6541-19-1Relevant articles and documents
Synthesis of aminovinyl derivatives of quinoline- and isoquinoline-5,8- diones
Batenko,Popova,Belyakov,Valters
, p. 888 - 891 (2012)
Aminovinyl derivatives of quinoline-5,8-dione and isoquinoline-5,8-dione were obtained. The structure of (E)-6-chloro-7-[2-(N,N-diethylamino)vinyl] quinoline-5,8-dione was confirmed by X-ray structural analysis.
Quinoline-: Para -quinones and metals: Coordination-assisted formation of quinoline- ortho -quinones
Kubanik, Mario,Lam, Nelson Y. S.,Holtkamp, Hannah U.,S?hnel, Tilo,Anderson, Robert F.,Jamieson, Stephen M. F.,Hartinger, Christian G.
, p. 992 - 995 (2018)
The reaction of the para-quinone 6,7-dichloroquinoline-5,8-dione with various transition metal dimers led to the unexpected formation of quinoline-ortho-quinone metal complexes. Systematic variation of the reaction conditions helped identify the solvent a
Structure based design, synthesis, and evaluation of anti-CML activity of the quinolinequinones as LY83583 analogs
Ciftci, Halil I.,Fujita, Mikako,Otsuka, Masami,Sever, Belgin,Tateishi, Hiroshi,Bayrak, Nilüfer,Tuyun, Ama? Fatih,Y?ld?r?m, Hatice,Y?ld?z, Mahmut
, (2021)
Quinone-based small molecules are the promising structures for antiproliferative drug design and can induce apoptosis in cancer cells. Among them, one of the quinolinequinones, named as 6-anilino-5,8-quinolinequinone, LY83583 has the ability to inhibit the growth of cancer cells as an inhibitor of cyclase. The biological potential of all synthesized compounds as the analogs of the identified lead molecule LY83583 that possessed the antiproliferative efficiency was determined. The two series of the LY83583 analogs containing electron-withdrawing or electron-donating group(s) were synthesized and subsequently in vitro evaluated for their cytotoxic activity against K562, Jurkat, MT-2, and HeLa cell lines using MTT assay. All the LY83583 analogs showed antiproliferative activity with good IC50 values (less than positive control imatinib). Four analogs from each series were also selected for the determination of selectivity against human peripheral blood mononuclear cells (PBMCs). The analog AQQ15 showed high potency towards all cancer cell lines with almost similar selectivity of imatinib. In order to get a better insight into cytotoxic effects of the analog AQQ15 in K562 cells, further apoptotic effects due to annexin V/ethidium homodimer III staining, ABL1 kinase inhibition, and DNA cleaving ability were examined. The analog AQQ15 induced apoptotic cell death in K562 cells with 34.6% compared to imatinib (6.5%). This analog showed no considerable ABL1 kinase inhibitory activity but significant DNA cleavage activity indicating DNA fragmentation-induced apoptosis. Besides, molecular docking studies revealed that the analog AQQ15 established proper interactions with the deoxyribose sugar attached with the nucleobases adenine and guanidine respectively, in the minor groove of the double helix of DNA. In silico predicted pharmacokinetic parameters of this analog were found to comply with the standard range making it an efficient anticancer drug candidate for further research.
Synthesis of a novel platinum(II) complex with 6,7-dichloro-5,8-quinolinedione and the study of its antitumor mechanism in testicular seminoma
Li, Zitaiyu,Zhou, Jun,Gan, Yu,Yin, Yinghao,Zhang, Wuchao,Yang, Jianfu,Tang, Yuxin,Dai, Yingbo
, (2019)
A new platinum(II) complex, [Pt(ClClQ)(DMSO)Cl] (1), utilizing 6,7-dichloro-5,8-quinolinedione (ClClQ) as a ligand, has been synthesized and fully characterized. Single-crystal X-ray diffraction and other spectroscopic and analytical methods revealed that the coordination geometry of Pt(II) in complex 1 can also be described as a four-coordinated square planar geometry. The aim of the study was to explore the in vitro anticancer properties of complex 1. Our studies showed that complex 1 can regulate the viability of testicular seminoma cells in vitro, including cell proliferation and apoptosis. We further observed negative regulation by complex 1 of the expression levels of the key elements in the phosphoinositide-3 kinase (PI3K)/protein kinase B (Akt)/glycogen synthase kinase-3β (GSK3β) pathway, including phosphorylated phosphoinositide-3 kinase (p-PI3K), phosphorylated protein kinase B(p-Akt) and phosphorylated glycogen synthase kinase-3β (p-GSK3β). Moreover, the negative effect of complex 1 was reversed by LiCl, a GSK3β-specific inhibitor of the PI3K signaling pathway. Meanwhile, the levels of Bcl2 associated death promoter (Bad), cytochrome c, active-caspase-3 and active-caspase-9 increased significantly. In conclusion, we observed that complex 1 can regulate the viability of testicular seminoma cells through the PI3K/Akt/GSK3β signaling pathway and the mitochondria-mediated apoptotic pathway in vitro, and thus, complex 1 may have potential for use as a drug in the treatment of testicular germ cell tumors.
