932-53-6Relevant articles and documents
Synthesis and evaluation of 6-Aza-2′-deoxyuridine monophosphate analogs as inhibitors of thymidylate synthases, and as substrates or inhibitors of thymidine monophosphate kinase in mycobacterium tuberculosis
Koegler, Martin,Busson, Roger,De Jonghe, Steven,Rozenski, Jef,Van Belle, Kristien,Louat, Thierry,Munier-Lehmann, Helne,Herdewijn, Piet
experimental part, p. 536 - 556 (2012/05/20)
A series of 5-substituted analogs of 6-aza-2′-deoxyuridine 5′-monophosphate, 6-aza-dUMP, has been synthesized and evaluated as potential inhibitors of the two mycobacterial thymidylate synthases (i.e., a flavin-dependent thymidylate synthase, ThyX, and a classical thymidylate synthase, ThyA). Replacement of C(6) of the natural substrate dUMP by a N-atom in 6-aza-dUMP 1a led to a derivative with weak ThyX inhibitory activity (33% inhibition at 50 μM). Introduction of alkyl and aryl groups at C(5) of 1a resulted in complete loss of inhibitory activity, whereas the attachment of a 3-(octanamido)prop-1-ynyl side chain in derivative 3 retained the weak level of mycobacterial ThyX inhibition (40% inhibition at 50 μM). None of the synthesized derivatives displayed any significant inhibitory activity against mycobacterial ThyA. The compounds have also been evaluated as potential inhibitors of mycobacterial thymidine monophosphate kinase (TMPKmt). None of the derivatives showed any significant TMPKmt inhibition. However, replacement of C(6) of the natural substrate (dTMP) by a N-atom furnished 6-aza-dTMP (1b), which still was recognized as a substrate by TMPKmt. Copyright
Synthesis and antimicrobial evaluation of 6-azauracil non-nucleosides
El-Brollosy, Nasser R.
scheme or table, p. 1483 - 1490 (2009/12/26)
The present study describes synthesis and antimicrobial evaluation of a series of novel 6-azauracil non-nucleosides. Reaction of silylated 6-azauracils with the appropriate chloroethers gave the corresponding non-nucleosides. 1-(Allyloxymethy)-6-azauracils and non-nucleosides bearing indanyl, cyclohexenyl, and cyclohexyl moieties were obtained via silylation of 6-azauracils followed by treatment with the appropriate acetals. Selected compounds were tested for their in vitro antimicrobial activity against a panel of standard strains of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Four compounds showed marked inhibitory activity particularly against the tested Gram-positive bacteria.
Comparative studies for selective deprotection of the N-arylideneamino moiety from heterocyclic amides: kinetic and theoretical studies. Part 2
Al-Awadi, Nouria A.,Ibrahim, Yehia A.,Dib, Hicham H.,Ibrahim, Maher R.,George, Boby J.,Abdallah, Mariam R.
, p. 6214 - 6221 (2007/10/03)
4-Benzylideneamino-1,2,4-triazine-3,5(2H,4H)-diones (2-5), 6-styryl-1,2,4-triazine-3,5(2H,4H)-dione (6), and 6-styryl-2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one (7) were synthesized and pyrolyzed in the gas phase. The kinetic effect of changing the substituent on the triazine ring from hydrogen to methyl, phenyl, and styryl was measured. Analyses of the pyrolyzates of 2-5 showed the elimination products to be benzonitrile and the triazine fragment, while the pyrolyzates of 6 and 7 reveal the formation of cis- and trans-cinnamonitriles. Theoretical study of the pyrolysis reactions of 2-5 using an ab initio SCF method was investigated.
