Design, synthesis, spectral characterization and molecular docking studies of novel pyranoquinolinyl dihydropyridine carboxylates as potential antibacterial agents including Vibrio cholerae with minimal cytotoxity towards fibroblast cell line (L-929)

Lavanya, G.; Magesh, C.J.; Venkatapathy, K.; Perumal, Paramasivan T.; Prema, S.

doi:10.1016/j.bioorg.2020.104582

Cited by 12 publications

(8 citation statements)

References 23 publications

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“…Since then, the antitubercular properties of other DHP derivatives have been reported by many other researchers ( Trivedi et al, 2011 ; Desai et al, 2015 ; Zandhaghighi et al, 2017 ; Venugopala et al, 2021 ). DHPs have been also evaluated as antimicrobials against other pathogenic bacteria including S. aureus ( Ceviz et al, 1997 ; Olejnikova et al, 2014 ; Mahmoodi et al, 2015 ; Nkosi et al, 2016 ; Nosrati et al, 2021 ), E. coli ( Murthy et al, 2012 ; Olejnikova et al, 2014 ; Mahmoodi et al, 2015 ; Nkosi et al, 2016 ; Ahamed et al, 2018 ), Pseudomonas aeruginosa ( Mahmoodi et al, 2015 ; Nkosi et al, 2016 ; Ahamed et al, 2018 ), Vibrio cholerae ( Lavanya et al, 2021 ) and Klebsiella pneumoniae ( Murthy et al, 2012 ); but also against parasites ( Núñez-Vergara et al, 1997 ; Palit and Ali, 2008 ; Reimao et al, 2010 ; Pollo et al, 2017 ; Jeddi et al, 2021 ) and fungi ( Chhillar et al, 2006 ; Jezikova et al, 2017 ; Ahamed et al, 2018 ). This class of molecules have been also studied as inhibitors of bacterial transmembrane efflux pumps, acting thereby as enhancers of the action of conventional antibiotics ( Lentz et al, 2016 , 2018 , 2019 ).…”

Section: Discussionmentioning

confidence: 99%

1,4-Dihydropyridine as a Promising Scaffold for Novel Antimicrobials Against Helicobacter pylori

et al. 2022

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The increasing occurrence of multidrug-resistant strains of the gastric carcinogenic bacterium Helicobacter pylori threatens the efficacy of current eradication therapies. In a previous work, we found that several 1,4-dihydropyridine (DHP)-based antihypertensive drugs exhibited strong bactericidal activities against H. pylori by targeting the essential response regulator HsrA. To further evaluate the potential of 1,4-DHP as a scaffold for novel antimicrobials against H. pylori, we determined the antibacterial effects of 12 novel DHP derivatives that have previously failed to effectively block L- and T-type calcium channels. Six of these molecules exhibited potent antimicrobial activities (MIC ≤ 8 mg/L) against three different antibiotic-resistant strains of H. pylori, while at least one compound resulted as effective as metronidazole. Such antimicrobial actions appeared to be specific against Epsilonproteobacteria, since no deleterious effects were appreciated on Escherichia coli and Staphylococcus epidermidis. The new bactericidal DHP derivatives targeted the H. pylori regulator HsrA and inhibited its DNA binding activity according to both in vitro and in vivo analyses. Molecular docking predicted a potential druggable binding pocket in HsrA, which could open the door to structure-based design of novel anti-H. pylori drugs.

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Section: Discussionmentioning

confidence: 99%

1,4-Dihydropyridine as a Promising Scaffold for Novel Antimicrobials Against Helicobacter pylori

et al. 2022

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“…The designed approach involved the Michael addition and inverse electrodemand Alder reaction (IED) to generate pyranoquinolinyl dihydropyridine carboxylates (106) in good yields (Scheme 25). [37] In 2021, I presented a multicomponent methodology for the synthesis of fused polycyclic functionalized pyridines (110, 111), using In(OTf) 3 as the catalyst. With a wide range of substrates containing dihydrobenzoquinoline, azafluorene, azafluorenone, pyrido-coumarin, and benzocycloheptapyridine frameworks, the suggested method provided very high yield products.…”

Section: Multicomponent Reactionsmentioning

confidence: 99%

Indium Triflate's Transformative Role in Modern Organic Synthesis: A Five‐Year Survey of Functionalization, Cyclization, and Multicomponent Reactions

Jamshaid

2024

ChemistrySelect

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Indium triflate (In(OTf)3) has proven to be a powerful and sustainable catalyst in the synthesis of modern organic compounds, enabling a variety of transformations such as functionalization, cyclization, and multicomponent reactions. To provide insight into the most recent methods and applications, this study attempts to provide a comprehensive and up‐to‐date summary of these advances in the application of indium triflate as a catalyst in organic synthesis, focusing on the last five years of literature. The application of indium triflate as opposed to alternative indium(III) catalysts in organic transformations will be the main emphasis of this review, which will cover recent developments through research articles and reviews published between 2019 and 2023. This minireview will make a significant contribution to the existing literature by consolidating recent advancements in the use of indium triflate in modern organic synthesis.

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“…Expectedly, due to the lower nucleophilicity of alcohols and phenols as compared to (at least aliphatic) amines, examples of successful sulfonate syntheses starting from sulfonyl chlorides bearing a hydroxy group are relatively uncommon. Nevertheless, at certain conditions, phenol, [371] alcohol, [264] and even aniline [374,375] moieties were tolerated.…”

Section: Selective Reactions Proceeding At the So 2 CL Moietymentioning

confidence: 99%

Chemoselective Reactions of Functionalized Sulfonyl Halides

Liashuk,

Andriashvili,

Tolmachev

et al. 2023

The Chemical Record

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Chemoselective transformations of functionalized sulfonyl fluorides and chlorides are surveyed comprehensively. It is shown that sulfonyl fluorides provide an excellent selectivity control in their reactions. Thus, numerous conditions are tolerated by the SO2F group – from amide and ester formation to directed ortho‐lithiation and transition‐metal‐catalyzed cross‐couplings. Meanwhile, sulfur (VI) fluoride exchange (SuFEx) is also compatible with numerous functional groups, thus confirming its title of “another click reaction”. On the contrary, with a few exceptions, most transformations of functionalized sulfonyl chlorides typically occur at the SO2Cl moiety.

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Design, synthesis, spectral characterization and molecular docking studies of novel pyranoquinolinyl dihydropyridine carboxylates as potential antibacterial agents including Vibrio cholerae with minimal cytotoxity towards fibroblast cell line (L-929)

Cited by 12 publications

References 23 publications

1,4-Dihydropyridine as a Promising Scaffold for Novel Antimicrobials Against Helicobacter pylori

1,4-Dihydropyridine as a Promising Scaffold for Novel Antimicrobials Against Helicobacter pylori

Indium Triflate's Transformative Role in Modern Organic Synthesis: A Five‐Year Survey of Functionalization, Cyclization, and Multicomponent Reactions

Chemoselective Reactions of Functionalized Sulfonyl Halides

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