91301-03-0Relevant articles and documents
Spectroscopy, electrochemistry, and structure of 3d-transition metal complexes of thiosemicarbazones with quinoline core: Evaluation of antimicrobial property
Kulkarni, Naveen V.,Hegde, Ganesh S.,Kurdekar, Gurunath S.,Budagumpi, Srinivasa,Sathisha,Revankar, Vidyanand K.
, p. 235 - 246 (2010)
A series of Co(II), Ni(II), Cu(II), and Zn(II) complexes of quinoline-thiosemicarbazones was prepared. The Schiff base ligands that provide N, O, and S donor atoms for ligation are synthesized by the condensation of 2-hydroxy-3-formylquinoline with substituted thiosemicarbazides in ethanol. The ligands and complexes are characterized by elemental analysis, infrared, 1H NMR, UV-Vis, fast atom bombardment (FAB) mass spectroscopy, and electron spin resonance (ESR) spectral studies followed by magnetic susceptibility and conductivity measurements. The ligand-to-metal ratio is found to be 1:1 and 2:2 for the complexes of L1H2 and LcH2, respectively. All the complexes are found to have octahedral geometry except [CuL1H(H2O)Cl], which exhibits a square pyramidal structure. All the complexes are nonelectrolytic in nature and the electrochemical behavior of complexes is dealt with briefly. Further ligands and complexes were evaluated for their antimicrobial activity against bacteria Escherichia coli and Pseudomonas aeruginosa and fungi Aspergillus niger and Cladosporidium. Taylor & Francis Group, LLC.
A highly selective chemosensor for Al3+ based on 2-oxo-quinoline-3-carbaldehyde Schiff-base
Zhang, Ke,Yang, Zheng-Yin,Wang, Bao-Dui,Sun, Shao-Bo,Li, Ying-Dong,Li, Tian-Rong,Liu, Zeng-Chen,An, Jun-Mei
, p. 59 - 63 (2014)
A new Schiff-base ligand (1) with good fluorescence response to Al 3+, derived from 2-oxo-quinoline-3-carbaldehyde and nicotinic hydrazide, had been synthesized and investigated in this paper. Spectroscopic investigation revealed that the compound 1 exhibited a high selectivity and sensitivity toward Al(III) ions over other commonly coexisting metal ions in ethanol, and the detection limit of Al3+ ions is at the parts per billion level. The mass spectra and Job's plot confirmed the 1:1 stoichiometry between 1 and Al3+. Potential utilization of 1 as intracellular sensors of Al3+ ions in human cancer (HeLa) cells was also examined by confocal fluorescence microscopy.
Design, synthesis, and evaluation of new 2-oxoquinoline arylaminothiazole derivatives as potential anticancer agents
Fang, Yilin,Wu, Zhilin,Xiao, Mengwu,Wei, Li,Li, Kangming,Tang, Yuting,Ye, Jiao,Xiang, Jiannan,Hu, Aixi
, (2021)
A series of novel 2-oxoquinoline derivatives containing arylaminothiazole were designed and synthesized as potential antitumor agents. The synthesized compounds were evaluated for their in vitro cytotoxicity activity against HeLa, NCI-H460, T24 and SKOV3
A Schiff's base receptor for red fluorescence live cell imaging of Zn2+ ions in zebrafish embryos and naked eye detection of Ni2+ ions for bio-Analytical applications
Senthil Murugan,Vidhyalakshmi,Ramesh,Annaraj
, p. 3195 - 3200 (2017)
An interesting dual chemoreceptor (QAMP) was synthesized to quantify the presence of two environmentally as well as biologically important Zn2+/Ni2+ ions in a highly selective manner using different analytical techniques. The fluorescence profile was enhanced to 663 nm (red region) due to the formation of its 1 : 1 complex with Zn2+ at room temperature even in the presence of other interfering ions such as Cd2+ and Hg2+. Moreover, it exhibits excellent chromo-isomerism with Ni2+ ions. Meanwhile, this assay could be successfully oriented with molecular logic functions of AND, OR, NOR and NOT logic gates. The obtained large Stokes shift (～274 nm) value and red emission promoted this receptor as a potential tool for biological studies (e.g. live cell imaging in cancer cell line and zebrafish models).
