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Scientia Pharmaceutica is published by MDPI from Volume 84 Issue 3 (2015). Articles in this Volume were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence. Articles are hosted by MDPI on mdpi.com as a courtesy and upon agreement with Austrian Pharmaceutical Society (Österreichische Pharmazeutische Gesellschaft, ÖPhG).
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Sci. Pharm. 2012, 80(1), 37-66; doi:10.3797/scipharm.1111-15 (registering DOI)

Synthesis of New 6-{[ω-(Dialkylamino(heterocyclyl)alkyl]thio}- 3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones and Evaluation of their Anticancer and Antimicrobial Activities

1
Department of Pharmacy, Zaporozhye State Medical University, Mayakovsky ave., 26, 69035, Zaporozhye, Ukraine
2
Department of Pharmacy, Crimean State Medical University, av. Lenina, 5/7, 95006, Simferopol, Ukraine
*
Author to whom correspondence should be addressed.
Received: 20 November 2011 / Accepted: 23 December 2011 / Published: 23 December 2011
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Abstract

Several novel 6-thio-3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-based com-pounds containing an ω-(dialkylamino(heterocyclyl)]alkyl fragment were synthe-sized to examine their anticancer activity. Some of the 6-{[ω-(hetero-cyclyl)alkyl]thio}-3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones (3.1–3.10) were obtained by the nucleophilic substitution of 6-[ω-halogenalkyl]thio-3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones (2.1–2.8) with azaheterocycles. Alter-natively, compounds 3.1–3.22 were synthesized by alkylation of 3-R-6-thio-2Н-[1,2,4]triazino[2,3-c]quinazoline-2-ones potassium salts (1.1–1.4) with (2-chloro-ethyl)-N,N-dialkylamine hydrochlorides or 1-(2-chloroethyl)heterocycle hydro-chlorides. The structures of compounds were elucidated by 1H, 13C NMR, LC–MS and EI-MS analysis. Then anticancer and antibacterial, biolumi-nescence inhibition of Photobacterium leiognathi Sh1 activities of the sub-stances were tested in vitro. It was found that compound 3.18 possessed a wide range of anticancer activity against 27 cell lines of cancer: non-small cell lung, сolon, CNS, ovarian, renal, prostate, breast, melanoma and leukemia (log GI50 < −5.65). The “structure-activity” relationship was discussed. COMPARE analysis for synthesized anticancer active compounds was performed.
Keywords: 2H-[1,2,4]Triazino[2,3-c]quinazolin-2-one; Bioluminescence inhibition; Chemotherapeutic; Antibacterial; Anticancer; Cytostatic; COMPARE; SAR 2H-[1,2,4]Triazino[2,3-c]quinazolin-2-one; Bioluminescence inhibition; Chemotherapeutic; Antibacterial; Anticancer; Cytostatic; COMPARE; SAR
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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BEREST, G.G.; VOSKOBOYNIK, O.Y.; KOVALENKO, S.I.; NOSULENKO, I.S.; ANTYPENKO, L.M.; ANTYPENKO, O.M.; SHVETS, V.M.; KATSEV, A.M. Synthesis of New 6-{[ω-(Dialkylamino(heterocyclyl)alkyl]thio}- 3-R-2H-[1,2,4]triazino[2,3-c]quinazoline-2-ones and Evaluation of their Anticancer and Antimicrobial Activities. Sci. Pharm. 2012, 80, 37-66.

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