The synthesis and antituberculosis activity of 5′-nor carbocyclic uracil derivatives

Matyugina, Elena S.; Khandazhinskaya, Anastasia L.; Черноусова, Л. Н.; Andreevskaya, Sofya; Smirnova, Tatiana G.; Chizhov, Alexander O.; Karpenko, Inna L.; Kochetkov, S. N.; Alexandrova, L. А.

doi:10.1016/j.bmc.2012.09.019

Cited by 52 publications

(43 citation statements)

References 20 publications

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“…E 1 (k 264.2 ) = 20 300, E 2 (k 334.8 ) = 8400. 1 1-(4 0 -Hydroxy-2 0 -cyclopenten-1 0 -yl)-5-(4″butylphenylamino)uracil (13) In an analogous manner as was used to synthesize (11), compound (13) 1-(4 0 -Hydroxy-2 0 -cyclopenten-1 0 -yl)-5-(4″butyloxyphenylamino)uracil (14) In an analogous manner as was used to synthesize (11), compound (14) 1-(4 0 -Hydroxy-2 0 -cyclopenten-1 0 -yl)-5-[(4″phenoxyphenyl)amino]uracil (15) In an analogous manner as was used to synthesize (11), compound (15)…”

Section: Methodsmentioning

confidence: 99%

“…The purification described for compound (14) gave product (19) (20) The title compound was obtained as side product in the synthesis of (15). The purification described for compound (15) gave product (20) Logan, UT, USA) at 37°C in a 96-well plate in the atmosphere of 5% CO 2 . The tested compounds were dissolved in DMSO at a concentration of 40 mg/mL (stock solutions).…”

Section: -(Phenylaminomentioning

confidence: 99%

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5‐Arylaminouracil Derivatives: New Inhibitors of Mycobacterium tuberculosis

et al. 2015

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Three series of 5-arylaminouracil derivatives, including 5-(phenylamino)uracils, 1-(4'-hydroxy-2'-cyclopenten-1'-yl)-5-(phenylamino)uracils, and 1,3-di-(4'-hydroxy-2'-cyclopenten-1'-yl)-5-(phenylamino)uracils, were synthesized and screened for potential antimicrobial activity. Most of compounds had a negative effect on the growth of the Mycobacterium tuberculosis H37Rv strain, with 100% inhibition observed at concentrations between 5 and 40 μg/mL. Of those, 1-(4'-hydroxy-2'-cyclopenten-1'-yl)-3-(4‴-hydroxy-2‴-cyclopenten-1‴-yl)-5-(4″-butyloxyphenylamino)uracil proved to be the most active among tested compounds against the M. tuberculosis multidrug-resistant strain MS-115 (MIC90 5 μg/mL). In addition, the thymidylate kinase of M. tuberculosis was evaluated as a possible enzymatic target.

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Section: Methodsmentioning

confidence: 99%

Section: -(Phenylaminomentioning

confidence: 99%

5‐Arylaminouracil Derivatives: New Inhibitors of Mycobacterium tuberculosis

et al. 2015

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“…Again in the same year, a different research group published antimycobacterial results of a new series of 5′-nor carbocyclic uracil derivatives [129]. Carbocyclic nucleosides, despite the replacement of the O atom by a methylene group, are still recognized by many receptors and enzymes whose natural substrates are nucleosides, and there is evidence of their anticancer and antiviral activity [130].…”

Section: Nucleoside Analogs With Unclear Targetmentioning

confidence: 98%

Nucleoside Analogs and Tuberculosis: New Weapons Against an Old Enemy

Ferrari

Serpi

2015

Future Med. Chem.

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Purine and pyrimidine nucleoside and nucleotide analogs have been extensively studied as anticancer and antiviral agents. In addition to this, they have recently shown great potential against Mycobacterium Tuberculosis, the causative agent of TB. TB ranks as the tenth most common cause of death in the world. The current treatment for TB infection is limited by side effects and cost of the drugs and most importantly by the development of resistance to the therapy. Therefore the development of novel drugs, capable of overcoming the drawbacks of the existing treatments, has become the focus of many research programs. In parallel to that, a tremendous effort has been made to elucidate the unique metabolism of this pathogen with the aim to identify new possible targets. This review presents the state of the art in nucleoside and nucleotide analogs in the treatment of TB. In particular, we report on the inhibitory activity of this class of compounds, both in enzymatic and whole-cell assays, providing a brief insight to which reported target these novel compounds are hitting.

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“…Derivati uracila pored navedenih osnovnih uloga imaju i druge veoma značajne primene: kao baktericidi [4][5][6], u hemioterapijske svrhe [7][8][9], za usporavanje širenja akutne limfatične leukemije, normalizaciju i smanjenje broja malignih ćelija u limfoproliferativnim hroničnim oboljenjima [10][11][12], kao potencijalni lekovi u borbi protiv HIV-1 virusa [13,14]. Pored toga što imaju veliku primenu u medicini, mogu da se koriste i za dobijanje PVC materijala koji se koriste kao toplotni stabilizatori [15].…”

Section: Uvodunclassified