An efficient protocol for the synthesis of novel hetero-aryl chalcone: A versatile synthon for several heterocyclic scaffolds and sensors

Tandel, Shivani N.; Patel, Nilam C.; Kanvah, Sriram; Patel, Paresh N.

doi:10.1016/j.molstruc.2022.133808

Cited by 11 publications

(5 citation statements)

References 30 publications

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“…The π → π* transition (bathochromic shift) and the n → π* transition (hypsochromic shift) are the two main absorption maxima in chalcone derivatives [31][32][33]. The absorption maxima at 370 and 371 nm, respectively, in the UV-Visible spectra of chalcones Ch1 and Ch2, and the UV-Visible spectrum of the chalcone Ch3 to Ch5 and the absorption maxima at 372, 373, and 373 nm, are attributable to the π → π* transition, respectively.…”

Section: Uv-visible Spectroscopymentioning

confidence: 99%

Newer chalcone scaffolds with reactive functional groups: Process, spectral and single crystal XRD studies

Borane,

Deshmukh,

Oza

et al. 2023

Eur J Chem

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Chalcones are versatile scaffolds for the synthesis of various heterocyclic systems with commercial utility. This work describes the synthesis of five novel chalcone derivatives. Syntheses were performed by a simple one-pot, straightforward Claisen-Schmidt condensation catalyzed with pyrrolidine and KOH. The chalcones were prepared by condensation of 4-formylbenzonitrile with different aromatic ketones at room temperature. The structures of all compounds have been investigated by FT-IR, NMR, and HR-MS spectroscopy. In addition, one chalcone structure was characterized by single-crystal XRD study. Crystal data for C21H15NO2 (Ch2): monoclinic, space group P21/c (no. 14), a = 6.5694(3) Å, b = 33.2697(15) Å, c = 7.4516(4) Å, β = 97.563(2)°, V = 1614.47(14) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.083 mm-1, Dcalc = 1.289 g/cm3, 16000 reflections measured (4.898° ≤ 2Θ ≤ 49.99°), 2822 unique (Rint = 0.0249, Rsigma = 0.0196) which were used in all calculations. The final R1 was 0.0484 (I > 2σ(I)) and wR2 was 0.1257 (all data). The absorption maxima of all novel products were evaluated by UV-visible spectroscopy. These well-established structures of all newly prepared chalcone scaffolds with reactive functional groups (i.e. nitrile and 2-propenone) can be exploited as a crucial intermediate in the synthesis of new heterocyclic scaffolds with fluorescence and other applications.

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Section: Uv-visible Spectroscopymentioning

confidence: 99%

Newer chalcone scaffolds with reactive functional groups: Process, spectral and single crystal XRD studies

Borane,

Deshmukh,

Oza

et al. 2023

Eur J Chem

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“…One of the most researched scaffolds is chalcone, which is present in many naturally occurring compounds and has been extensively used in the advancement of science and technology. It has been employed as a dynamic intermediate in the synthesis of several heterocyclic compounds with added value [9,10] . It also plays a crucial part in many biological activities as a result of its special structure with Michael acceptor features, which makes them tolerant to various biomolecules and causes them to react or interact with them [11‐13] .…”

Section: Introductionmentioning

confidence: 99%

“…It has been employed as a dynamic intermediate in the synthesis of several heterocyclic compounds with added value. [9,10] It also plays a crucial part in many biological activities as a result of its special structure with Michael acceptor features, which makes them tolerant to various biomolecules and causes them to react or interact with them. [11][12][13] On the other hand, chalcones are the building blocks for flavonoids and isoflavonoids and exhibit diverse biological properties.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and In Silico Molecular Docking Evaluation of New Series of 1,2,3‐Triazole Derivatives as Potent Antimicrobial Agents

