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Volume 80
Issue 4
10.3797/scipharm.1208-07
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Article

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

by
Sergey I. KOVALENKO
1,*,
Inna S. NOSULENKO
1,
Alexey Yu. VOSKOBOYNIK
1,
Galina G. BEREST
1,
Lyudmyla N. ANTYPENKO
1,
Alexey N. ANTYPENKO
1 and
Andrey M. KATSEV
2
1
Zaporozhye State Medical University, 69035, Zaporozhye, Ukraine
2
Crimean State Medical University, 95006, Simferopol, Ukraine
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2012, 80(4), 837-866; https://doi.org/10.3797/scipharm.1208-07
Submission received: 14 August 2012 / Accepted: 4 October 2012 / Published: 4 October 2012
Versions Notes

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

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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. https://doi.org/10.3797/scipharm.1208-07

AMA Style

KOVALENKO SI, NOSULENKO IS, VOSKOBOYNIK AY, BEREST GG, ANTYPENKO LN, ANTYPENKO AN, KATSEV AM. 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. Scientia Pharmaceutica. 2012; 80(4):837-866. https://doi.org/10.3797/scipharm.1208-07

Chicago/Turabian Style

KOVALENKO, Sergey I., Inna S. NOSULENKO, Alexey Yu. VOSKOBOYNIK, Galina G. BEREST, Lyudmyla N. ANTYPENKO, Alexey N. ANTYPENKO, and Andrey M. KATSEV. 2012. "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" Scientia Pharmaceutica 80, no. 4: 837-866. https://doi.org/10.3797/scipharm.1208-07

APA Style

KOVALENKO, S. I., NOSULENKO, I. S., VOSKOBOYNIK, A. Y., BEREST, G. G., ANTYPENKO, L. N., ANTYPENKO, A. N., & KATSEV, A. M. (2012). 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. Scientia Pharmaceutica, 80(4), 837-866. https://doi.org/10.3797/scipharm.1208-07

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