4420-46-6Relevant academic research and scientific papers
Cyclometalated cinchophen ligands on iridium(iii): Towards water-soluble complexes with visible luminescence
Smith, Rebecca A.,Stokes, Emily C.,Langdon-Jones, Emily E.,Platts, James A.,Kariuki, Benson M.,Hallett, Andrew J.,Pope, Simon J. A.
, p. 10347 - 10357 (2013)
Eight cationic heteroleptic iridium(iii) complexes, [Ir(epqc) 2(N^N)]+, were prepared in high yield from a cyclometalated iridium bridged-chloride dimer bearing two ethyl-2- phenylquinoline-4-carboxylate (epqc) ligands. Two X-ray cry
Water-soluble, luminescent iridium(iii)-ytterbium(iii) complexes using dipyrido[3,2-a:2′,3′-c]phenazine derivatives as bridging units
Jones, Jennifer E.,Jenkins, Robert L.,Hicks, Robin S.,Hallett, Andrew J.,Pope, Simon J. A.
, p. 10372 - 10381,10 (2012)
Amino-substituted dipyrido[3,2-a:2′,3′-c]phenazine (L 1) and dimethyl-dipyrido[3,2-a:2′,3′-c]phenazine (L 2) have been investigated as: (i) chromophores in cyclen-based ligands for lanthanide(iii) ions; (ii) ancillary co-ligands in c
Palladium-Catalyzed Three-Component Cascade Reaction of Nitriles: Synthesis of 2-Arylquinoline-4-carboxylates
Zhao, Zhiwei,Zeng, Ge,Chen, Yinan,Zheng, Jinming,Chen, Zhongyan,Shao, Yinlin,Zhang, Fangjun,Chen, Jiuxi,Li, Renhao
, p. 7955 - 7960 (2021/10/20)
A new method for converting easy availability starting materials 2-(2-oxoindolin-3-yl)acetonitrile, arylboronic acids, and alcohols into 2-arylquinoline-4-carboxylates is reported. The procedure involves a three-component addition/ring expansion/esterification reaction in the presence of Pd(II) catalyst with high functional group tolerance under mild conditions. In addition, the photophysical properties of the resulting product were investigated and exhibited excellent polarity-sensitive fluorescence properties and AIE property.
Design and synthesis of novel quinoline/chalcone/1,2,4-triazole hybrids as potent antiproliferative agent targeting EGFR and BRAFV600E kinases
Mohassab, Aliaa M.,Hassan, Heba A.,Abdelhamid, Dalia,Gouda, Ahmed M.,Youssif, Bahaa G.M.,Tateishi, Hiroshi,Fujita, Mikako,Otsuka, Masami,Abdel-Aziz, Mohamed
, (2020/12/07)
New quinoline / chalcone hybrids containing 1,2,4-triazole moiety have been designed, synthesized and their structures elucidated and confirmed by various spectroscopic techniques. The designed compounds showed moderate to good activity on different NCI 60 cell lines in a single-dose assay with a growth inhibition rate ranging from 50% to 94%. Compounds 7b, 7d, 9b, and 9d were the most active compounds in most cancer cell lines with a growth inhibition percent between 77% and 94%. Newly synthesized hybrids were evaluated for their anti-proliferative activity against a panel of four human cancer cell lines. Compounds 7a, 7b, 9a, 9b, and 9d showed promising antiproliferative activities. These compounds were further tested for their inhibitory potency against EGFR and BRAFV600E kinases with erlotinib as a reference drug. The molecular docking study of compounds 7a, 7b, 9a, 9b, and 9d revealed nice fitting into the active site of EGFR and BRAFV600E kinases. Compounds 7b, 9b, and 9d displayed the highest binding affinities and similar binding pattern to those of erlotinib.
