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Article

Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines

by
Sergiy I. KOVALENKO
1,
Lyudmyla M. ANTYPENKO
1,*,
Andriy K. BILYI
1,
Sergiy V. KHOLODNYAK
1,
Olexandr V. KARPENKO
2,
Olexii M. ANTYPENKO
1,
Natalya S. MYKHAYLOVA
1,
Tetyana I. LOS
1 and
Olexandra S. KОLОMОЕTS
1
1
Organic and Bioorganic Chemistry Department, Zaporizhzhya State Medical University, Mayakovsky Ave. 26, 69035, Zaporizhzhya, Ukraine
2
Enamine Ltd., Oleksandra Matrosova 23, Kyiv, 01103, Ukraine
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2013, 81(2), 359-392; https://doi.org/10.3797/scipharm.1211-08
Submission received: 13 November 2012 / Accepted: 23 December 2012 / Published: 23 December 2012
Versions Notes

Abstract

The combinatorial library of novel potential anticancer agents, namely, 2-(аlkyl-, alkaryl-, aryl-, hetaryl-)[1,2,4]triazolo[1,5-c]quinazolines, was synthesized by the heterocyclization of the аlkyl-, alkaryl-, aryl-, hetarylcarboxylic acid (3Н-quinazoline-4-ylidene)hydrazides by oxidative heterocyclization of the 4-(arylidenehydrazino)quinazolines using bromine, and by the heterocyclization of N-(2-cyanophenyl)formimidic acid ethyl ester. The optimal method for synthesis of the s-triazolo[1,5-c]quinazolines appeared to be cyclocondensation of the corresponding carboxylic acid (3H-quinazoline-4-ylidene)hydrazides. The compounds’ structures were established by 1H, 13C NMR, LC- and EI-MS analysis. The in vitro screening of anticancer activity determined the most active compound to be 3,4,5-trimethoxy-N'-[quinazolin-4(3H)-ylidene]benzohydrazide (3.20) in micromolar concentrations with the GI50 level (MG_MID, GI50 is 2.29). Thus, the cancer cell lines whose growth is greatly inhibited by compound 3.20 are: non-small cell lung cancer (NCI-H522, GI50=0.34), CNS (SF-295, GI50=0.95), ovarian (OVCAR-3, GI50=0.33), prostate (PC-3, GI50=0.56), and breast cancer (MCF7, GI50=0.52), leukemia (K-562, GI50=0.41; SR, GI50=0.29), and melanoma (MDA-MB-435, GI50=0.31; SK-MEL-5, GI50=0.74; UACC-62, GI50=0.32). SAR-analysis is also discussed.
Keywords: [1,2,4]Triazolo[1,5-c]quinazolines; Anticancer activity; Carboxylic acid (3Н-quinazoline-4-ylidene)hydrazides; N-(R-Benzylidene)-N'-(3Н-quinazoline-4-ylidene)hydrazines; 2-Alkyl (alkaryl-, aryl-, hetaryl-)[1,2,4]triazolo[1,5-c]quinazolines [1,2,4]Triazolo[1,5-c]quinazolines; Anticancer activity; Carboxylic acid (3Н-quinazoline-4-ylidene)hydrazides; N-(R-Benzylidene)-N'-(3Н-quinazoline-4-ylidene)hydrazines; 2-Alkyl (alkaryl-, aryl-, hetaryl-)[1,2,4]triazolo[1,5-c]quinazolines

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MDPI and ACS Style

KOVALENKO, S.I.; ANTYPENKO, L.M.; BILYI, A.K.; KHOLODNYAK, S.V.; KARPENKO, O.V.; ANTYPENKO, O.M.; MYKHAYLOVA, N.S.; LOS, T.I.; KОLОMОЕTS, O.S. Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines. Sci. Pharm. 2013, 81, 359-392. https://doi.org/10.3797/scipharm.1211-08

AMA Style

KOVALENKO SI, ANTYPENKO LM, BILYI AK, KHOLODNYAK SV, KARPENKO OV, ANTYPENKO OM, MYKHAYLOVA NS, LOS TI, KОLОMОЕTS OS. Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines. Scientia Pharmaceutica. 2013; 81(2):359-392. https://doi.org/10.3797/scipharm.1211-08

Chicago/Turabian Style

KOVALENKO, Sergiy I., Lyudmyla M. ANTYPENKO, Andriy K. BILYI, Sergiy V. KHOLODNYAK, Olexandr V. KARPENKO, Olexii M. ANTYPENKO, Natalya S. MYKHAYLOVA, Tetyana I. LOS, and Olexandra S. KОLОMОЕTS. 2013. "Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines" Scientia Pharmaceutica 81, no. 2: 359-392. https://doi.org/10.3797/scipharm.1211-08

APA Style

KOVALENKO, S. I., ANTYPENKO, L. M., BILYI, A. K., KHOLODNYAK, S. V., KARPENKO, O. V., ANTYPENKO, O. M., MYKHAYLOVA, N. S., LOS, T. I., & KОLОMОЕTS, O. S. (2013). Synthesis and Anticancer Activity of 2-(Alkyl-, Alkaryl-, Aryl-, Hetaryl-)-[1,2,4]triazolo[1,5-c]quinazolines. Scientia Pharmaceutica, 81(2), 359-392. https://doi.org/10.3797/scipharm.1211-08

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