The first target specific, highly diastereoselective synthesis, design and characterization of pyranoquinolinyl acrylic acid diastereomers as potential α-glucosidase inhibitors

Lavanya, G.; Venkatapathy, K.; Magesh, C.J.; Ramanathan, Mala; Jayasudha, R.

doi:10.1016/j.bioorg.2018.11.026

Cited by 15 publications

(5 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We have reported a highly diastereoselective synthesis of pyranoquinolines and furanoquinolines mediated by chiral Salen-AlCl complex [19] as potential antibacterial agents. More recently, our research group developed a highly diastereoselective synthesis of novel pyranoquinolinyl acrylic acid diasteromers mediated by europium tris [3-(trifluoromethyl)hydroxylmethylene]-(+)-camporate] [20] and mono(bis(2-(4-butylphenyl)imino)methyl)phenoxy)zinc (II) dichloride complex [21] as potential α-glucosidase inhibitors. More recently, we have also reported nanocrystalline CdS thin film as an efficient, recyclable catalyst for the effective synthesis of new class of Biginelli compounds with high oral bioavailability.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, molecular docking, and spectral studies of new class of carbazolyl polyhydroquinoline derivatives as promising antibacterial agents with noncytotoxicity towards human mononuclear cells from peripheral blood

Venkatapathy

Magesh

Lavanya

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

In the present study, we report the design and eco‐benign synthesis of new class of carbazolyl‐1,4‐dihydropyridine (1,4‐CDHP) and carbazolyl‐1,8‐dioxodecahydroacridine (CAD) derivatives via a three‐component coupling reaction of substituted carbazole aldehydes, ethyl acetoacetate/dimedone, and ammonium acetate under solvent‐free conditions at 112°C to 115°C. We also report an efficient one‐pot synthesis of new class of carbazolyl polyhydroquinoline (CPQ) derivatives via a four‐component coupling reaction of substituted ethyl acetoacetate, dimedone, ammonium acetate, and carbazole aldehydes in acetonitrile/water medium (3:1) at 73°C to 75°C in moderate yields. All the products were thoroughly characterized by 1H NMR, 13C NMR, Fourier transform infrared (FTIR), mass spectral, and CHN analysis. The synthesized heterocyclic compounds were evaluated for their in vitro antibacterial activity against pathogenic strains of both Gram‐negative and Gram‐positive bacteria. Minimum inhibitory concentration (MIC) of the active compounds was evaluated by macrodilution method. The CPQ derivative (8a) displayed superior antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, and Salmonella typhi with the MIC values of 16.0 to 32.0 μg/mL in comparison with the reference drug. The mechanism of antibacterial action of the CPQ derivatives was investigated via scanning electron microscope (SEM) studies. The molecular docking studies indicate that the CPQ derivative (8a) binds to the cell wall protein of E coli and P aeruginosa by formation of hydrogen bonds with amino acid residues (TYR328 and GLU249) of the bacterial cell wall protein. The 1,4‐CDHP, CAD, and CPQ derivatives were either noncytotoxic or exhibited minimal cytotoxicity towards human mononuclear cells from peripheral blood. All the products were evaluated for Lipinski rule of five (RO5) and were found to have good oral bioavailability.

show abstract

Section: Introductionmentioning

confidence: 99%

Design, synthesis, molecular docking, and spectral studies of new class of carbazolyl polyhydroquinoline derivatives as promising antibacterial agents with noncytotoxicity towards human mononuclear cells from peripheral blood