New quinoline/1,2,4-triazole hybrids as dual inhibitors of COX-2/5-LOX and inflammatory cytokines: Design, synthesis, and docking study
Abdel-Aziz, Mohamed,Abdelhamid, Dalia,Fujita, Mikako,Gomaa, Hesham A. M.,Gouda, Ahmed M.,Hassan, Heba A.,Mohassab, Aliaa M.,Otsuka, Masami,Radwan, Mohamed O.,Youssif, Bahaa G. M.
, (2021/07/06)
A novel series of 19 quinoline/1,2,4-triazole hybrid 6a-i and 7a-j was synthesized and evaluated in vitro as dual COX-2/5-LOX inhibitors. Compounds 6e, 6i, and 7e displayed the highest potency and selectivity for inhibiting COX-2 activity (IC50 = 7.25, 8.13, and 8.48 nM, respectively; selectivity index (COX-1/COX-2) = 44.89, 30.30, and 33.47, respectively) in comparison to celecoxib (COX-2 IC50 = 42.60 nM; selectivity index (SI) = 8.05). The anti-inflammatory activity of the newly synthesized compounds was further examined in vivo using a carrageenan induced paw edema assay. Interestingly, the in vitro findings of the COX inhibitory assay were consistent with the in vivo assay. Moreover, 6e, 6i, and 7e showed a substantial reduction in serum concentrations of PGE2, TNF-α, IL-6. Molecular docking analysis of compounds 6e, 6f, 6i, 7e, and 7f revealed high binding affinities toward COX-2 compared to COX-1, which was matched with the experimental results. In addition, these compounds exhibited different binding orientations into the active site of COX-2, which were dependent on the type of substitutions on N4 of the triazole ring. Among the tested derivatives, compounds 6e, 6i and 7e which showed high selectivity to COX-2, exhibited hydrogen bonding interactions with key amino acids in COX-2 such as Arg120, Arg513, and/or Glu524. In addition, the tested compounds also showed multiple hydrogen bonds with the Arg101, Val110, Arg138 or His130 in 5-LOX. These findings show, taken together, that those derivatives are good leads to potential anti-inflammatory agents with lowest gastric damage.
Ethyl lactate-involved three-component dehydrogenative reactions: Biomass feedstock in diversity-oriented quinoline synthesis
Wan, Jie-Ping,Yang, Lu
, p. 3074 - 3078 (2020/06/25)
Three-component reactions of ethyl/methyl lactate, anilines and aldehydes providing quinolines have been developed via simple iron(iii) chloride catalysis without using an additional organic medium or external oxidant. This three-component protocol shows
NO-releasing STAT3 inhibitors suppress BRAF-mutant melanoma growth
Kaoud, Tamer S.,Mohassab, Aliaa M.,Hassan, Heba A.,Yan, Chunli,Van Ravenstein, Sabrina X.,Abdelhamid, Dalia,Dalby, Kevin N.,Abdel-Aziz, Mohamed
, (2019/12/09)
Constitutive activation of STAT3 can play a vital role in the development of melanoma. STAT3-targeted therapeutics are reported to show efficacy in melanomas harboring the BRAFV600E mutant and also in vemurafenib-resistant melanomas. We designed and synthesized a series of substituted nitric oxide (NO)-releasing quinolone-1,2,4-triazole/oxime hybrids, hypothesizing that the introduction of a STAT3 binding scaffold would augment their cytotoxicity. All the hybrids tested showed a comparable level of in vitro NO production. 7b and 7c exhibited direct binding to the STAT3-SH domain with IC50 of ～ 0.5 μM. Also, they abrogated STAT3 tyrosine phosphorylation in several cancer cell lines, including the A375 melanoma cell line that carries the BRAFV600E mutation. At the same time, they did not affect the phosphorylation of upstream kinases or other STAT isoforms. 7c inhibited STAT3 nuclear translocation in mouse embryonic fibroblast while 7b and 7c inhibited STAT3 DNA-binding activity in the A375 cell line. Their anti-proliferating activity is attributed to their ability to trigger the production of reactive oxygen species and induce G1 cell cycle arrest in the A375 cell line. Interestingly, 7b and 7c showed robust cell growth suppression and apoptosis induction in two pairs of BRAF inhibitor-na?ve (-S) and resistant (-R) melanoma cell lines containing a BRAF V600E mutation. Surprisingly, MEL1617-R cells that are known to be more resistance to MEK inhibition by GSK1120212 than MEL1617-S cells exhibit a similar response to 7b and 7c.