Transition metal complexes with 6,7-dichloro-5,8-quinolinedione as mitochondria-targeted anticancer agents
Huang, Xiao-Ling,Liang, Hong,Qin, Qi-Pin,Tan, Ming-Xiong,Wang, Zhen-Feng,Wu, Xue-Yu,Zou, Bi-Qun
, (2020)
Herein, a series of transition metal complexes, [Zn(DQ)2(CH3OH)2] (1), [Zn(DMQ)2(CH3OH)2] (2), [Co(DQ)2(CH3OH)2] (3), [Co(DMQ)2(CH3OH)2] (4), [Ni(DQ)2(CH3OH)2] (5), [Cu(DMQ)2(CH3OH)2] (6), [Mn(DQ)2(H2O)2] (7) and [Mn(DMQ)2(H2O)2] (8), containing 6,7-dichloro-5,8-quinolinedione (DQ) and 6,7-dichloro-2-methyl-5,8-quinolinedione (DMQ) ligands have been synthesized and characterized as potential antitumor agents. These complexes 1–8 exhibited evident anti-tumor activity in HeLa (cervical), MCF-7 (breast), Hep-G2 (hepatoma), T-24 (bladder), and SK-OV-3 (ovarian) human cancer cells. Interestingly, complexes 1–8 showed higher cytotoxicity than cisplatin against human cervical HeLa cells, and less cytotoxicity on the HL-7702 nontumorigenic cells. Mechanism studies suggested that complexes 1 and 2 arrested the cell cycle in the G1 phase and induced cancer cell death through mitochondrial dysfunction pathways. The cytotoxicity of 2 was higher than that of 1. The different biological behavior of 1 and 2 may correlate with the presence of a 2-methyl group in 6,7-dichloro-2-methyl-5,8-quinolinedione (DMQ) ligand. In general, our study demonstrated that Zn(II) complex 2 with 6,7-dichloro- 2-methyl-5,8-quinolinedione showed high potential to be developed as a mitochondria-targeted metal antitumor agent.
Mixed quinoline derivative iridium (III) complex as well as preparation method and application thereof
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Paragraph 0036; 0051-0053; 0058-0060, (2021/04/07)
The invention discloses a mixed quinoline derivative iridium (III) complex as well as a preparation method and application thereof, and belongs to the field of medicines. The chemical name of the compound is hexafluorophosphorylate.pyrido [3, 2-a] pyrido [1 ', 2': 1, 2] imidazo [4, 5-c] phenazine. Dibenzoquinoline iridium (III). The preparation method comprises the following steps: reacting 8hydroxyquinoline with hydrochloric acid and NaClO3; adding anhydrous potassium carbonate; adding 2-aminopyridine; adding o-phenylenediamine; obtaining a compound 3a; reacting 7,8-benzoquinoline with iridium trichloride hydrate to obtain a compound 4; and reacting the compound 3a with the compound 4 to obtain the mixed quinoline derivative iridium (III) complex. The in-vitro anti-tumor activity of the compound on a human ovarian cancer drug-resistant strain SK-OV-3/DDP is greater than that of an 8-hydroxyquinoline derivative ligand and a metal-based anti-cancer drug cis-platinum; the toxicity to normal cells HL-7702 is very low, and a good effect of targeted inhibition of human ovarian cancer proliferation is reflected.
