2-(5-chlorothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline | 1514799-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(5-chlorothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline
• CAS: 1514799-60-0
• 化学式: C₁₇H₉ClN₄S
• 分子量: 336.804
• InChiKey: KZFNFJAAGSOQQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.46
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(5-chlorothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline 、 Λ-[Ru(II)(2,2′-bipyridine)₂(pyridine)₂][O,O′-dibenzoyl-L-tartrate]*12H₂O 、 sodium perchlorate 以 水 、 乙二醇 为溶剂， 反应 8.0h， 以61%的产率得到Λ-[Ru(II)(2,2′-bipyridine)₂(2-(5-chlorothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline)](ClO4)₂*2H₂O
  参考文献：
  名称：

  Dual topoisomerase I and II poisoning by chiral Ru(II) complexes containing 2-thiophenylimidazo[4,5-f][1,10]phenanthroline derivatives

  摘要：

  A series of chiral Ru(II) complexes bearing thiophene ligands were synthesized and characterized. Both Ru(II) complexes Delta/Lambda-[Ru(bpy)(2)(pscl)](2+) (Delta/Lambda-1) and Delta/Lambda-[Ru(bpy)(2)(psbr)](2+) (Delta/Lambda-2) (bpy = 2,2'-bipyridine, pscl = 2(5-chlorothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline, psbr = 2-(5-bromothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline) showed antitumor activities against A549, HepG2 and BEL-7402 tumor cell lines, especially HeLa tumor cell line. Moreover, Delta enantiomers were more active than Lambda enantiomers, accounting for the different cellular uptake. In addition, with the extension of time, these enantiomers could finally accumulate in the nucleus, suggesting that nucleic acids were the cellular target of these enantiomers. The DNA-binding behaviors of complexes were studied using spectroscopic and viscosity measurements. Results suggested that four complexes could bind to DNA in an intercalative mode but no obvious DNA-binding selectivity between the enantiomers was observed. Topoisomerase inhibition and DNA religation assay confirmed that four complexes acted as efficient dual topoisomerase I and II poisons, DNA strand breaks had also been observed from alkaline single cell gel electrophoresis (comet assay). Delta-1 and Delta-2 inhibited the growth of HeLa cells through the induction of apoptotic cell death, as evidenced by the Alexa Fluor (R) 488 annexin V staining assays and flow cytometry analysis. The results demonstrated that Delta/Lambda-1 and Delta/Lambda-2 acted as dual topoisomerase I and II poisons and caused DNA damage that could lead to cell cycle arrest by apoptosis. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2013.09.015
• 作为产物：
  描述：

  5-氯噻吩-2-甲醛 、 1,10-邻二氮杂菲-5,6-二酮 在 ammonium acetate 、 溶剂黄146 作用下， 反应 4.0h， 以81%的产率得到2-(5-chlorothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Dual topoisomerase I and II poisoning by chiral Ru(II) complexes containing 2-thiophenylimidazo[4,5-f][1,10]phenanthroline derivatives

  摘要：

  A series of chiral Ru(II) complexes bearing thiophene ligands were synthesized and characterized. Both Ru(II) complexes Delta/Lambda-[Ru(bpy)(2)(pscl)](2+) (Delta/Lambda-1) and Delta/Lambda-[Ru(bpy)(2)(psbr)](2+) (Delta/Lambda-2) (bpy = 2,2'-bipyridine, pscl = 2(5-chlorothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline, psbr = 2-(5-bromothiophen-2-yl)imidazo[4,5-f][1,10]phenanthroline) showed antitumor activities against A549, HepG2 and BEL-7402 tumor cell lines, especially HeLa tumor cell line. Moreover, Delta enantiomers were more active than Lambda enantiomers, accounting for the different cellular uptake. In addition, with the extension of time, these enantiomers could finally accumulate in the nucleus, suggesting that nucleic acids were the cellular target of these enantiomers. The DNA-binding behaviors of complexes were studied using spectroscopic and viscosity measurements. Results suggested that four complexes could bind to DNA in an intercalative mode but no obvious DNA-binding selectivity between the enantiomers was observed. Topoisomerase inhibition and DNA religation assay confirmed that four complexes acted as efficient dual topoisomerase I and II poisons, DNA strand breaks had also been observed from alkaline single cell gel electrophoresis (comet assay). Delta-1 and Delta-2 inhibited the growth of HeLa cells through the induction of apoptotic cell death, as evidenced by the Alexa Fluor (R) 488 annexin V staining assays and flow cytometry analysis. The results demonstrated that Delta/Lambda-1 and Delta/Lambda-2 acted as dual topoisomerase I and II poisons and caused DNA damage that could lead to cell cycle arrest by apoptosis. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2013.09.015