Solvent-free synthesis, spectral, crystal study and DFT calculations of (E)-1-benzyl-N-(4-fluorobenzylidene)piperidin-4-amine and (E)-1-benzyl-N-(naphthalen-2-ylmethylene)piperidin-4-amine

Kumar, Naresh; Mayavel, P.; Muthuvel, I.; Thirunarayanan, Ganesamoorthy

doi:10.1016/j.cdc.2020.100547

Cited by 4 publications

(2 citation statements)

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“…As well, pyridines, purines and pyrimidines are other examples of biologically active cyclic nitrogen heterocycles. [6] While, thieno [2,3-d]-pyrimidines are the key pharmacological bicyclic heterocyclic molecules belonging to the class of fused pyrimidines. Several synthetic methods have been used for the synthesis of thieno [2,3-d]-pyrimidine cognates, and each approachhas a unique starting chemical substrate.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Molecular Docking Studies of Integrated Benzylidenethiazolidine‐2,4‐Dione and Thieno[2,3‐d]pyrimidine‐6‐Carboxylate Derivatives as Potent Antidiabetic agents

Nagaraju,

Rajeswari,

Vedasree

et al. 2023

ChemistrySelect

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The present work describes the synthesis of new series of 5‐arylidene‐thiazolidine‐2,4‐dione, thieno[2,3‐d]pyrimidine‐6‐carboxylate derivatives 9 a–o. A variety of spectroscopic techniques like IR, 13CNMR, 1HNMR and LCMS were used to establish the presence of the every synthesized scaffold. The antioxidant activity of the target compounds has been studied by three different methods indicated the significant DPPH, NO and H2O2. Further, all the derivatives were evaluated for the in vitro antidiabetic potential against human pancreatic α‐amylase (PDB ID: 5NN3) and human lysosomal acid α‐glucosidase (PDB ID: 2QV4) enzymes followed by Molecular docking studies to ascertain the binding interactions of the compounds with the enzymes. The compounds 9 b and 9 g containing methoxy groups were found to exhibit potent antidiabetic and antioxidant activity. Therefore, it was rationalized that two privileged pharmacophores i. e. aryledenethiazolidine‐2,4‐dione and thieno[2,3‐d]pyrimidine‐6‐carboxylate assimilated hybrids, may be beneficial as lead template for the advance of future anti‐diabetic agents. Thus, benzylidenethiazolidine‐2,4‐dione and thieno[2,3‐d], the two preferred pharmacophores, were rationalized. Assimilation of ‐pyrimidine‐6‐carboxylate hybrids could be advantageous as a lead template for the development of new anti‐diabetic drugs.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Molecular Docking Studies of Integrated Benzylidenethiazolidine‐2,4‐Dione and Thieno[2,3‐d]pyrimidine‐6‐Carboxylate Derivatives as Potent Antidiabetic agents

Nagaraju,

Rajeswari,

Vedasree

et al. 2023

ChemistrySelect

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“…The surface properties were analysed using 3D dnorm surfaces [40] . This research discusses the HOMO‐LUMO energy gap, as well as crystal structure aspects such as 3D energy framework calculations and molecular lattice energy estimates, [41] and density functional theory (DFT) calculations [42] . Finally, the chemically active areas of the molecule are determined by studying the molecular electrostatic potential map.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Sagar,

Kumara,

et al. 2023

ChemistrySelect

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The microwave‐assisted synthesis, crystallographic studies, in‐silico docking and the evaluation of in‐vitro biological activities of 2‐(3,4‐dimethoxy)‐6‐(substituted phenyl)‐ imidazo[2,1‐b][1,3,4]thiadiazole‐5‐carbaldehydes is represented here. Single‐crystal X‐ray diffraction experiments were used to identify the crystal structure of the 6‐(4‐chlorophenyl)‐2‐(3,4‐dimethoxybenzyl)imidazo[2,1‐b][1,3,4]thiadiazole‐5‐carbaldehyde. Using fingerprint plots, Hirshfeld surface analysis was used to confirm the contributions of distinct intermolecular interactions in the development of the crystal packing. Further, density functional theory calculations were employed to calculate the molecule's electronic properties. The chemically active regions on the molecule are identified by analysing the molecular electrostatic potential map. in‐silico studies revealed that the molecules can be effectively used as antibacterial agents by taking the 3q82 receptor with chloramphenicol as a standard. As compared to the chloramphenicol standard, in‐vitro tests showed that molecules 4 a, 4 b, 4 c, and 4 f had a zone of inhibition that ranged from 9 to 11 mm against both Gram‐positive (Bacillus subtilis) and Gram‐negative (Escherichia coli) bacteria. The minimum inhibitory concentration was between 40 to 70 μg/ml. These compounds′ Hydroxyl free radical scavenging activity was between 40 to 85 %. Whereas, DPPH radical scavenging activity was between 40 and 70 %. Percentage hemolysis or cell protective activity of the compounds was ineffective at 20–40 %.

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Solid acid-catalyzed green synthesis of bis-Schiff bases: Spectroscopic, DFT, molecular docking, and ADMET studies

Dinesh kumar,

Thirunarayanan,

Elancheran

et al. 2025

Journal of Molecular Structure

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Solvent-free synthesis, spectral, crystal study and DFT calculations of (E)-1-benzyl-N-(4-fluorobenzylidene)piperidin-4-amine and (E)-1-benzyl-N-(naphthalen-2-ylmethylene)piperidin-4-amine

Cited by 4 publications

References 55 publications

Design, Synthesis, and Molecular Docking Studies of Integrated Benzylidenethiazolidine‐2,4‐Dione and Thieno[2,3‐d]pyrimidine‐6‐Carboxylate Derivatives as Potent Antidiabetic agents

Design, Synthesis, and Molecular Docking Studies of Integrated Benzylidenethiazolidine‐2,4‐Dione and Thieno[2,3‐d]pyrimidine‐6‐Carboxylate Derivatives as Potent Antidiabetic agents

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Solid acid-catalyzed green synthesis of bis-Schiff bases: Spectroscopic, DFT, molecular docking, and ADMET studies

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