Heterocycles with a pyrido[3,2-e]-1,3-selenazine and pyrido[3,4-e]-1,3-selenazine ring systems

Kristián, Pavol; Koščík, Dušan; Gonda, Jozef

doi:10.1135/cccc19833567

Cited by 15 publications

(3 citation statements)

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“…The general structure of the designed compounds is depicted in Figure 2, with carbo-and hetero-cyclic moieties (in blue) and variability on aniline substitution (in green). The proposed synthesis of these compounds was similar to the protocols reported previously for analogous compounds [43,[53][54][55]. Keeping all this previous experience in mind, in this work, we planned the design of a new library of forty seven acylselenoureas with both a potential anticancer and antioxidant activity following a fragment-based approach for drug design [48], varying the two sides of the molecule, searching for a synergistic effect between the fragments and the acylselenourea itself.…”

Section: Introductionmentioning

confidence: 95%

“…The general structure of the designed compounds is depicted in Figure 2, with carbo-and hetero-cyclic moieties (in blue) and variability on aniline substitution (in green). The proposed synthesis of these compounds was similar to the protocols reported previously for analogous compounds [43,[53][54][55]. The dose-and time-dependent radical scavenging activity of all of the synthesized compounds were assessed in vitro using the colorimetric assays of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS).…”

Section: Introductionmentioning

confidence: 99%

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Novel N,N′-Disubstituted Acylselenoureas as Potential Antioxidant and Cytotoxic Agents

et al. 2020

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Selenium compounds are pivotal in medicinal chemistry for their antitumoral and antioxidant properties. Forty seven acylselenoureas have been designed and synthesized following a fragment-based approach. Different scaffolds, including carbo- and hetero-cycles, along with mono- and bi-cyclic moieties, have been linked to the selenium containing skeleton. The dose- and time-dependent radical scavenging activity for all of the compounds were assessed using the in vitro 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) assays. Some of them showed a greater radical scavenging capacity at low doses and shorter times than ascorbic acid. Therefore, four compounds were evaluated to test their protective effects against H2O2-induced oxidative stress. One derivative protected cells against H2O2-induced damage, increasing cell survival by up to 3.6-fold. Additionally, in vitro cytotoxic activity of all compounds was screened against several cancer cells. Eight compounds were selected to determine their half maximal inhibitory concentration (IC50) values towards breast and lung cancer cells, along with their selectivity indexes. The breast cancer cells turned out to be much more sensitive than the lung. Two compounds (5d and 10a) stood out with IC50 values between 4.2 μM and 8.0 μM towards MCF-7 and T47D cells, with selectivity indexes greater than 22.9. In addition, compound 10b exhibited dual antioxidant and cytotoxic activities. Although further evidence is needed, the acylselenourea scaffold could be a feasible frame to develop new dual agents.

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Section: Introductionmentioning

confidence: 95%

“…The general structure of the designed compounds is depicted in Figure 2, with carbo-and hetero-cyclic moieties (in blue) and variability on aniline substitution (in green). The proposed synthesis of these compounds was similar to the protocols reported previously for analogous compounds [43,[53][54][55]. The dose-and time-dependent radical scavenging activity of all of the synthesized compounds were assessed in vitro using the colorimetric assays of 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS).…”

Section: Introductionmentioning

confidence: 99%

Novel N,N′-Disubstituted Acylselenoureas as Potential Antioxidant and Cytotoxic Agents

et al. 2020

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“…The reaction of allenyl isoselenocyanate with seleno-containing nucleophiles gave selenazoles 56 (Scheme 31) [27]. The reaction of 20 and 21 with sodium hydroselenide afforded the respective 2-selenoxo-4-oxopyrido-1,3-selenazines 57 and 58 (Scheme 32) [35]. 1,3-Selenazines and 1,3-selenzoles have been prepared from isoselenocyanates via diselenocarbamate intermediates [56].…”

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confidence: 99%

Isoselenocyanates: A Powerful Tool for the Synthesis of Selenium-Containing Heterocycles

2007

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Selenium-containing heterocyclic compounds have been well recognized, not only because of their remarkable reactivities and chemical properties, but also because of their diverse pharmaceutical applications. In this context, isoselenocyanates have been emerged as a powerful tool for the synthesis of selenium-containing heterocycles, since they are easy to prepare and store and are safe to handle. In this review the recent advances in the development of synthesis methods for selenium-containing heterocycles from isoselenocyanates are presented and discussed.

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Selenium and tellurium heterocycles

Renson

1986

PATAI'S Chemistry of Functional Groups

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Heterocycles with a pyrido[3,2-e]-1,3-selenazine and pyrido[3,4-e]-1,3-selenazine ring systems

Cited by 15 publications

References 0 publications

Novel N,N′-Disubstituted Acylselenoureas as Potential Antioxidant and Cytotoxic Agents

Novel N,N′-Disubstituted Acylselenoureas as Potential Antioxidant and Cytotoxic Agents

Isoselenocyanates: A Powerful Tool for the Synthesis of Selenium-Containing Heterocycles

Selenium and tellurium heterocycles

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