2-(3-bromo-4-hydroxyphenyl)imidazolo[4,5-f][1,10]phenanthroline | 1382969-54-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(3-bromo-4-hydroxyphenyl)imidazolo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(3-bromo-4-hydroxyphenyl)imidazo[4,5-f][1,10]phenanthroline；2-bromo-4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol
• CAS: 1382969-54-1
• 化学式: C₁₉H₁₁BrN₄O
• 分子量: 391.227
• InChiKey: HMFHHLRGKNUJSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 ammonium hexafluorophosphate 、 2-(3-bromo-4-hydroxyphenyl)imidazolo[4,5-f][1,10]phenanthroline 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 以72%的产率得到[Ir(ppy)₂(BHIP)]PF₆
  参考文献：
  名称：

  Studies of anticancer activity in vitro and in vivo of iridium(III) polypyridyl complexes-loaded liposomes as drug delivery system

  摘要：

  Two iridium(III) polypyridyl complexes [Ir(ppy)(2)(HPIP)](PF6)(Ir-1), [Ir(ppy)(2)(BHPIP)](PF6)(Ir-2) and their liposomes Ir-1-Lipo and Ir-2-Lipo were synthesized and characterized by elemental analysis, IR, H-1 NMR and C-13 NMR. The anticancer activity in vitro and in vivo was evaluated. The cytotoxic activity in vitro of the complexes and their liposomes Ir-1-Lipo and Ir-2-Lipo against cancer cells was investigated by MTT methods. Ir-1 and Ir-2 show no cytotoxic activity, while Ir-1-Lipo and Ir-2-Lipo exhibit high cytotoxic effect. The IC50 values range from 5.2 +/- 0.8 to 22.3 +/- 1.8 mu M. The apoptosis, reactive oxygen species, the change of mitochondrial membrane potential, intracellular Ca2+ levels and a release of cytochrome c were investigated. The effect of Ir-1-Lipo and Ir-2-Lipo on microtubules was also explored. In the C57BL/6 mice model, Ir-1 only displays a tumor inhibitory rate of 23.21%, while lr-1-Lipo exhibits satisfactory in vivo antitumor efficacy with tumor inhibitory rate of 72.55%. This study demonstrates that complexes encapsulated in liposomes induce apoptosis in B16 through ROS-mediated lysosomal-mitochondria dysfunction, inhibition of polymerization of microtubules and induce cell cycle arrest at S phase. (C) 2019 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.06.009
• 作为产物：
  描述：

  1,10-邻二氮杂菲-5,6-二酮 、 3-溴-4-羟基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 反应 2.0h， 以80%的产率得到2-(3-bromo-4-hydroxyphenyl)imidazolo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  钌 (II) 复合物的合成、表征、光裂解、体外细胞毒性、细胞凋亡和细胞周期停滞

  摘要：

  合成了两种新的钌 (II) 配合物 [Ru(dmp)2(BHIP)]2+ (1) 和 [Ru(dmb)2(BHIP)]2+ (2)，并通过元素分析、ESI-质谱和 1 H NMR。这些复合物与小牛胸腺 DNA (ct-DNA) 的 DNA 结合常数被确定为 2.09 (±0.18) × 104 (mol L−1)−1 (s = 2.58) 和 1.48 (±0.17) × 105 ( mol L−1)−1 (s = 1.57)，分别。粘度测量表明 1 和 2 通过嵌入与 ct-DNA 相互作用。在 365 nm 照射下，1 和 2 诱导 pBR322 DNA 的裂解。这些复合物的细胞毒性通过 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四唑 (MTT) 测定进行评估。通过流式细胞术研究复合物诱导的细胞凋亡。细胞周期阻滞结果表明2可抑制G0/G1期BEL-7402细胞的增殖。

  DOI：

  10.1080/00958972.2012.680592

文献信息

• Ruthenium complex containing alkynyl group, method of synthesizing the same and use thereof
  申请人：GUANGDONG PHARMACEUTICAL UNIVERSITY

  公开号：US11420990B2

  公开（公告）日：2022-08-23

  A Ruthenium complex containing alkynyl group, a method of synthesizing the Ruthenium complex containing alkynyl group and a use thereof are provided. The Ruthenium complex has a chemical formula of Ru(L)2(DPPZ′). DPPZ′ is a main ligand having structural formula of R is any one selected from the group consisting of H, substituted or unsubstituted phenyl, R1NH2, R1OH, and SiMe3; R1 is C1-C5 chain alkyl group; L is an auxiliary ligand with N as coordinating atom. Sonogashira coupling reaction is utilized to introduce alkynyl group into a DPPZ-type Ruthenium complex; the introduced alkynyl group is beneficial to promote the transmembrane absorption of drug molecules, increase the probability of drug entry into cells, and can also increase efficacy and reduce toxic and side effects of drugs. The Ruthenium complex provided has significant anti-tumor activity, especially anti-breast cancer activity, and can provide new ideas for designing anti-tumor drug molecules in the future.

  提供了一种含有炔基的钌络合物、一种合成含有炔基的钌络合物的方法及其用途。钌络合物的化学式为 Ru(L)2(DPPZ′)。DPPZ′ 是一种主配体，其结构式为 R 是选自 H、取代或未取代的苯基、R1NH2、R1OH 和 SiMe3 组成的组中的任意一个；R1 是 C1-C5 链烷基；L 是以 N 为配位原子的辅助配体。利用 Sonogashira 偶联反应将炔基引入到 DPPZ 型钌络合物中，引入的炔基有利于促进药物分子的跨膜吸收，增加药物进入细胞的几率，还可以增加药效，降低药物的毒副作用。所提供的钌络合物具有显著的抗肿瘤活性，尤其是抗乳腺癌活性，可为今后设计抗肿瘤药物分子提供新思路。
• RUTHENIUM COMPLEX CONTAINING ALKYNYL GROUP, METHOD OF SYNTHESIZING THE SAME AND USE THEREOF
  申请人：GUANGDONG PHARMACEUTICAL UNIVERSITY

  公开号：US20210246154A1

  公开（公告）日：2021-08-12

  A Ruthenium complex containing alkynyl group, a method of synthesizing the Ruthenium complex containing alkynyl group and a use thereof are provided. The Ruthenium complex has a chemical formula of Ru(L) 2 (DPPZ′). DPPZ′ is a main ligand having structural formula of R is any one selected from the group consisting of H, substituted or unsubstituted phenyl, R 1 NH 2 , R 1 OH, and SiMe 3 ; R 1 is C1-C5 chain alkyl group; L is an auxiliary ligand with N as coordinating atom. Sonogashira coupling reaction is utilized to introduce alkynyl group into a DPPZ-type Ruthenium complex; the introduced alkynyl group is beneficial to promote the transmembrane absorption of drug molecules, increase the probability of drug entry into cells, and can also increase efficacy and reduce toxic and side effects of drugs. The Ruthenium complex provided has significant anti-tumor activity, especially anti-breast cancer activity, and can provide new ideas for designing anti-tumor drug molecules in the future.