4878-46-0Relevant academic research and scientific papers
5-arylaminouracil derivatives: New inhibitors of Mycobacterium tuberculosis
Matyugina, Elena,Novikov, Mikhail,Babkov, Denis,Ozerov, Alexander,Chernousova, Larisa,Andreevskaya, Sofia,Smirnova, Tatiana,Karpenko, Inna,Chizhov, Alexander,Murthu, Pravin,Lutz, Stefan,Kochetkov, Sergei,Seley-Radtke, Katherine L.,Khandazhinskaya, Anastasia L.
, p. 1387 - 1396 (2016/02/05)
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. Three series of 5-arylaminouracil derivatives were synthesized and screened for potential antimicrobial activity. Most of compounds had a negative effect on the growth of the M. 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).
Synthesis of 1-(aryloxyalkyl)-5-(arylamino)uracils
Ozerov,Novikov,Brel',Solodunova
, p. 611 - 616 (2007/10/03)
In an attempt to obtain new non-nucleoside inhibitors of the reverse transcriptase HIV-1, we have carried out the synthesis of 1-(benzyloxymethyl)- and 1-[2-(4-R-phenoxy)ethyl]-5-(arylamino)uracils. Indirect alkylation of trimethylsilyl derivatives of 5-(arylamino)uracils with benzyl chloromethyl ether by the Gilbert-Jones method did not affect the exocyclic amino group and gave the corresponding 1-(benzyloxymethyl) derivatives in 58-74% yield. Alkylation of 5-(arylamino)uracils with 1-bromo-2-(4-R-phenoxy)ethane in anhydrous DMF in the presence of potassium carbonate gave a mixture of N1-mono- and N1,N1-disubstituted products with an overall yield of 46-55%. 1998 Plenum Publishing Corporation.
