Microwave‐assisted Synthesis, Characterization, and Density Functional Theory Study of Biologically Active Ferrocenyl Bis‐pyrazoline and Bis‐pyrimidine as Organometallic Macromolecules

Khan, Salman A.; Asiri, Abdullah M.; Zayed, Mohie E. M.; Parveen, Humaira; Aqlan, Faisal M.; Sharma, Kamlesh

doi:10.1002/jhet.3381

Cited by 21 publications

(7 citation statements)

References 24 publications

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“…14 Several studies have reported the synthesis of bis-pyrazolines and bis-pyrimidines from bis-chalcones using microwave heating and ultrasound irradiation. [15][16][17] We here report the design and synthesis of three new bis-heterocyclic compounds from a bis-chalcone that was prepared by the reaction between acetophenone and terephthalaldehyde using the Claisen-Schmidt method. The title compounds were tested and their antimicrobial activities on three bacteria and two types of fungi were studied.…”

Section: Introductionmentioning

confidence: 99%

New bis-heterocyclic structures: Synthesis, characterization and biological activity

Farhan,

Al-Jumaili,

Bakr

2023

Journal of Chemical Research

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New bis-heterocyclic compounds were synthesized by reacting two moles of isoniazid, cyanoguanidine and 2-aminophenol with one mole of a bis-chalcone. The bis-chalcone was prepared from the reaction between acetophenone and terephthalaldehyde using sodium hydroxide. All the prepared compounds were purified and their structures confirmed by spectroscopic methods, such as Fourier transform infrared, 1H NMR and 13C NMR. Their effect against three types of bacteria (negative and positive) for gram stain Escherichia coli, Klebsiella pneumoniae and Staphylococcus aureus was studied and discussed. The results obtained were compared with those of gentamicin, chloramphenicol and amikacin. Our new compounds showed clear inhibition of the different bacteria types with some of them exceeding the effects of the drugs possibly due to the bis-heterocyclic structures of our compounds. The effects of our compounds on the growth of certain types of fungi, Trichophyton and Aspergillus, were studied, showing inhibition of the growth of these fungi at high concentrations.

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Section: Introductionmentioning

confidence: 99%

New bis-heterocyclic structures: Synthesis, characterization and biological activity

Farhan,

Al-Jumaili,

Bakr

2023

Journal of Chemical Research

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“… 11 Additionally, molecules that contain more than one pyrimidine core have been reported to act as antibacterial and antifungal agents. 12 , 13 …”

Section: Introductionmentioning

confidence: 99%

“…Pyrimidines have been used as suitable starting materials for the synthesis of novel scaffolds that are parent to DNA bases and derivatives, thus targeting compounds with relevant biological and pharmacological properties. − For example, trihalomethyl-substituted pyrimidines have been used as caspase inhibitors, hepatitis C inhibitors, , antiplasmodials, NTPDase inhibitors, as well as anticancer agents . Additionally, molecules that contain more than one pyrimidine core have been reported to act as antibacterial and antifungal agents. , …”

Section: Introductionmentioning

confidence: 99%

“…11 Additionally, molecules that contain more than one pyrimidine core have been reported to act as antibacterial and antifungal agents. 12,13 There have been several studies regarding the chemoselectivity between N-and O-alkylation 14−19 (or S-alkylation in pyrimidine-2(1H)-thiones 20−22 ) when preparing alkyl/aryl derivatives; however, directing the reaction toward furnishing one sole product in the absence of protecting groups or specific catalysts is a problem yet to overcome. 23 More specifically, several derivatization techniques have already been reported for the synthesis of trifluoromethyl-containing pyrimidines; 24−28 however, the most widely explored one is still alkylation using alkyl halides or esters, 29 and others are based on the application of TMS-protected pyrimidines, 29 cyclocondensation strategies using starting materials that allow the desired substitution pattern, 30−32 and copper-mediated coupling reactions with aryl boronic acids.…”

