Synthesis and antimicrobial evaluation of novel substituted pyrimidine scaffold

Ghodasara, H.B.; Trivedi, Anjali; Kataria, Vipul B.; Patel, Bankim; Shah, V. H.

doi:10.1007/s00044-013-0596-2

Cited by 12 publications

(5 citation statements)

References 17 publications

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“…In the current study, Biginelli type reaction was utilized for the synthe sis of substituted pyrimidine derivatives [24,25]. According to the recent report by Ghodasara et al [17], several derivatives of 6 amino 4 phenyl 2 thioxo 1,2,3,4 tetrahydropyrimidine 5 carboni triles were prepared by one pot and three compo nent reaction between aryladehydes, malononi trile, and thiourea in EtOH in the presence of sodium ethoxide at room temperature as shown in Scheme.…”

Section: Resultsmentioning

confidence: 99%

“…Thio substituted pyrimidine derivatives occupy a special position among these compounds. They are also identified as potential antimicrobial and antican cer [11][12][13][14][15][16][17][18], as well as anti inflammatory agents [19]. Prompted by these reports and in continuation of our endeavor on potential anticancer agents [20,21], we have now focused our attention on preparing a series of 6 amino 4 phenyl 2 thioxo 1,2,3,4 tetrahydro pyrimidine 5 carbonitriles (I)-(X) and screened them for antiproliferative activity against human breast cancer (MCF 7), human colon carcinoma (HT29), and non malignant mouse fibroblast (L929) cell lines.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and evaluation of cytotoxicity of 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles

et al. 2016

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Several derivatives of 6 amino 4 aryl 2 thioxo 1,2,3,4 tetrahydropyrimidine 5 carbonitriles were synthesized via Biginelli type reaction and tested for their anti proliferative activity on human breast cancer (MCF 7) and human colon carcinoma (HT29) cell lines. Malignant and non malignant cells were cultivated in RPMI medium and incubated with different concentrations of these pyrimidines. Cell viability was evaluated by MTT assay. Apoptotic cells were determined using DAPI (4' 6 diamidino 2 phenylindole) and propidium iodide staining of DNA fragmentation by flow cytometry (sub G1 peak). 6 Amino 4 (4 chlorophenyl) 2 thioxo 1,2,3,4 tetrahydropyrimidine 5 carbonitrile and 6 amino 4 [4 dimethy lamino)phenyl] 2 thioxo 1,2,3,4 tetrahydropyrimidine 5 carbonitrile decreased the viability of MCF 7 and HT29 cells, in contrast to L929 cells. These compounds induced a sub G1 peak inflow cytometry histo grams of treated cells indicating that apoptosis is involved in their toxicity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of cytotoxicity of 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles

et al. 2016

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“…The reaction took place in THF under microwave irradiation to provide excellent yields of the nitro-DHPMs 122 (Scheme 52). A Biginelli-type three-component reaction was developed by Shah et al for the synthesis of a new family of pyrimidine derivatives [127]; they used malononitrile 123 as the keto ester component, thiourea 1, and aromatic aldehydes 2 in refluxing methanol. Resulting DMHPs 124 were treated with dimethyl sulfate and oxidized to the corresponding pyrimidines 125 in good yields; these compounds display interesting antibacterial activities (Scheme 53).…”

Section: Other Different Substrates As the Keto Ester Componentmentioning

confidence: 99%

“…The heating of the three-component mixture with the base in DMF at 90 • C provided the corresponding DHMPs 127 unsubstituted at position 6 (Scheme 54); it is noteworthy that this substitution is difficult to access with regular Biginelli conditions. thesis of a new family of pyrimidine derivatives [127]; they used malononitrile 123 as the keto ester component, thiourea 1, and aromatic aldehydes 2 in refluxing methanol. Resulting DMHPs 124 were treated with dimethyl sulfate and oxidized to the corresponding pyrimidines 125 in good yields; these compounds display interesting antibacterial activities (Scheme 53).…”

Section: Other Different Substrates As the Keto Ester Componentmentioning

confidence: 99%

Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions

et al. 2022

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The interest in 3,4-dihydropyrimidine-2(1H)-(thio)ones is increasing every day, mainly due to their paramount biological relevance. The Biginelli reaction is the classical approach to reaching these scaffolds, although the product diversity suffers from some limitations. In order to overcome these restrictions, two main approaches have been devised. The first one involves the modification of the conventional components of the Biginelli reaction and the second one refers to the postmodification of the Biginelli products. Both strategies have been extensively revised in this manuscript. Regarding the first one, initially, the modification of one of the components was covered. Although examples of modifications of the three of them were described, by far the modification of the keto ester counterpart was the most popular approach, and a wide variety of different enolizable carbonylic compounds were used; moreover, changes in two or the three components were also described, broadening the substitution of the final dihydropyrimidines. Together with these modifications, the use of Biginelli adducts as a starting point for further modification was also a very useful strategy to decorate the final heterocyclic structure.

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“…Ghodasara et al reported the synthesis of Biginelli compounds 43a – 43d , the corresponding methylated derivatives 44a – 44d , and their oxidized compounds 45a – 45d ( Scheme 13 ) [ 83 ]. The preliminary in vitro biological activities of the compounds revealed that compounds 43a , 44d , 45h , and 45j exhibited significant (maximum) antibacterial activities against all bacterial tested strains, S. aureus MTCC 96, E. coli MTCC 443, and B. subtilis MTCC 441, compared with Ampicillin, Chloramphenicol, Ciprofloxacin, and Norfloxacin as standards drug, and against both fungal strains, C. albicans MTCC 227 and A. niger MTCC 282.…”

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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Synthesis and antimicrobial evaluation of novel substituted pyrimidine scaffold

Cited by 12 publications

References 17 publications

Synthesis and evaluation of cytotoxicity of 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles

Synthesis and evaluation of cytotoxicity of 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles

Synthesis of 3,4-Dihydropyrimidin(thio)one Containing Scaffold: Biginelli-like Reactions

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

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