One pot synthesis of thiazolo[2,3-b]dihydropyrimidinone possessing pyrazole moiety and evaluation of their anti-inflammatory and antimicrobial activities

Viveka, S.; Dinesha,; Nagaraja, G. K.; Shama, Prasanna; Basavarajaswamy, Guru; Rao, K. Poornachandra; Sreenivasa, M. Y.

doi:10.1007/s00044-017-2058-8

Cited by 22 publications

(12 citation statements)

References 41 publications

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“…Compound 1 was synthesized through one-pot three component Biginelli reaction [ 50 , 51 ] using an indole-3-carbaldehyde, ethyl acetoacetate, and thiourea. The mixture was stirred under reflux in ethanol containing few drops of 37% HCl.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Molecular Modeling and Antitumor Evaluation of Novel Indolyl-Pyrimidine Derivatives with EGFR Inhibitory Activity

et al. 2021

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Scaffolds hybridization is a well-known drug design strategy for antitumor agents. Herein, series of novel indolyl-pyrimidine hybrids were synthesized and evaluated in vitro and in vivo for their antitumor activity. The in vitro antiproliferative activity of all compounds was obtained against MCF-7, HepG2, and HCT-116 cancer cell lines, as well as against WI38 normal cells using the resazurin assay. Compounds 1–4 showed broad spectrum cytotoxic activity against all these cancer cell lines compared to normal cells. Compound 4g showed potent antiproliferative activity against these cell lines (IC50 = 5.1, 5.02, and 6.6 μM, respectively) comparable to the standard treatment (5-FU and erlotinib). In addition, the most promising group of compounds was further evaluated for their in vivo antitumor efficacy against EAC tumor bearing mice. Notably, compound 4g showed the most potent in vivo antitumor activity. The most active compounds were evaluated for their EGFR inhibitory (range 53–79 %) activity. Compound 4g was found to be the most active compound against EGFR (IC50 = 0.25 µM) showing equipotency as the reference treatment (erlotinib). Molecular modeling study was performed on compound 4g revealed a proper binding of this compound inside the EGFR active site comparable to erlotinib. The data suggest that compound 4g could be used as a potential anticancer agent.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Molecular Modeling and Antitumor Evaluation of Novel Indolyl-Pyrimidine Derivatives with EGFR Inhibitory Activity

et al. 2021

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“…The compounds 92a (85.33), 92d (81.32), and 92h (80.75) showed potent anti-inflammatory activity compared with the other test compounds and are comparable with the standard, indomethacin (86.76). This emphasizes the presence of the 3F-4CH 3 - substituted phenyl ring on the 5th position of the 3-oxothiazolopyrimidine nucleus in this pyrazole series [ 101 ]. Additionally, El-Emary et al found that compounds 110b and 112b ( Scheme 29 ) had the most anti-inflammatory activity, comparable to that of Indomethacin [ 113 ].…”

Section: Anti-inflammatory Activity Of Antimicrobial Pyrimidine Derivativesmentioning

confidence: 94%

“…Viveka et al reported the Biginelli synthesis of 3,4-dihydropyrimidinones 90a – 90c . Reaction of each compound 90 with pyrazole 91 gave thiazolo[2,3-b] dihydropyrimidinones 92a – 92c ( Scheme 23 ) [ 101 ]. As observed in Table 5 , compounds 92a – 92c show good antibacterial activity against all the tested species (MIC = 3.12–25 μg mL −1 ).…”

Section: Biginelli Reaction Mediated Synthesis Of Antimicrobial Pyrimidine Derivativesmentioning

confidence: 99%

Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties

Marinescu

2021

Molecules

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Antimicrobial resistance was one of the top priorities for global public health before the start of the 2019 coronavirus pandemic (COVID-19). Moreover, in this changing medical landscape due to COVID-19, finding new organic structures with antimicrobial and antiviral properties is a priority in current research. The Biginelli synthesis that mediates the production of pyrimidine compounds has been intensively studied in recent decades, especially due to the therapeutic properties of the resulting compounds, such as calcium channel blockers, anticancer, antiviral, antimicrobial, anti-inflammatory or antioxidant compounds. In this review we aim to review the Biginelli syntheses reported recently in the literature that mediates the synthesis of antimicrobial compounds, the spectrum of their medicinal properties, and the structure–activity relationship in the studied compounds.

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“…Dihydropyrimidinones are heterocyclic compounds synthesized by simple multi-component reactions such as the Biginelli reaction with a variety of methodologies [19,20]. Dihydropyrimidinones have been identified to possess a wide range of applications in pharmacology and medicinal chemistry including anticancer [21], antiinflammatory [22], antimicrobial [23], antidiabetic, and antioxidant agents [24]. is skeleton also showed a broad spectrum of biological activities including calcium channel antagonism/inhibition, Eg5 kinesin, and topoisomerase I inhibitor [25].…”

Section: Introductionmentioning

confidence: 99%

Rational Design, Synthesis, In Vitro, and In Silico Studies of Dihydropyrimidinone Derivatives as β-Glucuronidase Inhibitors

Karimian

Moghdani

Khoshneviszadeh

et al. 2021

Journal of Chemistry

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In the current study, a series of dihydropyrimidinone derivatives were rationally designed as β-glucuronidase inhibitors. These designed compounds were successfully synthesized and characterized through various spectroscopic techniques such as IR, 1H-NMR, 13C-NMR, and EI-MS. A structure-activity relationship (SAR) of synthesized derivatives to inhibit β-glucuronidase was also established. In vitro biological evaluations revealed that 4i as the most potent compound in this series has an IC50 value of 31.52 ± 2.54 μM compared to the standard D-saccharic acid 1,4-lactone (IC50 = 41.32 ± 1.82 µM). Also, molecular docking and dynamics studies of the most potent compound are performed to evaluate interactions between the active compound and binding site.

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One pot synthesis of thiazolo[2,3-b]dihydropyrimidinone possessing pyrazole moiety and evaluation of their anti-inflammatory and antimicrobial activities

Cited by 22 publications

References 41 publications

Design, Synthesis, Molecular Modeling and Antitumor Evaluation of Novel Indolyl-Pyrimidine Derivatives with EGFR Inhibitory Activity

Design, Synthesis, Molecular Modeling and Antitumor Evaluation of Novel Indolyl-Pyrimidine Derivatives with EGFR Inhibitory Activity

Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties

Rational Design, Synthesis, In Vitro, and In Silico Studies of Dihydropyrimidinone Derivatives as β-Glucuronidase Inhibitors

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