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Keywords = 6-chlorouracil

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9 pages, 369 KB  
Proceeding Paper
Synthesis of Amidines and Its Application to Pyrimidouracil Synthesis
by Pradip Debnath
Chem. Proc. 2021, 3(1), 132; https://doi.org/10.3390/ecsoc-24-08503 - 20 Nov 2020
Viewed by 5875
Abstract
An efficient and sustainable copper-catalyzed protocol has been developed for the preparation of amidines via nucleophilic addition of amines into nitriles. The reaction proceeded smoothly at 100 °C in the presence of CuCl, Cs2CO3, and 2,2/-bipyridine under [...] Read more.
An efficient and sustainable copper-catalyzed protocol has been developed for the preparation of amidines via nucleophilic addition of amines into nitriles. The reaction proceeded smoothly at 100 °C in the presence of CuCl, Cs2CO3, and 2,2/-bipyridine under oxygen (O2) atmosphere in 2,2,2-trifluoroethanol (TFE) solvent. Moreover, a straightforward synthetic method for the synthesis of substituted pyrimidouracils via PhI(OAc)2-mediated oxidative coupling of N-uracil amidines and methylarenes has been developed. The starting materials N-uracil amidines were synthesized from 6-chlorouracil and amidines via nucleophilic substitution reactions. Full article
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23 pages, 3675 KB  
Article
Novel Isoxazolidine and γ-Lactam Analogues of Homonucleosides
by Dorota G. Piotrowska, Iwona E. Głowacka, Dominique Schols, Robert Snoeck, Graciela Andrei and Joanna Gotkowska
Molecules 2019, 24(22), 4014; https://doi.org/10.3390/molecules24224014 - 6 Nov 2019
Cited by 15 | Viewed by 3695
Abstract
Homonucleoside analogues cis-16 and trans-17 having a (5-methoxycarbonyl)isoxazolidine framework were synthesized via the 1,3-dipolar cycloaddition of nucleobase-derived nitrones with methyl acrylate. Hydrogenolysis of the isoxazolidines containing thymine, dihydrouracil, theophylline and adenine moieties efficiently led to the formation of the [...] Read more.
Homonucleoside analogues cis-16 and trans-17 having a (5-methoxycarbonyl)isoxazolidine framework were synthesized via the 1,3-dipolar cycloaddition of nucleobase-derived nitrones with methyl acrylate. Hydrogenolysis of the isoxazolidines containing thymine, dihydrouracil, theophylline and adenine moieties efficiently led to the formation of the respective γ-lactam analogues. γ-Lactam analogues having 5-bromouracil and 5-chlorouracil fragments were synthesized by treatment of uracil-containing γ-lactams with NBS and NCS. Isoxazolidine and γ-lactam analogues of homonucleosides obtained herein were evaluated for activity against a broad range of DNA and RNA viruses. None of the compounds that were tested exhibited antiviral or cytotoxic activity at concentrations up to 100 µM. The cytostatic activities of all compounds toward nine cancerous cell lines was tested. γ-Lactams trans-15e (Cl-Ura) and cis-15h (Theo) appeared the most active toward pancreatic adenocarcinoma cells (Capan-1), showing IC50 values 21.5 and 18.2 µM, respectively. Isoxazolidine cis-15e (Cl-Ura) inhibited the proliferation of colorectal carcinoma (HCT-116). Full article
(This article belongs to the Section Medicinal Chemistry)
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14 pages, 1387 KB  
Article
A Novel Synthesis of Fused Uracils: Indenopyrimidopyridazines, Pyrimidopyridazines, and Pyrazolopyrimidines for Antimicrobial and Antitumor Evalution
by Samar El-Kalyoubi and Fatimah Agili
Molecules 2016, 21(12), 1714; https://doi.org/10.3390/molecules21121714 - 14 Dec 2016
Cited by 21 | Viewed by 5986
Abstract
A variety of different compounds of fused uracils were prepared simply by the heating of 6-hydrazinyl-1-methyl-, 6-hydrazinyl-1-propyl-, or 6-hydrazinyl-1,3-dipropyluracil under reflux with ninhydrin, isatin, benzylidene malononitrile, benzylylidene ethyl cyanoacetate, benzil, and phenacyl bromide derivatives. The newly synthesized compounds were completely screened for antimicrobial [...] Read more.
A variety of different compounds of fused uracils were prepared simply by the heating of 6-hydrazinyl-1-methyl-, 6-hydrazinyl-1-propyl-, or 6-hydrazinyl-1,3-dipropyluracil under reflux with ninhydrin, isatin, benzylidene malononitrile, benzylylidene ethyl cyanoacetate, benzil, and phenacyl bromide derivatives. The newly synthesized compounds were completely screened for antimicrobial and antitumor activity. Full article
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