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Volume 80
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Article

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

by
Galina G. BEREST
1,
Olexiy Y. VOSKOBOYNIK
1,
Sergiy I. KOVALENKO
1,*,
Inna S. NOSULENKO
1,
Lyudmyla M. ANTYPENKO
1,
Olexii M. ANTYPENKO
1,
Volodymyr M. SHVETS
1 and
Andriy M. KATSEV
2
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.
Sci. Pharm. 2012, 80(1), 37-66; https://doi.org/10.3797/scipharm.1111-15
Submission received: 20 November 2011 / Accepted: 23 December 2011 / Published: 23 December 2011
Versions Notes

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

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MDPI and ACS Style

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. https://doi.org/10.3797/scipharm.1111-15

AMA Style

BEREST GG, VOSKOBOYNIK OY, KOVALENKO SI, NOSULENKO IS, ANTYPENKO LM, ANTYPENKO OM, SHVETS VM, KATSEV AM. 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. Scientia Pharmaceutica. 2012; 80(1):37-66. https://doi.org/10.3797/scipharm.1111-15

Chicago/Turabian Style

BEREST, Galina G., Olexiy Y. VOSKOBOYNIK, Sergiy I. KOVALENKO, Inna S. NOSULENKO, Lyudmyla M. ANTYPENKO, Olexii M. ANTYPENKO, Volodymyr M. SHVETS, and Andriy M. KATSEV. 2012. "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" Scientia Pharmaceutica 80, no. 1: 37-66. https://doi.org/10.3797/scipharm.1111-15

APA Style

BEREST, G. G., VOSKOBOYNIK, O. Y., KOVALENKO, S. I., NOSULENKO, I. S., ANTYPENKO, L. M., ANTYPENKO, O. M., SHVETS, V. M., & KATSEV, A. M. (2012). 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. Scientia Pharmaceutica, 80(1), 37-66. https://doi.org/10.3797/scipharm.1111-15

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