3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

Abdou, Moaz M.; Abu‐Rayyan, Ahmed; Bedir, Ahmed G.; Abdel-Fattah, Sherif A.; Omar, A. M. A.; Ahmed, Asmaa A.; El‐Desoky, El‐Sayed I.; Ghaith, Eslam A.

doi:10.1039/d1ra05574g

Cited by 11 publications

(9 citation statements)

References 180 publications

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“…Given those mentioned above and in follow-up, our longstanding interest in the preparation and reactions of 1,3-diketones and their implementations, − the purpose of this study was to inspect the multidimensional insights of the synthesized pyrazoles as corrosion inhibitors and assess their inhibition efficiency on C-steel via some electrochemical measurements such as open circuit potential (OCP), potentiodynamic polarization (PP), and electrochemical impedance spectroscopy (EIS). The two synthesized pyrazoles’ potential inhibitory mechanisms on C-steel corrosion were investigated using density functional theory (DFT) and Monte Carlo (MC) simulations.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Investigation of C-Steel Corrosion Inhibition, In Silico, and Sulfate-Reducing Bacteria Investigations Using Pyrazole Derivatives

Shaban,

El Basiony,

Radwan

et al. 2023

ACS Omega

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The inhibitory impact of the two synthesized pyrazole derivatives (3 and 4) toward metallic and microbial corrosion was investigated. Using open circuit potential, potentiodynamic polarization, and electrochemical impedance spectroscopy, it was possible to determine their ability to prevent the corrosion of C-steel in 1 M HCl, which was significantly enhanced with increasing concentration (ex. 93%). They act as mixed-type inhibitors, according to polarization curves. The compounds under investigation were adsorbed on a C-steel surface in 1 M HCl following the Langmuir isotherm model. The double-layer capacitance was decreased, and the charge transfer resistance (R ct) was raised due to the examined inhibitors’ adsorption. Investigating changes in the surface morphology and confirming the corrosion inhibition mechanism are done using scanning electron microscopy. Density functional theory calculations and Monte Carlo simulations were also conducted to show the adsorption affinity of the understudied compounds over the steel substrate in neutral and protonated forms. Furthermore, the antimicrobial performance of the two synthesized pyrazoles against sulfate-reducing bacteria was evaluated, and the recorded inhibition efficiency was 100%. The current research shows important developments in producing highly effective anticorrosion and antimicrobial pyrazole derivatives.

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Section: Introductionmentioning

confidence: 99%

Electrochemical Investigation of C-Steel Corrosion Inhibition, In Silico, and Sulfate-Reducing Bacteria Investigations Using Pyrazole Derivatives

Shaban,

El Basiony,

Radwan

et al. 2023

ACS Omega

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“…Aromatic compounds, especially coumarin derivatives, frequently display several weak bands in the range of 3100-3000 cm À 1 because of aromatic CÀ H stretching vibrations. [3,9,18,27] The range of the CÀ H in-plane bending oscillations is between 1500 and 1100 cm À 1 , while the range of the CÀ H out-of-plane bending oscillations is around 1000 to 675 cm À 1 . [3,9,18,27] The CÀ H stretching oscillations' identifying bands are located in ATC at 3140, 3100, 3060, 3056, 3052, 3051, 3050, 3037, 3027, and 3017 cm À 1 for Conf 1 and 3138, 3074, 3060, 3054, 3053, 3050, 3048, 3037, 3028, and 3025 cm À 1 for Conf 2, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…3‐(bromoacetyl) coumarins are considered starting materials in the synthesis of bioactive derivatives [8] . They are also important compounds with various biological activities such as antiproliferative, antimicrobial, etc [9] …”

Section: Introductionmentioning

confidence: 99%

“…[8] They are also important compounds with various biological activities such as antiproliferative, antimicrobial, etc. [9] The most significant types of vibrational spectroscopy are mid-infrared (IR), near-IR, and Raman spectroscopy. Both are intelligible, typical elementary vibration techniques that are employed for the lighting of molecular structures.…”

Section: Introductionmentioning

confidence: 99%

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Determining Stable Structure and in Vitro Antiproliferative Properties of a Novel 3‐(2‐((4‐Trifluoromethyl)phenyl)amino)thiazol‐4‐yl)‐2H‐chromen‐2‐one Molecule

Burak Sarigüney,

Karakaş Sarikaya,

Pehlivanoğlu

2023

Chemistry & Biodiversity

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Since coumarin and thiazole derivatives are known to have antioxidant properties, a novel derivative was synthesized in this article. 3‐(2‐((4‐(trifluoromethyl)phenyl)amino)thiazol‐4‐yl)‐2H‐chromen‐2‐one (ATC) was synthesized as a novel compound with high yield and characterized by Raman, FT‐IR, 13C‐NMR, and 1H‐NMR spectroscopic procedures and DFT calculations. In this study, the potential in vitro antiproliferative properties of the ATC compound were evaluated on colorectal cancer (HT29) and melanoma (SK‐MEL‐30) cell lines. According to the results, the compound was found to be significantly active, approximately 2.6‐fold, against melanoma cells compared to healthy fibroblast (L929) cells. Unlike melanoma cells, the compound did not have any adverse effects on colorectal cancer cells. Due to these findings, the compound can be harnessed as a promising antiproliferative drug candidate for preclinical studies against melanoma.

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“…This bond is reactive and chemically available; hence, it is possible to obtain coumarins modified at C-3 and C-4 and even larger fused coumarin heterocyclic derivatives. The Kumada, Stille, Heck, Sonogashira, Negishi, Suzuki, or Buchwald-Hartwig coupling reactions are most often used for this purpose [55][56][57][58][59][60][61][62][63]. The substrates in the abovementioned reactions are mostly coumarin derivatives such as vinyl coumarin, bromocoumarin, coumarin-3-carboxylic acid, or triflate-substituted coumarin.…”

Section: Scheme 3 Direct Synthesis Of Coumarins By C-h Bond Activatio...mentioning

confidence: 99%

Coumarins Synthesis and Transformation via C–H Bond Activation—A Review

Szwaczko

2022

Inorganics

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For several decades, coumarins have attracted considerable attention due to the fact of their application in diverse fields such as medical science and biomedical research as well as several industrial branches. Recently, many compounds containing the coumarin moiety have been intensively studied, mainly due to the fact of their biological activities such as antitumor, antioxidative, anti-HIV, vasorelaxant, antimicrobial, and anticancer. They are also widely used as fluorescent dyes and probes because of their great structural flexibility and large fluorescent quantum yields. For this reason, numerous attempts have been made to develop new and more practical methods for the synthesis of these compounds. This review aims at providing a comprehensive overview of coumarin synthesis methods by direct C–H bond activation in order to demonstrate the current state-of-the-art methods as well as the current limitations.

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3-(Bromoacetyl)coumarins: unraveling their synthesis, chemistry, and applications

Abstract: This review emphasizes recent developments in synthetic routes of 3-(bromoacetyl)coumarin derivatives.

Cited by 11 publications

References 180 publications

Electrochemical Investigation of C-Steel Corrosion Inhibition, In Silico, and Sulfate-Reducing Bacteria Investigations Using Pyrazole Derivatives

Electrochemical Investigation of C-Steel Corrosion Inhibition, In Silico, and Sulfate-Reducing Bacteria Investigations Using Pyrazole Derivatives

Determining Stable Structure and in Vitro Antiproliferative Properties of a Novel 3‐(2‐((4‐Trifluoromethyl)phenyl)amino)thiazol‐4‐yl)‐2H‐chromen‐2‐one Molecule

Coumarins Synthesis and Transformation via C–H Bond Activation—A Review

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