Synthesis and photophysical investigation of 2-hydroxyquinoline-3-carbaldehyde: AIEE phenomenon, fluoride optical sensing and BSA interaction study
Chakraborty, Nilanjan,Bhuiya, Sutanwi,Chakraborty, Arijit,Mandal, Deep,Das, Suman
, p. 53 - 63 (2018)
Nowadays compounds showing aggregation-induced emission enhancement (AIEE) are extensively studied due to their huge range of applications in material science. AIEE and the anion recognition ability of 2-hydroxyquinoline-3-carbaldehyde (1) were explored. Unique AIEE phenomenon is observed in CH3CN with water as the cosolvent and the highest emission was noted in the solvent volume ratio 2:8 (CH3CN: H2O). The compound is a selective time dependent turn on fluoride ion sensor in acetonitrile medium with a distinct color change from colorless to yellow, fabricating it as a visible sensor. Ion sensing ability was monitored through UV–vis, steady state emission, life time studies and 1H NMR spectroscopy. The limit of detection of fluoride ion is 4.09 × 10?6 M. Moreover the compound exhibited notable quenching of fluorescence intensity with bovine serum albumin. Thus small molecule like the quinoline motif can be used in extensive applications in the scientific research.
Chemistry of mixed-ligand oxidovanadium(IV) complexes of aroylhydrazones incorporating quinoline derivatives: Study of solution behavior, theoretical evaluation and protein/DNA interaction
Banerjee,Dash, Subhashree P.,Mohanty, Monalisa,Sanna, Daniele,Sciortino, Giuseppe,Ugone, Valeria,Garribba, Eugenio,Reuter, Hans,Kaminsky, Werner,Dinda
, (2019)
A series of eight hexacoordinated mixed-ligand oxidovanadium(IV) complexes [VO(Lx)(LN-N)] (1–8), where Lx = L1 – L4 are four differently substituted ONO donor aroylhydrazone ligands and LN-N are N,N-donor bases like 2,2′-bipyridine (bipy) (1, 3, 5 and 7) and 1,10-phenanthroline (phen) (2, 4, 6 and 8), have been reported. All synthesized complexes have been characterized by various physicochemical techniques and molecular structures of 1 and 6 were determined by X–ray crystallography. With a view to evaluate the biological activity of the VIVO species, the behavior of the systems VIVO2+/Lx, VIVO2+/Lx/bipy and VIVO2+/Lx/phen was studied as a function of pH in a mixture of H2O/DMSO 50/50 (v/v). DFT calculations allowed finding out the relative stability of the tautomeric forms of the ligands, and predicting the structure of vanadium complexes and their EPR parameters. To study their interaction with proteins, firstly the ternary systems VIVO2+/L1,2 with 1-methylimidazole, which is a good model for histidine binding, were examined. Subsequently the interaction of the complexes with lysozyme (Lyz), cytochrome c (Cyt) and bovine serum albumin (BSA) was studied. The results indicate that the complexes showed moderate binding affinity towards BSA, while no interaction takes place with lysozyme and cytochrome c. This could be explained with the higher number of accessible coordinating and polar residues for BSA than for Lyz and Cyt. Further, the complexes were also evaluated for their DNA binding propensity through UV–vis absorption titration and fluorescence spectral studies. These results were consistent with BSA binding affinity and showed moderate binding affinity towards CT-DNA.
Efficient synthesis of some pyrimidine and thiazolidine derivatives bearing quinoline scaffold under microwave irradiation
El-Naggar, Abeer M.,Ramadan, Sayed K.
