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Molecules 2003, 8(11), 756-769;

Synthesis and Biological Evaluation of Quinazoline-4-thiones

Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1205, 500 05 Hradec Králové, Czech Republic
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, 842 15 Bratislava, Slovak Republic
Department of Pharmacy, Division of Pharmacognosy, University of Helsinki, P.O. Box 56, (Viikinkaari 5), Helsinki, Finland
National Reference Laboratory for Mycobacterium Kansasii, Institute of Hygiene, 728 92 Ostrava, Czech Republic
Author to whom correspondence should be addressed.
Received: 25 August 2003 / Revised: 30 September 2003 / Accepted: 30 September 2003 / Published: 15 November 2003
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Several 2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thiones and 2-methyl-3-phenylquinazoline-4(3H)-thiones were synthesized and tested for their antimycobacterial, photosynthesis-inhibiting, and antialgal activity. Antimycobacterially active compounds were found among the 6-chloro substituted compounds. 6-Chloro-3-(4-isopropylphenyl)-2-methylquinazoline-4(3H)-thione exhibited higher activity than the isoniazid standard against Mycobacterium avium and M. kansasii. Most of the compounds possessed photosynthesis-inhibiting activity. 6-Chloro-2,2-dimethyl-3-phenyl-1,2-dihydroquinazoline-4(3H)-thione and its 3´-chloro- and 3´,4´-dichloro analogs were most effective in the inhibition of oxygen evolution rate in spinach chloroplasts. Of compounds selected for toxicological screening, 6-chloro-3-(4-isopropylphenyl)-2-methyl-quinazoline-4(3H)-thione was the only one active in the brine shrimp bioassay. View Full-Text
Keywords: Quinazoline-4-thiones; mycobacteria; photosynthesis-inhibiting activity; chloroplasts; alga; toxicological screening; Artemia salina Quinazoline-4-thiones; mycobacteria; photosynthesis-inhibiting activity; chloroplasts; alga; toxicological screening; Artemia salina

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Kubicová, L.; Šustr, M.; Kráľová, K.; Chobot, V.; Vytlačilová, J.; Jahodář, L.; Vuorela, P.; Macháček, M.; Kaustová, J. Synthesis and Biological Evaluation of Quinazoline-4-thiones. Molecules 2003, 8, 756-769.

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