2010
DOI: 10.1111/j.1751-1097.2010.00832.x
|View full text |Cite
|
Sign up to set email alerts
|

Abstract: Novel 7-substituted 6-oxo-6,9-dihydro[1,2,5]selenadiazolo[3,4-h]quinoline (SeQ(1-6)) and 8-substituted 9-oxo-6,9-dihydro[1,2,5]selenadiazolo[3,4-f ]quinoline derivatives (SeQN(1-5)) with R(7), R(8) =H, COOC(2) H(5), COOCH(3), COOH, COCH(3) or CN were synthesized and their spectral characteristics were obtained by UV/Vis spectroscopy. Ultraviolet A photoexcitation of the selenadiazoloquinolones in dimethylsulfoxide or acetonitrile resulted in the formation of paramagnetic species coupled with molecular oxygen a… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
4
1

Citation Types

1
57
0

Year Published

2011
2011
2023
2023

Publication Types

Select...
8

Relationship

6
2

Authors

Journals

citations
Cited by 35 publications
(58 citation statements)
references
References 68 publications
1
57
0
Order By: Relevance
“…[25][26][27][28] Detailed investigation of their photoinduced processes confirmed that these compounds can behave as photosensitizers, generating ROS in the presence of molecular oxygen upon UVA irradiation. [26] The generation of paramagnetic intermediates and singlet oxygen upon photoexcitation of the selenadiazoloquinolones studied was monitored by electron paramagnetic resonance (EPR) spectroscopy. UVA photoexcitation of the selenadiazoloquinolones in aprotic solvents resulted in the activation of molecular oxygen generating the superoxide radical anion and singlet oxygen.…”
Section: Introductionmentioning
confidence: 95%
See 1 more Smart Citation
“…[25][26][27][28] Detailed investigation of their photoinduced processes confirmed that these compounds can behave as photosensitizers, generating ROS in the presence of molecular oxygen upon UVA irradiation. [26] The generation of paramagnetic intermediates and singlet oxygen upon photoexcitation of the selenadiazoloquinolones studied was monitored by electron paramagnetic resonance (EPR) spectroscopy. UVA photoexcitation of the selenadiazoloquinolones in aprotic solvents resulted in the activation of molecular oxygen generating the superoxide radical anion and singlet oxygen.…”
Section: Introductionmentioning
confidence: 95%
“…UVA photoexcitation of the selenadiazoloquinolones in aprotic solvents resulted in the activation of molecular oxygen generating the superoxide radical anion and singlet oxygen. [26] Despite the supposed anticancer mechanisms of selenium-containing compounds, an excess of intracellular ROS may attack the cellular membrane lipids, proteins and DNA, inhibiting their normal functions by oxidative damage. Consequently, the derivatives showing the highest photoactivity were chosen for biological experiments with murine and human neoplastic cell lines.…”
Section: Introductionmentioning
confidence: 99%
“…5,6 In our previous research, 7-substituted selenadiazolo [3,4-h]quinolones and 8-substituted selenadiazolo [3,4-f]quinolones (R 7 , R 8 = H, CN, COCH 3 , COOMe, COOEt, COOH) were successfully synthetized by the GouldJacobs reaction 7,8 and their biological/photobiological activity was investigated together with their EPR spectroscopy. [9][10][11][12] Antimicrobial activity of 7-substituted selenadiazolo [3,4-Analogously, treatment of selenadiazoloquinolone 4 with EtI in the presence of K 2 CO 3 afforded a mixture of N-and O-ethylated products 5 and 6 in almost the same ratio as in the previous case. Despite the fact that formation of selanadiazoloquinoline 6 was not observed when NaH was applied as the base, desired 6-ethylselenadiazoloquinolone 5 was isolated only in 26% yield (Scheme 2).…”
Section: Introductionmentioning
confidence: 57%
“…The angular annulation of the selenadiazole and pyridone ring was confirmed by the coupling constants 3 J HH (about 9.5 Hz)…”
Section: Methodsmentioning
confidence: 89%
“…Herein, we report the application of the Gould-Jacobs reaction to 5-amino-2,1,3-benzoselenadiazole yielding only angularly annulated 8-substituted [1,2,5]selenadiazolo [3,4-f]quinolones 1. The presence of selenium as a photosensitive element in the structure of 4-quinolones could lead to potential biological/photobiological activity 3,4 as well as to interesting photochemical and spectral characteristics. 5,6 On the other hand, it is commonly thought that organic compounds containing selenium are very poisonous and foul but toxicity of weakly volatile selenaheterocycles should be low and they are odourless.…”
Section: Introductionmentioning
confidence: 99%