Discovery of a novel series of substituted quinolines acting as anticancer agents and selective EGFR blocker: Molecular docking study

Kumar, C.B. Pradeep; Raghu, M.S.; Prathibha, B.S.; Prashanth, M.K.; Kanthimathi, G.; Kumar, K. Deva Arun; Parashuram, L.; Alharthi, Fahad A.

doi:10.1016/j.bmcl.2021.128118

Cited by 64 publications

(21 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[15] Metal complexes of ligands containing quinoline moiety have attracted particular interest because of their biological activities. [16][17][18] Semicarbazones display disparate coordination modes with metal ions that are influenced by numerous factors like reaction conditions, nature of the substituent on the carbonyl compound, metal salt, and the nature of counter ions. [19] In addition, semicarbazones are reported to possess versatile structural features and their metal complexes are more biologically active than the free ligands.…”

Section: Introductionmentioning

confidence: 99%

Novel NO₂ semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

Salah

Emara

Adly

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

A novel semicarbazone NO 2 ligand, H 2 L, was synthesized. The ligand reacted with several metal ions such as Cu(II), Ni(II), Co(II), Fe(III), Cr(III), and Mn(II) in a molar ratio 1:1 (M:L). The H 2 L ligand and its metal complexes were characterized by electronic, infrared, mass, nuclear magnetic resonance, electron spin resonance spectra, as well as elemental analysis, thermal analysis, molar conductance, and magnetic susceptibility measurements. The Coats-Redfern equations were used to calculate the kinetic parameters (E a , A, ΔH, ΔS, and ΔG) of the thermal decomposition stages. The H 2 L ligand acts as dianionic NO 2 tridentate in all complexes and coordinates through enolate oxygen, azomethine nitrogen, and deprotonated OH group. The geometrical arrangements in all metal complexes were octahedral geometries. Based on density functional theory (DFT) level implemented in the Gaussian 09 program at B3LYP/6-311G(d,p) level, the molecular structural parameters of the ligand and its metal complexes were calculated, and the theoretical data were connected with the experimental results. The antimicrobial activity of the current compounds was examined against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Salmonella typhimurium and Escherichia coli), yeast (Candida albicans), and fungus (Aspergillus fumigatus). The antitumor activity of the ligand and its metal complexes was investigated against HepG2 cell line, which revealed promising IC 50 values comparable with that of Cis-platin. All synthesized compounds were also subjected to molecular docking studies to investigate their binding pattern and affinity for the VEGFR-2 active site and correlated with antitumor data.

show abstract

Section: Introductionmentioning

confidence: 99%

Novel NO₂ semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

Salah

Emara

Adly

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…The target compounds' abilities to inhibit the EGFR kinase were assessed using 96-well plates and the previously published enzyme-linked immunosorbent assays (ELISA) [ 32 ]. The IC 50 values for each compound's EGFR kinase activity were reported.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, anticancer activity and docking studies of novel quinazoline-based thiazole derivatives as EGFR kinase inhibitors

Raghu,

Swarup,

Shamala

et al. 2023

Heliyon

Self Cite

View full text Add to dashboard Cite

“…Molecular docking studies were carried out using Auto dock tools by taking epidermal growth factor receptor (EGFR) as the target because there are many number of reports related to EGFR inhibition by quinoline, morpholine and 1,2,3‐triazole based hybrid molecules [19a–l] . The protein was downloaded in pdb format (pdb id‐4HJO) from protein data bank [20] .…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

Synthesis of Quinoline‐Morpholine‐Coupled 1,2,3‐Triazole Hybrids as In vitro EGFR inhibitors

Mamidala

Bokkala²,

Thirukovela³

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

Herein we described the synthesis of some new quinolinemorpholine coupled 1,2,3-triazole hybrids (6 a-n) from 5chloroquinolin-8-ol using well known reactions like Mannich reaction, O-propargylation, and finally copper (I) catalyzed azide-alkyne cycloaddition (CuAAC). The structures of all newly synthesized hybrids were confirmed by 1 H-NMR, 13 C-NMR, and Mass spectra. All of them were screened for their in vitro cytotoxicity towards three human cancer cell lines including MCF-7, A549 and HepG2 by MTT assay where four compounds (6 c, 6 j, 6 m and 6 n) exhibited more potency than the reference erlotinib against all the three cell lines. In vitro tyrosine kinase EGFR inhibition assay for the same four compounds revealed that 6 m has triple inhibiting power with IC 50 value of 0.14 μM and 6 j has nearly double inhibiting power with IC 50 value of 0.22 μM compared to erlotinib. Molecular docking studies with EGFR have shown that all the above four compounds have more binding energies (À 9.09 kcal/mol to À 9.96 kcal/mol) than that of erlotinib (-7.69 kcal/mol). Finally, in silico pharmacokinetic profile was achieved using SWISS/ADME and pkCSM, where all the four compounds followed Lipinski rule, Veber rule, Egan rule and Muegge rule and the lipophilicity (ClogP) was found to be ranging from 2.98 to 3.69.

show abstract

Discovery of a novel series of substituted quinolines acting as anticancer agents and selective EGFR blocker: Molecular docking study

Cited by 64 publications

References 48 publications

Novel NO₂ semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

Novel NO₂ semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

Design, synthesis, anticancer activity and docking studies of novel quinazoline-based thiazole derivatives as EGFR kinase inhibitors

Synthesis of Quinoline‐Morpholine‐Coupled 1,2,3‐Triazole Hybrids as In vitro EGFR inhibitors

Contact Info

Product

Resources

About

Discovery of a novel series of substituted quinolines acting as anticancer agents and selective EGFR blocker: Molecular docking study

Cited by 64 publications

References 48 publications

Novel NO2 semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

Novel NO2 semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

Design, synthesis, anticancer activity and docking studies of novel quinazoline-based thiazole derivatives as EGFR kinase inhibitors

Synthesis of Quinoline‐Morpholine‐Coupled 1,2,3‐Triazole Hybrids as In vitro EGFR inhibitors

Contact Info

Product

Resources

About

Novel NO₂ semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation

Novel NO₂ semicarbazone ligand and its metal complexes as VEGFR‐2 inhibitors: Synthesis, spectral characterization, density functional theory calculations, molecular docking, and antimicrobial and antitumor evaluation