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. 2014 Apr 22;19(4):5163-90.
doi: 10.3390/molecules19045163.

Antioxidant and antitumor activities of new synthesized aromatic C-nucleoside derivatives

Mohamed M El Sadek  1 , Nagwa S Abd El-Dayem  2 , Seham Y Hassan  3 , Mohamed A Mostafa  4 , Galila A Yacout  5
Affiliations

Antioxidant and antitumor activities of new synthesized aromatic C-nucleoside derivatives

Mohamed M El Sadek et al. Molecules. .

Abstract

The carbohydrazide 1 was used as the precursor for the synthesis of a number of new aromatic C-nucleosides containing 1,3,4-oxadiazole 7, [1,3,4]oxadiazolo[2,3-a]isoindole 10b and pyrazole units 18. On the other hand, the thiosemicarbazone 20 was used as the key intermediate for synthesis of 1,3,4-oxadiazole and 1,2,4-triazole-3-thione derivatives 21 and 23. The antioxidant activities of the prepared compounds were evaluated. The carbohydrazide 1 in particular was found to have potent antioxidant and antitumor activity.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of carbohydrazones 3a–e and 4.
Scheme 2
Scheme 2
Synthesis of aromatic C-nucleosides 5–9.
Scheme 3
Scheme 3
Synthesis of [1,3,4]oxadiazolo[2,3-a]-isoindole 10b.
Scheme 4
Scheme 4
Proposed mechanism for formation of [1,3,4]oxadiazolo[2,3-a]isoindole 10b.
Scheme 5
Scheme 5
Synthesis of aromatic C-nucleosides 12–17.
Scheme 6
Scheme 6
Synthesis of pyrazole derivatives 18 and 19.
Scheme 7
Scheme 7
Synthesis of 1,3,4-oxadiazoles 21 and 22.
Scheme 8
Scheme 8
Synthesis of 4-phenyl-2H-1,2,4-triazole-3(4H)-thiones 23–26.
Figure 1
Figure 1
Free radical scavenging activity of vitamin E.
Figure 2
Figure 2
Free radical scavenging activity of compounds 1, 3c–e.
Figure 3
Figure 3
Free radical scavenging activity of compounds 4–6, 13.
Figure 4
Figure 4
Free radical scavenging activity of compounds 16–19.
Figure 5
Figure 5
Free radical scavenging activity of compounds 20–22.
Figure 6
Figure 6
Free radical scavenging activity of compounds 23–26.
Figure 7
Figure 7
Viability activity against HepG-2 of compound 1.
Figure 8
Figure 8
Viability activity against HCT-116 of compound 1.
Figure 9
Figure 9
Viability activity against MCF-7 of compound 1.
See this image and copyright information in PMC

References

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