Synthesis of arylidene hydrazinylpyrido[2,3-d]pyrimidin-4-ones as potent anti-microbial agents

Abdelhameed, Reda M.; Darwesh, Osama M.; El‐Shahat, Mahmoud

doi:10.1016/j.heliyon.2020.e04956

Cited by 29 publications

(22 citation statements)

References 54 publications

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“…To examine the SAR studies [ 27 , 28 ]: Electron withdrawing group (-Cl) on the quinoline ring of 5f showed maximum antibacterial activity than other imidazoquinolines and reached the effectiveness of the standard. At high concentration (100 mg/disc), 5f demonstrated the higher activity against E. coli, K. pneumonia, S. paratyphi, S. typhi, M. butyricum than that of in standard (10 mg/disc).…”

Section: Resultsmentioning

confidence: 99%

Synthesis, antibacterial, anti-oxidant and molecular docking studies of imidazoquinolines

Velmurugan

Don

Kannan

et al. 2021

Heliyon

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Quinoline and imidazole derivatives have been playing a significant role in functional bioactivities and were potentially used as antibacterial, antifungal, anticancer, and anti-inflammatory drugs. Owing to the limitation of drug resistance, herein we synthesized thio-, chloro-, and hydroxyl-functionalized various imidazoquinolines by molecular hybridization approach. All the imidazoquinoline derivatives were examined for their antibacterial activity against selected bacterial pathogens by the agar well diffusion method. In addition, the anti-oxidant efficacy of imidazoquinolines was also tested using ferric reducing antioxidant power (FRAP). Among them, electron-withdrawing (-Cl) substituent containing imidazoquinoline 5f showed higher antibacterial and antioxidant activities than other imidazoquinolines and reached the effectiveness of the standard. In addition, compounds 4f, 5e, and 3f showed moderate antibacterial activity and other derivatives displayed weak activity against various pathogens. Molecular docking studies were also performed on selected imidazoquinoline derivatives (3f, 4f, and 5f), which showed high docking score and strong binding energy values. These results revealed that thio-imidazoquinoline could assist as a prototype for the designing of multidrug-resistant antibiotics against various microbial organisms.

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Section: Resultsmentioning

confidence: 99%

Synthesis, antibacterial, anti-oxidant and molecular docking studies of imidazoquinolines

Velmurugan

Don

Kannan

et al. 2021

Heliyon

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“…Characterizations of the produced biosynthesized FeNPs were done using High-resolution transmission electron microscopy (HRTEM) (JEOL 2100 Japan, at National Research Centre (NRC), Cairo, Egypt) to define the size and shape of the produced biosynthesized nanostructures [25,26]. The samples were prepared by drop-coating of FeNPs solutions onto the carbon-coated copper grid which loaded onto a specimen holder after drying.…”

Section: Morphological Characterization Of Fenps Using Transmission Electron Microscopy (Tem)mentioning

confidence: 99%

“…Inoculum was prepared by suspending a loop full of bacterial cultures into 10 ml of nutrient agar broth and incubated at 37 ˚C for 24 h. About 60 μl of bacterial suspensions adjusted to 10 6 -10 7 CFU/ml were taken and poured into Petri plates containing 25 ml sterilized nutrient agar medium. Method of well diffusion was applied in this procedure according to the previous illustrated by Abdelhameed et al [25]. Different concentrations (12.50, 14.28, 16.67, 20.00, 25.00, 33.30, 50, 10, 133.33, 200.00 and 266.60 mg/ml) of biosynthesized FeNPs suspended into sterilized ddH2O were prepared and 50 µl of them were added individually to the wells.…”

