Ultrasound-assisted multicomponent synthesis of pyrido[2,3-d]pyrimidine derivatives and their DFT calculations: A green approach

Thakral, Ankita; Bharti, Ruchi; Thakur, Ajay; Verma, Monika; Sharma, Renu

doi:10.1016/j.matpr.2022.11.380

Cited by 3 publications

(3 citation statements)

References 28 publications

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“…In contrast, regions characterized by the highest electronegative potential emerge as a vibrant red zone, symbolizing an electron-rich environment. This approach, underpinned by sound scientific principles and supported by prior research, 15,21,26 provides an intricate map of the compounds' electrostatic landscapes. It offers a nuanced perspective on how these compounds interact with their surroundings, shedding light on their electron distribution, polarity, and electrostatic characteristics.…”

Section: Molecular Electrostatic Potential Studymentioning

confidence: 99%

Thiosemicarbazone ligands based transition metal complexes: A multifaceted investigation of antituberculosis, anti‐inflammatory, antibacterial, antifungal activities, and molecular docking, density functional theory, molecular electrostatic potential, absorption, distribution, metabolism, excretion, and toxicity studies

Kumar,

Devi,

Dubey

et al. 2024

Applied Organom Chemis

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Infectious diseases have held a prominent place in the history of humanity, shaping societies, influencing medical advances, and affecting the lives of individuals on a global scale and are caused by a variety of pathogens that lead to a wide range of illnesses. Among this diverse group of ailments, tuberculosis (TB), inflammatory conditions, and various bacterial and fungal diseases stand out as major challenges that have long plagued humanity. Thus, the aim of this research is delve a significant combatting agent against TB, inflammation, bacterial and fungal deformities. To explore the above facts and to examine the therapeutic potential, the previously synthesized thiosemicarbazones (1–2) and their Co (II), Ni (II), Cu (II), Zn (II) complexes (3–10) of benzaldehydes and 4‐(4‐ethylphenyl)‐3‐thiosemicarbazide were proposed for in vitro investigation by microplate Alamar Blue, bovine serum albumin, and serial dilution methods. The compound (10) demonstrates almost double effectiveness in controlling TB dysfunction (minimum inhibitory concentration [MIC] value 0.006 ± 0.001 μmol/mL), surpassing streptomycin, whereas (6) and (9) have comparable TB inhibition efficacy to streptomycin. The compound (10) also has the highest potency for inflammation (6.75 ± 0.09 μM), bacterial (0.0066 μmol/mL), and fungal (0.0066 μmol/mL) ailments among the tested compounds with comparable inhibition abilities to their respective standard drugs. Moreover, molecular docking (targeting the PDB ID 6H53 and 1CX2 proteins), density functional theory (DFT), molecular electrostatic potential (MESP), and absorption, distribution, metabolism, excretion, and toxicity (ADMET) evaluations were performed against the highly efficient ligand (2) and its complexes (7–10) to validate the in vitro results. In this endeavor, our aim is to actively participate in the continuous initiatives aimed at fighting infectious diseases and enhancing global health and overall well‐being.

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Section: Molecular Electrostatic Potential Studymentioning

confidence: 99%

Thiosemicarbazone ligands based transition metal complexes: A multifaceted investigation of antituberculosis, anti‐inflammatory, antibacterial, antifungal activities, and molecular docking, density functional theory, molecular electrostatic potential, absorption, distribution, metabolism, excretion, and toxicity studies

Kumar,

Devi,

Dubey

et al. 2024

Applied Organom Chemis

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“…In 2023, Thakral and colleagues [115] carried out a research study where they successfully developed an eco-friendly multicomponent reaction involving 1,3-diketones, cinnamaldehyde 128, and aminopyrimidine 47 derivatives. This reaction took place in a clean setting, utilizing ultrasonic irradiation as an efficient method for the synthesis of pyridopyrimidine 129-130 derivatives.…”

Section: Ultrasound-assisted Synthesis Of Pyrido[23-d]pyrimidine Comp...mentioning

confidence: 99%

Furo, Pyrano, and Pyrido[2,3‐d]Pyrimidines: A Comprehensive Review of Synthesis and Medicinal Applications

Rezaeifard,

Bakherad,

Navidpour

et al. 2024

ChemistrySelect

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Due to their extensive applications in pharmaceuticals and natural substances, organic synthesis and heterocyclic compounds have been at the forefront of research for many years. Pyrimidine is one of the heterocyclic compounds that have various derivatives with promising biological and pharmacological properties. This review article covers the synthesis and biological effects of pyrimidine derivatives, such as pyrano[2,3‐d]pyrimidines, pyrido[2,3‐d]pyrimidines, and furo[2,3‐d]pyrimidines. The compounds discussed in this review have a wide range of biological activities. Recent advances in green chemistry have led to the development of eco‐friendly synthetic methods for producing these bioactive heterocycles. This review aims to present various synthetic methods and biological effects of these compounds and provide new opportunities for organic chemists to develop potent nitrogen‐ and oxygen‐containing heterocycles for future applications. The review highlights examples of successful syntheses and applications of pyrimidine derivatives in the fields of antibacterial, antifungal, anticancer, enzyme inhibition, and antiviral research.

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“…The reactivity of molecules and many other significant structural characteristics can be identified through electronic structure calculations. [46][47][48][49] In this study, we have used Gaussian 09W and Gauss view 6.0.16 software to perform the DFT. The B3LYP method and 6-311G(d,p) basis set were used for the DFT calculations.…”

Section: Antifungal Activitymentioning

confidence: 99%

Ultra-Sonicated One-Pot Synthesis of Potent Bioactive Biscoumarin and Polycyclic Pyranodichromenone Scaffolds in Aqueous Media: A Complementary Tool to Organic Synthesis

et al. 2023

Self Cite

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Present study involves the synthesis of bis-coumarins and novel polycyclic pyranodichromenones using a catalyst-free approach under ultrasonic irradiation in an aqueous medium. The chemical structures of the synthesized compounds were characterized using FTIR, 1H NMR, and 13C NMR spectroscopy. The antibacterial and antifungal activities of the compounds were evaluated against Gram-positive (S. aureus, B. cereus) and Gram-negative bacteria (P. aeruginosa, E. coli), as well as the fungus C. albicans, using the disc diffusion method. Several compounds exhibited excellent activity against the tested microorganisms. Moreover, the antioxidant potential of the synthesized products was assessed using 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radical scavenging, and total antioxidant capacity (TAC) assays. Promising antioxidant activity was observed for certain compounds. Computational studies using density functional theory (DFT) were conducted to investigate the molecular reactivity and electronic properties of the synthesized compounds. Quantum mechanical parameters such as Ionization Potential (IP), Electron Affinity (EA), Mulliken Electronegativity (χ), Chemical Potential (μ), and Electrophilicity Index (ω) were calculated. The study highlights the efficiency and eco-friendliness of ultrasonic-assisted processes, contributing to the advancement of sustainable chemistry.

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Ultrasound-assisted multicomponent synthesis of pyrido[2,3-d]pyrimidine derivatives and their DFT calculations: A green approach

Cited by 3 publications

References 28 publications

Furo, Pyrano, and Pyrido[2,3‐d]Pyrimidines: A Comprehensive Review of Synthesis and Medicinal Applications

Ultra-Sonicated One-Pot Synthesis of Potent Bioactive Biscoumarin and Polycyclic Pyranodichromenone Scaffolds in Aqueous Media: A Complementary Tool to Organic Synthesis

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