New quinoline/chalcone hybrids as anti-cancer agents: Design, synthesis, and evaluations of cytotoxicity and PI3K inhibitory activity
Abbas, Samar H.,Abd El-Hafeez, Amer Ali,Shoman, Mai E.,Montano, Monica M.,Hassan, Heba A.
supporting information, p. 360 - 377 (2018/11/23)
A series of quinoline-chalcone hybrids was designed as potential anti-cancer agents, synthesized and evaluated. Different cytotoxic assays revealed that compounds experienced promising activity. Compounds 9i and 9j were the most potent against all the cell lines tested with IC50 = 1.91–5.29 μM against A549 and K-562 cells. Mechanistically, 9i and 9j induced G2/M cell cycle arrest and apoptosis in both A549 and K562 cells. Moreover, all PI3K isoforms were inhibited non selectively with IC50s of 52–473 nM when tested against the two mentioned compounds with 9i being most potent against PI3K-γ (IC50 = 52 nM). Docking of 9i and 9j showed a possible formation of H-bonding with essential valine residues in the active site of PI3K-γ isoform. Meanwhile, Western blotting analysis revealed that 9i and 9j inhibited the phosphorylation of PI3K, Akt, mTOR, as well as GSK-3β in both A549 and K562 cells, suggesting the correlation of blocking PI3K/Akt/mTOR pathway with the above antitumor activities. Together, our findings support the antitumor potential of quinoline-chalcone derivatives for NSCLC and CML by inhibiting the PI3K/Akt/mTOR pathway.
Synthesis and Anticonvulsant Potential of Some New 4-[5-substituted-[1,3,4] oxadiazole-2-yl]-2-phenylquinolines
Abdullah, Mohammad Mustqeem,Kumar, Rajnish
, p. 79 - 86 (2021/06/12)
A new series of 4-[5-substituted-[1, 3, 4] oxadiazole-2-yl]-2-phenylquinolines was synthesized and evaluated for their anticonvulsant potential using minimal electroshock and subcutaneous pentylenetetrazole animal model methods. The structures of compounds were elucidated by elemental analysis (C, H, N) and spectral data (infrared,1H nuclear magnetic resonance, and Mass). Locomotor behavior of compounds was evaluated by actophotometer, and toxicology study was also performed to evaluate their significance as required anticonvulsant compounds.
Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles
Verbanac, Donatella,Malik, Ritu,Chand, Mahesh,Kushwaha, Khushbu,Vashist, Monika,Matija?i?, Mario,Stepani?, Vi?nja,Peri?, Mihaela,Paljetak, Hana ?ip?i?,Saso, Luciano,Jain, Subhash C.
, p. 104 - 110 (2016/12/14)
A set of novel quinolone–triazole conjugates (12–31) were synthesized in three steps in good yields starting from 2-phenylquinoline-4-carboxylic acid. All the intermediates, as well as the final 1,2,4-triazolyl quinolines were fully characterized by their detailed spectral analysis utilizing different techniques such as IR, 1H NMR, 13C NMR, and finally mass spectrometry. All the synthesized compounds were evaluated in vitro for their potential antibacterial activity and their preliminary safety profile was assessed through cytotoxicity assay. Additionally, six selected conjugates were evaluated for their antioxidative properties on the basis of density functional theory calculations, using radical scavenging assay (DPPH) and cellular antioxidant assay. The reported results encourage further investigation of selected compounds and are shading light on their potential pharmacological use.
