A facile one-pot green synthesis of novel 2-amino-4H-chromenes: antibacterial and antioxidant evaluation

Maddahi, Mona; Asghari, Sakineh; Pasha, Ghasem Firouzzadeh

doi:10.1007/s11164-022-04893-5

Cited by 8 publications

(3 citation statements)

References 46 publications

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“…4H-Chromene is an important heterocyclic compound, and its unique structure and biological properties have made it a valuable target for medicinal chemists in the development of new drug candidates [3,4]. 4H-Chromene scaffold possesses antiinflammatory [5], antibacterial [6,7], antifungal [8], antitumor [9], antioxidant [7], antileishmanial [10], and anticancer [11,12], making it an attractive platform for drug discovery. The efficient synthesis of ACC, therefore, garnered significant interest in the scientific community [13].…”

Section: Introductionmentioning

confidence: 99%

2‐Aminopyrazine catalyzed three‐component and one‐pot construction of 2‐amino‐4H‐chromene‐3‐carbonitrile by mortar‐pestle grinding and molecular docking studies

Edapu,

Boodida,

Pagadala

et al. 2024

J Chinese Chemical Soc

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A highly efficient and environmentally friendly method for the synthesis of 2‐amino‐4H‐chromene‐3‐carbonitrile (ACC) derivatives has been successfully established. This innovative, solvent‐free approach involves a tandem three‐component and one‐pot reaction utilizing arylaldehyde, dicyanomethane, and dimedone/cyclohexane‐1,3‐dione, catalyzed by 2‐aminopyrazine under the mortar‐pestle grinding technique. Key attributes of this synthetic strategy include its simplicity, high efficiency, cost‐effectiveness, absence of column chromatography, shorter reaction times (18–40 min), and consistently high yields (89%–96%). Furthermore, computational studies have been conducted against the 4RHT protein using the synthesized compounds.

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Section: Introductionmentioning

confidence: 99%

2‐Aminopyrazine catalyzed three‐component and one‐pot construction of 2‐amino‐4H‐chromene‐3‐carbonitrile by mortar‐pestle grinding and molecular docking studies

Edapu,

Boodida,

Pagadala

et al. 2024

J Chinese Chemical Soc

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“…Moreover, Chromene derivatives are an essential class of oxygen-containing heterocyclic compounds that have attracted researcher's attention because of their applications in pigments, cosmetics, and agrochemicals, and their wide range of biological activities 17 , 18 like anti-diabetic 19 , antibacterial 20 , antioxidant 21 , anti-cancer 22 and antiviral activities 23 . Given that chromene sulfonamide hybrids have been shown variable biological activities 24 – 26 , and based on our previous works on the synthesis of sulfonamide hybrids 27 – 31 , accordingly, we were motivated to design and synthesize some novel derivatives of these hybrids (Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

Evaluation of antibacterial, cytotoxicity, and apoptosis activity of novel chromene-sulfonamide hybrids synthesized under solvent-free conditions and 3D-QSAR modeling studies

Ghomashi,

Damavandi

et al. 2024

Sci Rep

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In this study, eleven novel chromene sulfonamide hybrids were synthesized by a convenient method in accordance with green chemistry. At first, chromene derivatives (1–9a) were prepared through the multi-component reaction between aryl aldehydes, malononitrile, and 3-aminophenol. Then, synthesized chromenes were reacted with appropriate sulfonyl chlorides by grinding method to give the corresponding chromene sulfonamide hybrids (1–11b). Synthesized hybrids were obtained in good to high yield and characterized by IR, 1HNMR, 13CNMR, CHN and melting point techniques. In addition, the broth microdilution assay was used to determine the minimal inhibitory concentration of newly synthesized chromene-sulfonamide hybrids. The MTT test was used to determine the cytotoxicity and apoptotic activity of the newly synthesized compounds against fibroblast L929 cells. The 3D‑QSAR analysis confirmed the experimental assays, demonstrating that our predictive model is useful for developing new antibacterial inhibitors. Consequently, molecular docking studies were performed to validate the findings of the 3D-QSAR analysis, confirming the potential binding interactions of the synthesized chromene-sulfonamide hybrids with the target enzymes. Molecular docking studies were employed to support the 3D-QSAR predictions, providing insights into the binding interactions between the newly synthesized chromene-sulfonamide hybrids and their target bacterial enzymes, thereby reinforcing the potential efficacy of these compounds as antibacterial agents. Also, some of the experimental outcomes supported or conflicted with the pharmacokinetic prediction (especially about compound carcinogenicity). The performance of ADMET predictor results was assessed. The work presented here proposes a computationally driven strategy for designing and discovering a new sulfonamide scaffold for bacterial inhibition.

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“…In recent years, extensive research efforts have been dedicated to synthesizing various series of chromene compounds, unveiling their exceptional potential in addressing a wide range of medical conditions and enhancing their biological effectiveness [10]. These applications include antibacterial [11,12], anticancer [13,14], anticholinesterase [15], antidepressant [16], antidiabetic [17], antiepileptic [18], antifungal [19], anti-gastric cancer [20], anti-HIV [21], antihypertensive [22], anti-inflammatory [23], antimalarial [24], antioxidant [25][26][27], antiproliferative [28], antituberculosis [29], and antivascular [30] applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of a New Class of Chromene-Azo Sulfonamide Hybrids as Promising Anticancer Candidates with the Exploration of Their EGFR, hCAII, and MMP-2 Inhibitors Based on Molecular Docking Assays

Alblewi,

Alsehli,

Hritani

et al. 2023

IJMS

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In this study, novel selective antitumor compounds were synthesized based on their fundamental pharmacophoric prerequisites associated with EGFR inhibitors. A molecular hybridization approach was employed to design and prepare a range of 4H-chromene-3-carboxylates 7a–g, 8, and 11a–e derivatives, each incorporating a sulfonamide moiety. The structures of these hybrid molecules were verified using comprehensive analytical and spectroscopic techniques. During the assessment of the newly synthesized compounds for their anticancer properties against three tumor cell lines (HepG-2, MCF-7, and HCT-116), compounds 7f and 7g displayed remarkable antitumor activity against all tested cell lines, outperforming the reference drug Cisplatin in terms of efficacy. Consequently, these promising candidates were selected for further investigation of their anti-EGFR, hCAII, and MMP-2 potential, which exhibited remarkable effectiveness against EGFR and MMP2 when compared to Sorafenib. Additionally, docking investigations regarding the EGFR binding site were implemented for the targeted derivatives in order to attain better comprehension with respect to the pattern in which binding mechanics occur between the investigated molecules and the active site, which illustrated a higher binding efficacy in comparison with Sorafenib.

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A facile one-pot green synthesis of novel 2-amino-4H-chromenes: antibacterial and antioxidant evaluation

Cited by 8 publications

References 46 publications

2‐Aminopyrazine catalyzed three‐component and one‐pot construction of 2‐amino‐4H‐chromene‐3‐carbonitrile by mortar‐pestle grinding and molecular docking studies

2‐Aminopyrazine catalyzed three‐component and one‐pot construction of 2‐amino‐4H‐chromene‐3‐carbonitrile by mortar‐pestle grinding and molecular docking studies

Evaluation of antibacterial, cytotoxicity, and apoptosis activity of novel chromene-sulfonamide hybrids synthesized under solvent-free conditions and 3D-QSAR modeling studies

Synthesis and Characterization of a New Class of Chromene-Azo Sulfonamide Hybrids as Promising Anticancer Candidates with the Exploration of Their EGFR, hCAII, and MMP-2 Inhibitors Based on Molecular Docking Assays

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