Synthesis, molecular docking and extensive structure activity relationship of substituted DHP derivatives: a new class of herbicides

Agrwal, Akansha; Verma, Anil Kumar; Chantola, Neelam; Verma, Shivani; Kasana, Virendra

doi:10.1080/03601234.2022.2062188

Cited by 5 publications

(9 citation statements)

References 76 publications

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“…The signal appeared at 172.5 ppm concerning the carbon atom of the carbonyl group. The carbon atom of the carbonyl group showed chemical shifts in the reported value of 167.3-170.0 ppm [22].…”

Section: C-nmr Resultsmentioning

confidence: 95%

“…The chemical shift at 55.8 ppm is assigned to the carbon atom of the O-CH 3 group. This assignment is based on the previously reported chemical shifts of the carbon atom of this group [21][22]. The chemical shift at 59.9 ppm is due to the carbon atom of the CH 2 group.…”

Section: C-nmr Resultsmentioning

confidence: 99%

“…This peak is attributed to the methoxy protons (O-CH 3 group). The chemical shifts of the protons of the O-CH 3 group are reported in the range of 3.65-3.8 ppm [21][22][23]. The chemical shift of the benzene ring protons is found at 7.487 ppm.…”

Section: H-nmr Resultsmentioning

confidence: 99%

“…The spectrum of the ligand, S2, exhibits a chemical shift at 18.53 ppm, which is assigned to the carbon atom of the methyl group, which is attached to the azomethine group (-N=C-CH 3 ). It was reported that the chemical shifts of the carbon atom in the methyl group of C-CH 3 in the range 19.09-19.87 [22]. The chemical shift at 21.3 ppm is attributed to the carbon atom of the methyl group, which is attached to the carbonyl group (-(CO)-CH 3 ).…”

Section: C-nmr Resultsmentioning

confidence: 99%

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Synthesis, DFT Calculations, DNA Interaction, and Antimicrobial Studies of Some Mixed Ligand Complexes of Oxalic Acid and Schiff Base Trimethoprim with Various Metal Ions

Abdalrazaq

Jbarah²,

Al‐Noor³

et al. 2022

Indones. J. Chem.

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Mixed ligand metal complexes are synthesized from oxalic acid with Schiff base, and the Schiff base was obtained from trimethoprim and acetylacetone. The synthesized complexes were of the type [M(L1)(L2)], where the metal, M, is Ni(II), Cu(II), Cr(III), and Zn(II), L1 corresponds to the trimethoprim ((Z)-4-((4-amino-5-(3,4,5-trimethoxybenzyl)pyrimidine-2-yl)imino)pentane-2-one) as the first ligand and L2 represent the oxalate anion ( ) as a second ligand. Characterization of the prepared compounds was performed by elemental analysis, molar conductivity, magnetic measurements, 1H-NMR, 13C-NMR, FT-IR, and Ultraviolet-visible (UV-Vis) spectral studies. The recorded infrared data is reinforced with density functional theory (DFT) calculations. Also, the recorded and calculated IR spectra of the complexes suggested that the coordination of Schiff base is a bidentate ligand with Cu and Ni complexes and a tridentate ligand with Co, Cr, and Zn complexes. The electronic structures of the complexes were investigated by DFT calculations, showing several degrees of HOMO-LUMO energy gaps between complexes. The complexes were studied for their DNA interaction activities. The synthesized ligand and its metal complexes were evaluated for antimicrobial properties against bacterial strains of Bacillus subtilis (G+), Enterobacter cloacae (G-), and Staphylococcus aureus (G+). These complexes considered in this study showed good antimicrobial activity.

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Section: C-nmr Resultsmentioning

confidence: 95%

Section: C-nmr Resultsmentioning

confidence: 99%

Section: H-nmr Resultsmentioning

confidence: 99%

Section: C-nmr Resultsmentioning

confidence: 99%

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Synthesis, DFT Calculations, DNA Interaction, and Antimicrobial Studies of Some Mixed Ligand Complexes of Oxalic Acid and Schiff Base Trimethoprim with Various Metal Ions

Abdalrazaq

Jbarah²,

Al‐Noor³

et al. 2022

Indones. J. Chem.

