73568-41-9Relevant articles and documents
Synthesis, crystal structure, anticancer and molecular docking studies of quinolinone-thiazolidinone hybrid molecules
Kumar, Vasantha,Rai, Vaishali M.,Udupi, Vishwanatha,Shivalingegowda, Naveen,Pai, Vinitha R.,Krishnappagowda, Lokanath Neratur,Poojary, Boja
, p. 793 - 808 (2021/08/12)
A new series of quinolone-thiazolidinone hybrid molecules 8a-o were prepared. Quinoline compounds were synthesized by Meth-Cohn synthesis and were condensed with 2,3-disubstituted thiazolidinone. These molecules were screened for their anticancer activities against MDA-MB-231 and MCF-7 cell line using MTT assay. Potent compounds were tested for their cytotoxicity on normal HEK 293 cell lines and most potent compound was tested for its cell cycle analysis. Molecular docking and molecular dynamic studies were performed on human N-acetyl transferase (hNAT-1) protein using Schrodinger molecular docking toolkit. Compound 8n emerged as potent with IC50 8.16?μM against MDA-MB-231 cell line followed by 8e with IC50 17.68?μM. Compound 8n arrested cell cycle at G2/M phase and was non-toxic to human normal kidney cell line. The potent compound 8n binds well with human NAT-1 protein with remarkable hydrogen bonding and π–π interactions. Molecular dynamic studies of 8n further confirm the target for these molecules. Target quinolinone-thiazolidinones were found to be new class of compounds targeting hNAT-1 and can serve as new lead compounds in drug discovery.
Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents
Bokosi, Fostino R.B.,Beteck, Richard M.,Mbaba, Mziyanda,Mtshare, Thanduxolo E.,Laming, Dustin,Hoppe, Heinrich C.,Khanye, Setshaba D.
, (2021/03/01)
Several classes of antimalarial drugs are currently available, although issues of toxicity and the emergence of drug resistant malaria parasites have reduced their overall therapeutic efficiency. Quinoline based antiplasmodial drugs have unequivocally been long-established and continue to inspire the design of new antimalarial agents. Herein, a series of mono- and bisquinoline methanamine derivatives were synthesised through sequential steps; Vilsmeier-Haack, reductive amination, and nucleophilic substitution, and obtained in low to excellent yields. The resulting compounds were investigated for in vitro antiplasmodial activity against the 3D7 chloroquine-sensitive strain of Plasmodium falciparum, and compounds 40 and 59 emerged as the most promising with IC50 values of 0.23 and 0.93 μM, respectively. The most promising compounds were also evaluated in silico by molecular docking protocols for binding affinity to the {0 0 1} fast-growing face of a hemozoin crystal model.
Design, synthesis, and molecular docking study of novel quinoline-based bis-chalcones as potential antitumor agents
Insuasty, Daniel,García, Stephanie,Abonia, Rodrigo,Insuasty, Braulio,Quiroga, Jairo,Nogueras, Manuel,Cobo, Justo,Borosky, Gabriela L.,Laali, Kenneth K.
, (2021/06/01)
A novel series of quinoline-based symmetrical and unsymmetrical bis-chalcones was synthesized via a Claisen–Schmidt condensation reaction between 3-formyl-quinoline/quinolone derivatives with acetone or arylidene acetones, respectively, by using KOH/MeOH/H2O as a reaction medium. Twelve of the obtained compounds were evaluated for their in vitro cytotoxic activity against 60 different human cancer cell lines according to the National Cancer Institute protocol. Among the screened compounds, the symmetrical N-butyl bis-quinolinyl-chalcone 14g and the unsymmetrical quinolinyl-bis-chalcone 17o bearing a 7-chloro-substitution on the N-benzylquinoline moiety and 4-hydroxy-3-methoxy substituent on the phenyl ring, respectively, exhibited the highest overall cytotoxicity against the evaluated cell lines with a GI50 range of 0.16–5.45 μM, with HCT-116 (GI50 = 0.16) and HT29 (GI50 = 0.42 μM) (colon cancer) representing best-case scenarios. Notably, several GI50 values for these compounds were lower than those of the reference drugs doxorubicin and 5-FU. Docking studies performed on selected derivatives yielded very good binding energies in the active site of proteins that participate in key carcinogenic pathways.
Synthesis and characterization of biologically important quinoline incorporated triazole derivatives
D'Souza, Vineetha Telma,Nayak, Janardhana,D'Mello, Desmond Edward,Dayananda
, (2020/11/04)
Triazoles are well recognized in literature for their significant biologically active heterocyclic compounds. Also the quinoline nucleus found in several natural products shows a varied biological activity. Keeping in the view of these observations, a novel series of 6/7/8-substtuted-2-[(5-((4-chlorophenoxy)methyl)-4H-1,2,4-triazol-3-yl)thio]quinoline-3-carbaldehydes and 6/7/8-substituted-2-[(5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio]quinoline-carbaldehydes were synthesized by the condensation of 5-(4-chloro phenoxy methyl)-2,4-dihydro-1,2,4-triazole-3-thiones and 5-(pyridin-3-yl)-4H-1,2,4-triazole-3-thiols with 6/7/8-substituted-2-chloro quinoline-3-carbaldehydes. The new series were established by Mass, NMR and IR spectroscopy and were also screened for their antimicrobial activities. A few of the novel compounds exhibited tremendous bioactivities compared to that of normal drug.
