Synthesis and Biological Evaluation of 1,2,5-OxadiazoleN-Oxide Derivatives as Potential Hypoxic Cytotoxins and DNA-Binders

Cerecetto, Hugo; González, Mercedes; Risso, Mariela; Seoane, Gustavo; Ceráin, Adela López de; Ezpeleta, Olga; Monge, Antonio; Suescun, Leopoldo; Mombrú, Álvaro W.; Bruno, Ana M.

doi:10.1002/1521-4184(200011)333:11<387::aid-ardp387>3.0.co;2-n

Cited by 18 publications

(2 citation statements)

References 34 publications

(37 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N 4 -n-butylsemicarbazide, N 4 -(2-naphthyl)semicarbazide, 2-hydroxynaphtalen-1-carboxaldehyde and V IV O(acac) 2 (where acac = acetylacetonate), were prepared according to well established literature procedures [28][29][30][31].…”

Section: Methodsmentioning

confidence: 99%

Vanadium(V) complexes with salicylaldehyde semicarbazone derivatives bearing in vitro anti-tumor activity toward kidney tumor cells (TK-10): crystal structure of [VVO2(5-bromosalicylaldehyde semicarbazone)]

Noblía

Vieites

Parajón‐Costa

et al. 2005

Journal of Inorganic Biochemistry

Self Cite

121

View full text Add to dashboard Cite

Section: Methodsmentioning

confidence: 99%

Vanadium(V) complexes with salicylaldehyde semicarbazone derivatives bearing in vitro anti-tumor activity toward kidney tumor cells (TK-10): crystal structure of [VVO2(5-bromosalicylaldehyde semicarbazone)]

Noblía

Vieites

Parajón‐Costa

et al. 2005

Journal of Inorganic Biochemistry

Self Cite

121

View full text Add to dashboard Cite

“…1 In the course of our synthetic chemical approach we developed 1,2,5-oxadiazole N-oxide derivatives as potential herbicides, 2 bioreductive compounds, [3][4][5][6] and antitrypanosomal drugs, 7,8 using previously described synthetic methods. 9 During the structural elucidation of these derivatives, we were interested in knowing about the presence and the exact location of the N-oxide functionality.…”

Section: Introductionmentioning

confidence: 99%

Mass spectrometry of 1,2,5-oxadiazole N-oxide derivatives: use of deuterated analogues in fragmentation pattern studies

Cerecetto¹,

González²,

Seoane³

et al. 2004

J. Braz. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

Reportamos neste trabalho o estudo sistemático de fragmentação dos derivados de N-óxidos de 1,2,5-oxadiazóis por espectroscopia de massa, usando análogos marcados com deutério para identificar algumas fragmentações críticas. Foi confirmada a perda neutra de CH 2 O a partir do N 2 -óxido de 3-hidroximetil-4-fenil-1,2,5-oxidiazol, usando o análogo mono-deuterado. A perda de OH, a partir do oxigênio do N-óxido, por um rearranjo β-H e δ-H, foi claramente verificada a partir do N 2 -óxido de 3-(4-metilpiperazina-1-metil)-4-fenil-1,2,5-oxidiazol, usando-se o analogo tetra-deuterado adequado. O isômero N-óxido e análogos desoxigenados foram também usados para confirmar a participação do fragmento óxido no processo de defragmentação. This paper reported on the study of fragmentation pattern in mass spectrometry of 1,2,5-oxadiazole N-oxide derivatives involving deuterium-labeled analogues to identify some critical fragmentations. A neutral CH 2 O loss from 3-hydroxymethyl-N 2 -oxide-4-phenyl-1,2,5-oxadiazole was confirmed with the corresponding mono-deuterated analogue. An OH loss, involving the oxygen of N-oxide, via β-H and δ-H rearrangement, was clearly revealed from 3-(4-methylpiperazine-1-ylmethyl)-N 2 -oxide-4-phenyl-1,2,5-oxadiazole using the adequate tetra-deuterated analogue. N-oxide isomer and deoxygenated analogues were also used to confirm the participation of the oxide moiety in the fragmentation process.

show abstract

1, 2, 4‐Triazine N‐oxide Derivatives: Studies as Potential Hypoxic Cytotoxins. Part II.

Cerecetto

González

Onetto

et al. 2004

Archiv der Pharmazie

View full text Add to dashboard Cite

New 1, 2, 4-Triazine N-oxide and N, N'-dioxide derivatives were synthesized in order to obtain compounds as selective hypoxic cell cytotoxins. The starting heterocycles have been prepared using a standard microwave oven in a clean and good-yielded process. The reactivity of methyl-1, 2, 4-triazine N(4)-oxide and N(1), N(4)-dioxide with different electrophilic agents has been studied. The desired products were obtained only when iminium electrophiles were employed. The regioselectivity of this process has been studied by means of experimental and theoretical (at ab initio level) procedures. Theoretically was expected that the most stable intermediates where the benzylic-like anion from position 5. A fact which agreed with the experimental observed regioselectivity. The new compounds were tested for their cytotoxicity in oxia and hypoxia. Some of them proved to be less active in hypoxic conditions than tirapazamine, 3-amino-benzo[1, 2-e]1, 2, 4-triazine N(1), N(4)-dioxide. Derivative 19, 6-methyl-5-[2-(5-nitrothienyl)ethenyl)-1, 2, 4-triazine N(4)-oxide, was the most cytotoxic compound, but it was non-selective.

show abstract

Synthesis and Biological Evaluation of 1,2,5-OxadiazoleN-Oxide Derivatives as Potential Hypoxic Cytotoxins and DNA-Binders

Cited by 18 publications

References 34 publications

Vanadium(V) complexes with salicylaldehyde semicarbazone derivatives bearing in vitro anti-tumor activity toward kidney tumor cells (TK-10): crystal structure of [VVO2(5-bromosalicylaldehyde semicarbazone)]

Vanadium(V) complexes with salicylaldehyde semicarbazone derivatives bearing in vitro anti-tumor activity toward kidney tumor cells (TK-10): crystal structure of [VVO2(5-bromosalicylaldehyde semicarbazone)]

Mass spectrometry of 1,2,5-oxadiazole N-oxide derivatives: use of deuterated analogues in fragmentation pattern studies

1, 2, 4‐Triazine N‐oxide Derivatives: Studies as Potential Hypoxic Cytotoxins. Part II.

Contact Info

Product

Resources

About