Section: ■ Introductionmentioning

confidence: 99%

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Chemoselective O-Alkylation of 4-(Trifluoromethyl)pyrimidin-2(1H)-ones Using 4-(Iodomethyl)pyrimidines

et al. 2022

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This study reports two strategies for preparing O -alkyl derivatives of 6-substituted-4-(trifluoromethyl)pyrimidin-(1 H )-ones: a linear protocol of alkylation, using a CCC -building block followed by [3 + 3]-type cyclocondensation with 2-methylisothiourea sulfate and a convergent protocol based on direct alkylation, using 4-(iodomethyl)-2-(methylthio)-6-(trihalomethyl)pyrimidines. It was found that the cyclocondensation strategy is not feasible; thus, the direct chemoselective O -alkylation was performed, and 18 derivatives of the targeted pyrimidines were obtained in 70–98% yields. The structure of the products was unambiguously determined via single crystal X-ray analyses and two-dimensional nuclear magnetic resonance experiments.

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“…Recently, microwave assisted reactions has arisen as one of the most convenient and reproducible methods for synthesis of various heterocyclic compounds due to its green and sustainable nature. In view of this, a number of authors have reported the microwave-assisted synthesis of various organic compounds, which have been widely applied in the drug discovery field, due to enhanced reaction rates, high yields, improved purity, and greener reaction condition [2,3,4,5,6].…”

Section: Introductionmentioning

confidence: 99%

Green Accelerated Synthesis, Antimicrobial Activity and Seed Germination Test of Quaternary Ammonium Salts of 1,2-bis(4-pyridyl)ethane

et al. 2019

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A family of fifteen quaternary ammonium salts (QAs), bearing the 1,2-bis(4-pyridyl)ethane core, were obtained using for the first time two different green methods, such as microwave (MW) and ultrasounds (US) irradiation, with very good yields and in much shorter times compared to the classical method, and an assay on their antimicrobial action against Escherichia coli (E. coli) was carried out. While 12 to 24 hours were required for complete alkylation of 1,2-bis(4-pyridyl)ethane by reactive halogenated derivatives in anhydrous solvent under reflux conditions, MW and US irradiation reduced the reaction time and the desired products were achieved in a few min. One of the aims of this study was to evaluate the antibacterial potential of the synthesized QAs against pathogenic bacteria, along with their impact on germination activity of wheat seeds (Triticum aestivum L.). The antibacterial activity of the QAs against Escherichia coli was explored by determining the minimum inhibitory concentration (MIC). The MIC values varied from 0.312 to 2.5 mg/mL, highlighting the lowest values attained for the derivatives containing methoxy, chlorine and benzofurane functional groups. The viability of aerobic bacteria was determined with the Tetrazolium/Formazan Test, a method that was found to be the best alternative approach with respect to the difuzimetric method. Seeds of Triticum aestivum L. were used for the evaluation of the germination indicators, such as seed germination (SG), the relative seed germination (RSG), the relative radicle growth (RRG), and the seed germination index (GI). The toxicity studies of QAs 1, 4 and 7, at two different concentrations, showed no inhibitory effect on seed germination.

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Microwave‐assisted Synthesis, Characterization, and Density Functional Theory Study of Biologically Active Ferrocenyl Bis‐pyrazoline and Bis‐pyrimidine as Organometallic Macromolecules

Cited by 21 publications

References 24 publications

New bis-heterocyclic structures: Synthesis, characterization and biological activity

New bis-heterocyclic structures: Synthesis, characterization and biological activity

Chemoselective O-Alkylation of 4-(Trifluoromethyl)pyrimidin-2(1H)-ones Using 4-(Iodomethyl)pyrimidines

Green Accelerated Synthesis, Antimicrobial Activity and Seed Germination Test of Quaternary Ammonium Salts of 1,2-bis(4-pyridyl)ethane

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