Microwave assisted regioselective synthesis of quinoline appended triazoles as potent anti-tubercular and antifungal agents via copper (I) catalyzed cycloaddition
Nesaragi, Aravind R.,Kamble, Ravindra R.,Bayannavar, Praveen K.,Shaikh, Saba Kauser J.,Hoolageri, Swati R.,Kodasi, Barnabas,Joshi, Shrinivas D.,Kumbar, Vijay M.
supporting information, (2021/04/12)
Quinolin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4H)-ones 8j-v were synthesized by click chemistry as an ultimate tactic where [3 + 2] cycloaddition of azides with terminal alkynes has been evolved. Herein, we are inclined to divulge the implication and prevalence of CuSO4·5H2O and THF/water promoted [3 + 2] cycloaddition reactions. The foremost supremacy of this method are transitory reaction times, facile workup, excellent yields (88–92%) with exorbitant purity and regioselective single product formation both under conventional and microwave method. Docking studies illustrated strong binding interactions with enzyme InhA-D148G (PDB ID: 4DQU) by means of high C-score values. The anti-tubercular and antifungal screening of synthesized compounds proclaimed promising activity. The in vitro and in silico studies imply that these triazoles appended quinolines may acquire the ideal structural prerequisites for auxiliary expansion of novel therapeutic agents.
Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-: B] quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones
Li, Jingyi,Ling, Fei,Lu, Yin-Jie,Shao, Bingxuan,Xiao, Xiao,Yang, Zehui,Zhong, Weihui
supporting information, p. 4690 - 4693 (2021/05/19)
An enantioselective synthesis of highly functionalized 1,4-dihydropyrazolo[4′,3′:5,6]pyrano[2,3-b]quinolines from modified MBH carbonates and pyrazolones via a chiral phosphine-mediated alkylation/annulation sequence has been realized. The chiral dihydropyrano[2,3-c]pyrazoles bearing bio-active condensed heterocycles were facilely formed in good chemical yields and with high to excellent enantioselectivity by utilizing low catalyst loading.
Synthesis, in silico Molecular Docking and Antimicrobial Study of Some New 3-(Substituted-quinolin-3-yl)-1-[4-(1H-pyrrol-1-yl)phenyl]prop-2-en-1-one Derivatives
Almehizia, Abdulrahman A.,Alshabi, Ali Mohamed,Joshi, Shrinivas D.,Kulkarni, Venkatarao H.,Kumar, R. Prem,Shaikh, Ibrahim Ahmed
, p. 91 - 100 (2021/08/12)
New series of 3-(substituted-2-chloroquinolin-3-yl)-1-(4-(1H-pyrrol-1-yl)phenyl)prop-2-en-1-ones 4(a-e)/3-(substituted-2-methoxyquinolin-3-yl)-1-(4-(1H-pyrrol-1-yl)phenyl)prop-2-en-1-ones 6(a-e) were synthesized by base catalyzed reaction/chalcone synthes
Synthesis and antimicrobial activities of thiadiazole containing quinoline derivatives
Dayananda,Nayak, Janardhana,D'Souza, Vineetha Telma
, p. 633 - 638 (2021/09/28)
A novel series of 1-[(substituted 2-chloroquinolin-3-yl)methylidene]-3-[substituted-5-phenyl-1,3,4-thiadiazol-2-yl] thioureas have been synthesized by acid catalyzed reaction between the 1-(5-substitued phenyl-1,3,4-thiadiazol-2-yl) thioureas and 6-substi
Synthesis, photophysical properties and theoretical studies of new bis-quinolin curcuminoid BF2-complexes and their decomplexed derivatives
Abonia, Rodrigo,Cabrera, Lorena,Insuasty, Braulio,Insuasty, Daniel,Ortiz, Alejandro,Quiroga, Jairo
, (2020/01/21)
This paper presents the synthesis and characterization of two series of new bis-quinolin curcuminoid BF2-complexes 11 and their respective decomplexed bis-quinolin curcuminoid derivatives 12, in an attempt to understand their optical properties. The synthesized compounds showed interesting fluorescent characteristics in both solution and in solid-state. The characteristic of the electronic transitions involved in these systems were measured via Uv-vis spectroscopy and fluorescence spectroscopy. Results revealed that the absorption and emission bands are dependent of the structure of compounds 11 and 12 but also of the type of substituent, even showing a push-pull behavior in those derivatives substituted with methyl group. These findings were also confirmed through computational calculations at DFT level via simulations of the Uv-vis spectra and determining the topology of the border orbitals responsible for light absorption.
Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones
Govender, Hogantharanni,Mocktar, Chunderika,Kumalo, Hezekiel M.,Koorbanally, Neil A.
, p. 1074 - 1081 (2019/06/10)
Fifteen 2-quinolone thiosemicarbazone derivatives of which eleven were new, were synthesized at room temperature. The key intermediate was the quinolone carbaldehyde, from which thiosemicarbazones were formed by the reaction of thiosemicarbazides with the aldehyde moiety. The structures of the synthesized compounds were elucidated by 1D and 2D-NMR spectroscopy and mass spectrometry. The synthesized compounds showed antibacterial activity with MBCs in the range 0.80 to 36.49 mM against Staphylococcus aureus, Staphylococcus aureus Rosenbach (MRSA), Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli and Salmonella typhimurium. The best activity was seen when a larger halogen such as chlorine and bromine were substituted at C-6 on the quinolone scaffold and when a planar phenyl group was present on the thiosemicarbazone moiety. Activity was reduced when a smaller fluorine atom was present at C-6 or when a methyl group was attached to the thiosemicarbazone. This group of compounds showed a high negative binding affinity, which suggested promising antimcrobial activity. The 6-chloro derivative with a phenyl group on the thiosemicarbazone had the greatest negative binding affinity.