Section: Application Of the Biosynthesized Fenps For Municipal Wastewater Remediationmentioning

confidence: 99%

Nano-Bioremediation of Municipal Wastewater Using Myco-Synthesized Iron Nanoparticles

et al. 2021

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Metal nanostructures have potential effective impacts with many arenas like catalysis, sensors, optics, electronics, functional materials, environment and medicine. Thus, iron nanoparticles (FeNPs) were mycogenic synthesized in this study as effective antimicrobial agent and heavy metals removers. The isolation of 37 fungi were done from contaminated 10 soil (with iron ions or metals) samples and they screened. The most powerful fungal isolate was Fusarium oxysporum. Biosynthesized FeNPs size were 0.7 to 3 nm (high small size) with spherical shape based on TEM analysis. However, XRD, FT-IR analyses confirmed that characterization and led to form iron at zero valent. The obtained FeNPs were used as antibacterial agent against broad spectrum of environmental pathogens with minimum amounts (about 20 µg/ml) compared with reference antibiotics. This drive for using it to control microbial pathogens through municipal wastewater. For its high adsorption activity, it is used for removing heavy metals from their contaminated wastewater.

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“…Pyrido [2,3-d]pyrimidine is one of the most privileged heterocyclic frameworks in several efficacious pharmacological compounds. Pyrido [2,3-d]pyrimidine ring systems have assorted biological and pharmacological activities such as being analgesic, anti-inflammatory [1-3], antitubercular [4], antimicrobial [5][6][7], a threonine tyrosine kinase (TTK) inhibitor [8], an adenosine kinase inhibitor [9], antiviral [10], antioxidant [11][12][13][14], a dihydrofolate reductase inhibitor [15,16], and an efficient glucosidase inhibitor [17,18]. Moreover, the 1,3-benzothiazole nucleus is a highly significant scaffold in the drug design, due to important pharmacological and medicinal activities, such as being antiviral [19], antituberculosis [20], an identifier of selective CB2 receptor ligands [21], antitumor [22][23][24], antimicrobial [25][26][27], anticonvulsant [28], a schistosome BCL-2 inhibitor [29], antidiabetic [30], antioxidant [31], an anti-Alzheimer drug [32] and a urease inhibitor [33] among the heterocyclic compounds containing a pyrimidine and benzothiazole nucleus that exhibits biological activity [34][35][36] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis

et al. 2022

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In our attempt towards the synthesis and development of effective antimicrobial, anticancer and antioxidant agents, a novel series of 2,3-dihydropyrido[2,3-d]pyrimidin-4-one 7a–e and pyrrolo[2,1-b][1,3]benzothiazoles 9a–e were synthesized. The synthesis of 2-(1,3-benzo thiazol-2-yl)-3-(aryl)prop-2-enenitrile (5a–e) as the key intermediate was accomplished by a microwave efficient method. Via a new variety oriented synthetic microwave pathway, these highly functionalized building blocks allowed access to numerous fused heteroaromatic such as 7-amino-6-(1,3-benzo thiazol-2-yl)-5-(aryl)-2-thioxo-2,3dihydropyrido [2,3-d]pyrimidin-4(1H)-one 7a–e and 1-amino-2-(aryl)pyrrolo[2,1-b][1,3]benzothiazole-3-carbonitrile derivatives 9a–e in order to study their antimicrobial and anticancer activity. The present investigation offers effective and rapid new procedures for the synthesis of the newly polycondensed heterocyclic ring systems. All the newly synthesized compounds were evaluated for antimicrobial, anticancer and antioxidant activity. Compounds 7a,d, and 9a,d showed higher antimicrobial activity than cefotaxime and fluconazole while the remaining compounds exhibited good to moderate activity against bacteria and fungi. An anticancer evaluation of the newly synthesized compounds against the three tumor cell lines (lung cell NCI-H460, liver cancer HepG2 and colon cancer HCT-116) exhibited that compounds 7a, d, and 9a,d have higher cytotoxicity against the three human cell lines compared to doxorubicin as a reference drug. These compounds also exhibited higher antioxidant activity and a great ability to protect DNA from damage induced by bleomycin.

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Synthesis of arylidene hydrazinylpyrido[2,3-d]pyrimidin-4-ones as potent anti-microbial agents

Cited by 29 publications

References 54 publications

Synthesis, antibacterial, anti-oxidant and molecular docking studies of imidazoquinolines

Synthesis, antibacterial, anti-oxidant and molecular docking studies of imidazoquinolines

Nano-Bioremediation of Municipal Wastewater Using Myco-Synthesized Iron Nanoparticles

Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis

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