Vellaiyan,

Nagarajaiah,

Shaik

et al. 2024

ChemistrySelect

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Chalcone and triazole scaffolds have demonstrated a crucial role in the advancement of science and technology. Due to their significance, research has proceeded on the design and development of novel benzooxepine connected to 1,2,3‐triazolyl chalcone structures. The new chalcone derivatives produced by benzooxepine triazole methyl ketone and different aromatic carbonyl compounds. Product structures were established by various spectral techniques such as IR, 1H NMR, 13C NMR, and mass specrometric analysis. Among the tested compounds, two compounds exhibited exceptional antibacterial susceptibilities with MIC (Minimum inhibitory concentration) range of 3.59–10.30 μM against the tested S. aureus strain. Few of the compounds displayed superior antifungal activity against F. oxysporum with MIC value range from 3.25‐4.89 μM, when compared to fluconazole (MIC=3.83 μM). In addition, few derivatives demonstrated equivalent antitubercular action against H37Rv strain with MIC range of 2.16–4.90 μM. The capacity of one of the ligand to form a stable compound on the active site of CYP51 from M. tuberculosis (1EA1) was confirmed by docking studies. Additionally, the chalcone‐1,2,3‐triazole hybrids ADME (absorption, distribution, metabolism, and excretion), molecular characteristics, estimation of toxicity, and bioactivity scores were assessed.

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“… Zhang et al (2023) reported the utilization of α , β- unsaturated carbonyl compounds in electrophilic spirocyclization to form 4-halomethyl-2-azaspiro [4.5]decanes. Tandel et al (2022) synthesized highly fluorescent benzothiophene-based chalcone scaffolds by reacting substituted aromatic ketones and benzo [ b ]thiophene carbaldehyde in the presence of catalysts.…”

Section: Introductionmentioning

confidence: 99%

Green synthesis, structure–activity relationships, in silico molecular docking, and antifungal activities of novel prenylated chalcones

Godara,

Kaushik,

Tripathi

et al. 2024

Front. Chem.

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A series of 16 novel prenylated chalcones (5A-5P) was synthesized by microwave-assisted green synthesis using 5-prenyloxy-2-hydroxyacetophenone and different benzaldehydes. Comparisons were also performed between the microwave and conventional methods in terms of the reaction times and yields of all compounds, where the reaction times in the microwave and conventional methods were 1–4 min and 12–48 h, respectively. The synthesized compounds were characterized using different spectroscopic techniques, including IR, 1H-NMR, 13C-NMR, and LC-HRMS. The antifungal activities of all compounds were evaluated against Sclerotium rolfsii and Fusarium oxysporum under in vitro conditions and were additionally supported by structure–activity relationship (SAR) and molecular docking studies. Out of the 16 compounds screened, 2’-hydroxy-4-benzyloxy-5’-O-prenylchalcone (5P) showed the highest activity against both S. rolfsii and F. oxysporum, with ED50 of 25.02 and 31.87 mg/L, respectively. The molecular docking studies of the prenylated chalcones within the active sites of the EF1α and RPB2 gene sequences and FoCut5a sequence as the respective receptors for S. rolfsii and F. oxysporum revealed the importance of the compounds, where the binding energies of the docked molecules ranged from −38.3538 to −26.6837 kcal/mol for S. rolfsii and −43.400 to −23.839 kcal/mol for F. oxysporum. Additional docking parameters showed that these compounds formed stable complexes with the protein molecules.

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An efficient protocol for the synthesis of novel hetero-aryl chalcone: A versatile synthon for several heterocyclic scaffolds and sensors

Cited by 11 publications

References 30 publications

Newer chalcone scaffolds with reactive functional groups: Process, spectral and single crystal XRD studies

Newer chalcone scaffolds with reactive functional groups: Process, spectral and single crystal XRD studies

Design, Synthesis and In Silico Molecular Docking Evaluation of New Series of 1,2,3‐Triazole Derivatives as Potent Antimicrobial Agents

Green synthesis, structure–activity relationships, in silico molecular docking, and antifungal activities of novel prenylated chalcones

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