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Sci. Pharm. 2012, 80(4), 837-866; doi:10.3797/scipharm.1208-07

Substituted 2-[(2-Oxo-2H-[1,2,4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with Thiazole and Thiadiazole Fragments: Synthesis, Physicochemical Properties, Cytotoxicity, and Anticancer Activity

1
Zaporozhye State Medical University, 69035, Zaporozhye, Ukraine
2
Crimean State Medical University, 95006, Simferopol, Ukraine
*
Author to whom correspondence should be addressed.
Received: 14 August 2012 / Accepted: 4 October 2012 / Published: 4 October 2012
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Abstract

The series of novel N-R-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamides with thiazole and thiadiazole fragments in a molecule were obtained by alkylation of potassium salts 1.1–1.4 by N-hetaryl-2-chloro-acetamides and by aminolysis of activated acids 2.1–2.4 with N,N'-carbonyl-diimidazole (CDI). The structures of compounds were determined by IR, 1H NMR, MS, and EI-MS analysis. The results of cytotoxicity evaluated by the bio-luminescence inhibition of bacterium Photobacterium leiognathi, Sh1 showed that the compounds have considerable cytotoxicity. The synthesized compounds were tested for anticancer activity in NCI against 60 cell lines. Among the highly active compounds 3.1, 3.2, and 6.5, 2-[(3-methyl-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]-N-(1,3-thiazol-2-yl)acetamide (3.1) was found to be the most active anticancer agent against the cell lines of colon cancer (GI50 at 0.41–0.69 μМ), melanoma (GI50 0.48–13.50 μM), and ovarian cancer (GI50 0.25–5.01 μM). The structure-activity relationship (SAR-analysis) was discussed.
Keywords: [1,2,4]Triazino[2,3-c]quinazolines; Thiazoles; Thiadiazoles; Anticancer; SAR; Bioluminescence inhibition [1,2,4]Triazino[2,3-c]quinazolines; Thiazoles; Thiadiazoles; Anticancer; SAR; Bioluminescence inhibition
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

KOVALENKO, S.I.; NOSULENKO, I.S.; VOSKOBOYNIK, A.Y.; BEREST, G.G.; ANTYPENKO, L.N.; ANTYPENKO, A.N.; KATSEV, A.M. Substituted 2-[(2-Oxo-2H-[1,2,4]triazino [2,3-c]quinazolin-6-yl)thio]acetamides with Thiazole and Thiadiazole Fragments: Synthesis, Physicochemical Properties, Cytotoxicity, and Anticancer Activity. Sci. Pharm. 2012, 80, 837-866.

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