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Synthesis, reactions, and biological activity of some triazine derivatives containing sulfa drug moieties

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Abstract

Thienyl-triazine-sulphonamide conjugates were prepared from their precursor amines using triethyl orthoformate or ethyl chloroformate as cross coupling reagents. The progress of these reactions was investigated by spectral (IR, NMR, MS) and microanalytical techniques. The synthesized compounds were in vitro screened for antibacterial, antifungal, antioxidant, and anticancer activity. 4-[({[3-Mercapto-5-oxo-6-[2-(2-thienyl)vinyl]-1,2,4-triazin-4(5H)-yl]imino}methyl)amino]-benzenesulfonamide turned out to be a powerful antibacterial agent, while all the compounds prepared were inactive against fungal species tested. 4-{[({8-Cyano-4-oxo-3-[2-(2-thienyl)vinyl]-4H,8H-[1,2,4]triazino[3,4-b][1,3,4]thiadiazin7-yl}amino)(ethoxy)methyl]amino}benzenesulfonamide displayed in vitro promising cytotoxicity against Ehrlich ascites carcinoma cell line with concurrent attenuation of malonodinitrile and it was unique among other compounds being unable to increase glutathione S-transferase and reduced glutathione S-transferase activities. This compound exhibited also good antioxidant properties that together with its cytotoxicity nominated it for further investigation in cancer research.

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Abbreviations

BACE1:

Beta-secretase 1

DPPH:

2,2-diphenyl-1-picrylhydrazyl

EACC:

Ehrlich ascites carcinoma cell line

GST:

glutathione S-transferase

GST-Rd:

reduced glutathione S-transferase

HIV:

human immunodeficiency virus

MDR:

multidrug resistance

P-gp:

P-glycoproteins

SAR:

structure-activity relationship

VEGFR:

vascular endothelial growth factor receptor

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Taif University, Taif, 21974, Kingdom of Saudi Arabia

    M. R. E. Aly, A. A. Gobouri, S. H. Abdel Hafez & H. A. Saad

  2. Department of Chemistry, Faculty of Applied Science, Port Said University, Port Said, Egypt

    M. R. E. Aly

  3. Department of Chemistry, Faculty of Science, Assiut University, Assiut, Egypt

    S. H. Abdel Hafez

  4. Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt

    H. A. Saad

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  1. M. R. E. Aly
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  2. A. A. Gobouri
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  3. S. H. Abdel Hafez
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  4. H. A. Saad
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Correspondence to H. A. Saad.

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Aly, M.R.E., Gobouri, A.A., Abdel Hafez, S.H. et al. Synthesis, reactions, and biological activity of some triazine derivatives containing sulfa drug moieties. Russ J Bioorg Chem 41, 437–450 (2015). https://doi.org/10.1134/S1068162015040032

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