Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies

Shaikh, Saba Kauser J.; Kamble, Ravindra R.; Bayannavar, Praveen K.; Somagond, Shilpa M.; Joshi, Shrinivas D.

doi:10.1016/j.molstruc.2019.127445

Cited by 9 publications

(3 citation statements)

References 25 publications

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“…The quinoline derivatives were fused with 2-mercaptopyridine-appended triazolothiadiazepine pharmacophore affording a series of triazolothiadizepinylquinolines. [75] The in vitro anticancer screening was performed on the synthesized quinoline derivatives wherein moderate to weak growth inhibitory properties are observed. Particularly, triazolothiadiazepine derivative 29 ( Figure 3) fused with 6-methylquinoline is responsible for decent UO-31 growth inhibitory activity (35.71 %).…”

Section: Fused-quinoline Derivativesmentioning

confidence: 99%

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Report on Recently (2017–20) Designed Quinoline‐Based Human Cancer Cell Growth Inhibitors

Dorababu¹

2020

ChemistrySelect

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Quinoline has been a most essential pharmacophore, derivatization of which led to enticing pharmacological properties. Quinoline is responsible for a wide range of biological potencies such as antibacterial, antifungal, anti-leishmanial, antimalarial, antioxidant and anticancer properties. Out of these clinical importances, the anticancer property of heterocycles is of greatest concern as cancer has become a major threat globally. Since some natural products containing quinoline moiety have displayed cancer inhibition potency, quinoline has been given highest priority in the anticancer drug design and development. In addition, quinoline has got eight positions including nitrogen for substitution which may result in some potential anticancer properties. Ever since, this extraordinary potential is being utilized in anticancer drug discovery. In this review, the various trends in drug design of quinoline moiety anticipating finest anticancer properties through cancer cell growth inhibition are collated comprehensively. The review work is classified based on type of quinoline derivatives. Besides this, with the aid of structure-activity relationship discussion, the importance of structural units that contributed to strongest activity towards cancer inhibition is emphasized. The particular activity would help to bring further advanced anticancer agents in the future.

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Section: Fused-quinoline Derivativesmentioning

confidence: 99%

“…Chemical structures of fused-quinoline derivatives. [72,74,75] electron-withdrawing and electron-donating mono substituted phenyl moieties are responsible for moderate to poor activity. The styrylquinoline moiety 33 ( Figure 4) appended with thiadiazole at quinoline 4-position is active against growth of liver cancer cell line HepG2 (9.0 μg/mL).…”

Section: Compdmentioning

confidence: 99%

Report on Recently (2017–20) Designed Quinoline‐Based Human Cancer Cell Growth Inhibitors

Dorababu¹

2020

ChemistrySelect

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“…The development of new therapeutic anticorona agents made so far has also been limited [ 4 , 5 ]. Heterocyclic compounds such as triazole, thiazole, pyrrole, pyridine, quinolone, etc., and their derivatives are characterized as important classes of organic compounds that exhibit various biological and medicinal properties such as antitumor [ 6 , 7 ], EGFR inhibitory [8] , antioxidant [ 9 , 10 ], antianalgesic, antiinflammatory [11] , antibacterial [12] , antifungal [13] , antimicrobial [14] , etc . The biological properties of many nitrogen based heterocyclic compounds such as triazole and its derivatives have been investigated [15] .…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of heterocyclic azole based bioactive compounds: Molecular structures, quantum simulation, and mechanistic studies through docking as multi-target inhibitors of SARS-CoV-2 and cytotoxicity

Haribabu

Garisetti

Malekshah

et al. 2022

Journal of Molecular Structure

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Two heterocyclic azole compounds, 3-(2,3-dihydrobenzo[d]thiazol-2-yl)-4H-chromen-4-one ( SVS1 ) and 5-(1H-indol-3-yl)-4-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thione ( SVS2 ) were obtained unexpectedly from 2-aminothiophenol and 4-oxo-4H-chromene-3-carbaldehyde (for SVS1 ), and ( E )-2-((1H-indol-3-yl)methylene)-N-methylhydrazine-1-carbothioamide in the presence of anhydrous FeCl 3 (for SVS2 ), respectively. The compounds were well characterized by analytical and spectroscopic tools. The molecular structures of both the compounds were determined by single crystal X-ray diffraction (X-RD) study. The results obtained from density functional theory (DFT) study revealed the molecular geometry and electron distribution of the compounds, which were correlated well with the three-dimensional structures obtained from the single crystal X-ray diffraction. DMol 3 was used to calculate quantum chemical parameters [chemical potential ( µ ), global hardness ( η ), global softness ( σ ), absolute electronegativity ( χ ) and electrophilicity index ( ω )] of SVS1 and SVS2 . Molecular docking study was performed to elucidate the binding ability of SVS1 and SVS2 with SARS-CoV-2 main protease and human angiotensin-converting enzyme-2 (ACE-2) molecular targets. Interestingly, the binding efficiency of the compounds with the molecular targets was comparable with that of remdesivir (SARS-CoV-2), chloroquine and hydroxychloroquine. SVS1 showed better docking energy than SVS2 . The molecular docking study was complemented by molecular dynamic simulation study of SARS-CoV-2 main protease- SVS1 complex, which further exemplified the binding ability of SVS1 with the target. In addition, SVS1, SVS2 and cisplatin were assessed for their cytotoxicity against a panel of three human cancer cells such as HepG-2 (hepatic carcinoma), T24 (bladder) and EA.hy926 (endothelial), as well as Vero (kidney epithelial cells extracted from an African green monkey) normal cells using MTT assay. The results showed that SVS2 has significant cytotoxicity against HepG-2 and EA.hy926 cells with the IC 50 values of 33.8 μM (IC 50 = 49.9 μM-cisplatin and 8.6 μM-doxorubicin) and 29.2 (IC 50 = 26.6 μM-cisplatin and 3.8 μM-doxorubicin), respectively.

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Microwave‐ and Ultrasonic‐Assisted Coupling Reactions

Yadav,

Raman,

Lal

et al. 2024

Green Chemical Synthesis With Microwaves and Ultrasound

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Triazolothiadizepinylquinolines as potential MetAP-2 and NMT inhibitors: Microwave-assisted synthesis, pharmacological evaluation and molecular docking studies

Cited by 9 publications

References 25 publications

Report on Recently (2017–20) Designed Quinoline‐Based Human Cancer Cell Growth Inhibitors

Report on Recently (2017–20) Designed Quinoline‐Based Human Cancer Cell Growth Inhibitors

Design and synthesis of heterocyclic azole based bioactive compounds: Molecular structures, quantum simulation, and mechanistic studies through docking as multi-target inhibitors of SARS-CoV-2 and cytotoxicity

Microwave‐ and Ultrasonic‐Assisted Coupling Reactions

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