, p. 2188 - 2198 (2020)
An efficient and facile approach for the synthesis of new quinoline derivatives was accomplished via reactions of 2-chloroquinoline-3-carbaldehyde with active methylene compounds, for example, 1,3-dimethylbarbituric acid, thiobarbituric acid and 2,4-dioxo
Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties
Boukhari, Abbes,Djahoudi, Abdelghani,Litim, Bilal,Meliani, Saida
, p. 60 - 74 (2021/11/09)
To develop novel antimicrobial agents, and based on the biologically active heterocyclic quinoline and thiazole substituted, a series of novel α-aminophosphonates (9a–h) and (10i–l) derivatives that incorporated quinoline or quinolone, and coumarylthiazole or 5-phenylthiazol-2-amine moieties were designed and synthesized via Kabachnik–Fields reaction in the presence of ionic liquid under ultrasound irradiation. All the new compounds were obtained in good yield with a simple workup and were confirmed using various spectroscopic methods. The in vitro antimicrobial activity of all synthesized compounds were screened in terms of MIC values against the selected strains of Gram-negative and Gram-positive bacteria and two fungal strains using the broth micro-dilution method. The results showed that most of the tested compounds showed moderate inhibitory activities against both Gram‐positive and ‐negative bacteria compared with reference drugs. The following compounds 9e, 9g, 9h, 9i and 9f, 9g, 9h, 10k, 10l are the most active against Gram-positive and Gram-negative bacteria strains, respectively, with MIC values ranging between 0.25 and 128 μg/mL. The synthesized compounds 9b, 9c, 9f, 9g, 9h, 10k, and 10l exhibited excellent antifungal inhibition with MIC values ranging between 0.25 and 32 μg/mL. Structure–activity relationship revealed that the presence of coumarylthiazole moiety and hydroxyl in the quinoline group increased the inhibitory activity against microbial strains pathogens. These results confirm that the synthesized compounds can be potential antimicrobial drugs candidate. [Figure not available: see fulltext.]
New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents
Gaikwad, Nikhil B.,Bansode, Sapana,Biradar, Shankar,Ban, Mayuri,Srinivas, Nanduri,Godugu, Chandraiah,Yaddanapudi, Venkata M.
, (2021/08/07)
A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.
Potential antibacterial and antifungal activities of novel sulfamidophosphonate derivatives bearing the quinoline or quinolone moiety
Bazine, Ismahene,Bendjedid, Samira,Boukhari, Abbes
, (2020/12/09)
A series of new α-sulfamidophosphonate/sulfonamidophosphonate (4a–n) and cyclosulfamidophosphonate (5a–d) derivatives containing the quinoline or quinolone moiety was designed and synthesized via Kabachnik–Fields reaction in the presence of ionic liquid under ultrasound irradiation. This efficient methodology provides new 1,2,5-thiadiazolidine-1,1-dioxide derivatives 5a–d in one step and optimal conditions. The molecular structures of the novel compounds 4a–n and 5a–d were confirmed using various spectroscopic methods. All these compounds were evaluated for their in vitro antibacterial activity against Gram-negative (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853) and Gram-positive (Staphylococcus aureus ATCC 27923) bacteria, in addition to three clinical strains (E. coli 1, P. aeruginosa 1, and S. aureus 1). Most of the tested compounds showed more potent inhibitory activities against both Gram-positive and -negative bacteria compared with the sulfamethoxazole reference. The following compounds, 4n, 4f, 4g, 4m, 4l, 4d, and 4e, are the most active sulfamidophosphonate derivatives. Furthermore, these molecules gave interesting zones of inhibition varying between 28 and 49 mm, against all tested bacterial strains, with a low minimum inhibitory concentration (MIC) value ranging from 0.125 to 8 μg/ml. All the synthesized derivatives were also evaluated for their in vitro antifungal activity against Fusarium oxyporum f. sp. lycopersici and Alternaria sp. The results revealed that all the synthesized compounds exhibited excellent antifungal inhibition and the compounds 4f, 4g, 4m, and 4i were the most potent derivatives with MIC values ranging from 0.25 to 1 μg/ml against the two tested fungal strains. The strongest inhibition of bacteria and fungi strains was detected by the effect of quinolone and sulfamide moieties.