Venkatapathy

Magesh

Lavanya

et al. 2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…[18] The aza-Diels-Alder [4 + 2] cycloaddition displays a very productive and efficient role as a source of bioactive compounds in many drug discovery programs. [19] For example, target cyclic ether-annulated tetrahydroquinolines possess antitumor, [20] antiproliferative, [21] analgetic, [22] bactericidal [23] (including antimycobacterial [3e,24] ), and α-glucosidase inhibitory [25] activities (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition

et al. 2022

View full text Add to dashboard Cite

Electrochemical synthesis of cyclic ether‐annulated tetrahydroquinolines from imines and cyclic ethers in an undivided cell under constant current conditions was developed. The electrosynthesis proceeds via the enol ether formation from ethers following the aza‐Diels‐Alder [4+2] cycloaddition. The method is applicable to a wide range of imines and results in the desired products in yields of 23 to 75%. In situ preparation of imines from the corresponding anilines and aldehydes led to mostly the same yields of tetrahydroquinolines. No cycloaddition products were formed using the chemical oxidants. Synthesized cyclic ether‐annulated tetrahydroquinolines exhibit high antifungal activity, which is superior to the commercial fungicide Triadimefon.

show abstract

“…More recently we have reported the highly diastereoselective synthesis of a novel pyranoquinolinyl acrylic acid diasteromers catalysed by chiral Europium tris[3‐(trifluoro methyl)hydroxylmethylene]‐(+)‐camporate] and Mono (bis(2‐(4‐butylphenyl)imino) methyl)phenoxy)zinc (II)dichloride complex as potential α‐Glucosidase inhibitors. More recently our team has also reported phenol formaldehyde liquid resin as an efficient, recyclable catalyst and medium for the effective synthesis of biginelli compounds .…”

Section: Introductionmentioning

confidence: 99%

The First Recyclable, Nanocrystalline CdS Thin Film Mediated Eco‐benign Synthesis Of Hantzsch 1, 4 Dihyropyridines, 1, 8‐Dioxodecahydroacridine and Polyhydroquinolines derivatives

Lavanya¹,

Venkatapathy²,

Magesh³

et al. 2019

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

In the present study, we report a recyclable, nanocrystalline CdS thin film mediated efficient one‐pot, three component synthesis of Hantzsch 1, 4 Dihydropyridine in good yields. The catalyst is also effective for the efficient synthesis of Polyhydroquinoline and 1, 8‐dioxodecahydroacridine derivatives in good to excellent yields. The CdS thin film catalyst was prepared by chemical bath deposition (CBD) technique. The cadmium sulphide thin film was characterized by powder XRD and FT‐IR studies. The average crystallite size (D) was calculated from powder XRD by using Scherrer formula and SEM analysis. The elemental composition of the CdS thin film was established by EDS analysis. The effect of temperature, substituent's, catalyst loading and mole ratio on the reaction was also studied. All the products were thoroughly characterized by 1H‐NMR, 13C‐NMR, FT‐IR, Mass spectral and CHN analysis. A plausible mechanism for the CdS thin film catalyzed synthesis of 1, 4 DHP's is proposed. The heterogeneous catalyst could be easily recovered from the reaction mixture and successively reused at least five times without loss of activity.

show abstract

The first target specific, highly diastereoselective synthesis, design and characterization of pyranoquinolinyl acrylic acid diastereomers as potential α-glucosidase inhibitors

Cited by 15 publications

References 19 publications

Design, synthesis, molecular docking, and spectral studies of new class of carbazolyl polyhydroquinoline derivatives as promising antibacterial agents with noncytotoxicity towards human mononuclear cells from peripheral blood

Design, synthesis, molecular docking, and spectral studies of new class of carbazolyl polyhydroquinoline derivatives as promising antibacterial agents with noncytotoxicity towards human mononuclear cells from peripheral blood

Electrochemical Synthesis of Tetrahydroquinolines from Imines and Cyclic Ethers via Oxidation/Aza‐Diels‐Alder Cycloaddition

The First Recyclable, Nanocrystalline CdS Thin Film Mediated Eco‐benign Synthesis Of Hantzsch 1, 4 Dihyropyridines, 1, 8‐Dioxodecahydroacridine and Polyhydroquinolines derivatives

Contact Info

Product

Resources

About