Next Article in Journal
Cytotoxic and Antifungal Activities of Diverse α-Naphthylamine Derivatives
Previous Article in Journal
Synthesis of New N,N'-Bis(5-arylidene-4-oxo-4,5-dihydrothiazolin-2-yl)piperazine Derivatives Under Microwave Irradiation and Preliminary Biological Evaluation
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Sci. Pharm.
Volume 80
Issue 4
10.3797/scipharm.1208-07
scipharm-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
Scientia Pharmaceutica is published by MDPI from Volume 84 Issue 3 (2016). Previous articles were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence, and they are hosted by MDPI on mdpi.com as a courtesy and upon agreement with Austrian Pharmaceutical Society (Österreichische Pharmazeutische Gesellschaft, ÖPhG).
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
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

Share and Cite

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

Article Metrics

Back to TopTop