNA decatenation assays), alongside cytotoxicity tests with matched pairs of topoisomerase II-resistant and topoisomerase II-sensitive cells and with telomerase (+) and ALT (+) cell lines (ALT = alternative lengthening of telomeres). From this study, we have identified two FQAs with sharply contrasting profiles of potent G-quadruplex interaction with a weak topoisomerase II poisoning effect, and vice versa, for further evaluation to determine the optimum combination of these activities in subsequent in vivo studies.
• Bogdanov,S.V.; Shibryaeva,L.S., Journal of General Chemistry of the USSR, 1961, vol. 31, p. 479 - 484
  作者：Bogdanov,S.V.、Shibryaeva,L.S.

  DOI：——

  日期：——