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“…[15] Additionally, DHP can be readily synthetized using a number of methods, [16 -23] which provides access to a broad chemical structural diversity, leading to several pharmacological and biological activities, including anticancer, [24] antitubercular, [25] antimicrobial, [26] antifungal, [27] antiproliferative, [28] anti-oxidant [29] and pre-emergence herbicide. [30] In order to understand the chemical interactions between electron chain inhibitors in the binding site of PSII as well as to elucidate fundamental biochemical processes, molecular docking represents an important tool in the development and discovery of new herbicides. [31 -36] Recently, the PsbA protein isolated from Thermosynechococcus elongates (PDB code: 4V82) has been used to predict the chemical interactions between quinone B binding site and small molecules, such as the triazine derivative with herbicidal activity against Phalaris minor weed, [37] the diketopiperazine, an algicidal compound produced by Pseudoruegeria sp.…”

Section: Introductionmentioning

confidence: 99%

Binding Properties of Photosynthetic Herbicides: Photosynthetic Activity and Molecular Docking Approach towards 1,4‐Dihydropyridines Derivatives

Soares

Basso

Santos

et al. 2022

Chemistry & Biodiversity

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In the current work, we describe the synthesis of 1,4‐dihydropyridine (1,4‐DHP) derivatives via Hantzsch multicomponent reaction and their evaluation as photosystem II (PSII) inhibitors through chlorophyll a fluorescence bioassay. Among all the compounds tested, 1,1′‐(2,4,6‐trimethyl‐1,4‐dihydropyridine‐3,5‐diyl)bis(ethan‐1‐one) (4b) showed best results, reducing the parameters performance index on absorption basis (PIabs) and electron transport per reaction center by 61 % and 49 %, respectively, as compared to the control. These results indicate the inhibitory activity of PSII over the electron transport chain. Additionally, a molecular docking approach using the protein D1 (PDB code 4V82) was performed in order to assess the structure‐activity relationship among the 1,4‐DHP derivatives over the PSII, which revealed that both, size of the group at position 4 and the carbonyl groups at the dihydropyridine ring are important for the ligand's interaction, particularly for the hydrogen‐bonding interaction with the residues His215, Ser264, and Phe265. Thus, the optimization of these molecular features is the aim of our research group to extend the knowledge of PSII electron chain inhibitors and the establishment of new potent bioactive molecular scaffolds.

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β‐amino carbonyl derivatives: Synthesis, Molecular Docking, ADMET, Molecular Dynamic and Herbicidal studies.

et al. 2022

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In the current report, 3D structures of the enzyme Lathyrus aphaca Ribulose bisphosphate carboxylase (LArbcL) was modeled using homology modeling. The structures of the synthesized β‐amino carbonyl derivatives were made by means of “Chem Draw ultra‐12.0”, ADMET prediction were conducted to compute physicochemical properties. Pharmacokinetics studies and the molecular docking study of the synthesized compounds were performed against Lathyrus aphaca Ribulose bisphosphate carboxylase. Docking experiments verified a significant Docking Score values between 6.2 to 7.3 kcal mol−1. The highest‐ranking complexes obtained from docking results were subjected to 100 ns Molecular Dynamics simulations using Gromacs program to investigate the constancy of the docked “protein–ligand complexes” as well as the oscillation and conformational variations that occur during protein–ligand interaction. The synthesized derivatives were screened for pre‐emergence and post‐emergence herbicidal activity adjacent to weed species named Lathyrus aphaca with concentrations of “0.005 M, 0.01 M and 0.02 M”, and the activity was compared with Butachlor and penoxulum which are standard herbicide. Every single synthesized compounds show good to moderate activity.

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Synthesis, molecular docking and extensive structure activity relationship of substituted DHP derivatives: a new class of herbicides

Cited by 5 publications

References 76 publications

Synthesis, DFT Calculations, DNA Interaction, and Antimicrobial Studies of Some Mixed Ligand Complexes of Oxalic Acid and Schiff Base Trimethoprim with Various Metal Ions

Synthesis, DFT Calculations, DNA Interaction, and Antimicrobial Studies of Some Mixed Ligand Complexes of Oxalic Acid and Schiff Base Trimethoprim with Various Metal Ions

Binding Properties of Photosynthetic Herbicides: Photosynthetic Activity and Molecular Docking Approach towards 1,4‐Dihydropyridines Derivatives

β‐amino carbonyl derivatives: Synthesis, Molecular Docking, ADMET, Molecular Dynamic and Herbicidal studies.

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