title: Synthesis and antimycobacterial and photosynthesis-inhibiting evaluation of 2-[(E)-2-substituted-ethenyl]-1,3-benzoxazoles.
abstract: A series of twelve 2-[(E)-2-substituted-ethenyl]-1,3-benzoxazoles was designed. All the synthesized compounds were tested against three mycobacterial strains. The compounds were also evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. 2-[(E)-2-(4-Methoxyphenyl)ethenyl]-1,3-benzoxazole, 2-[(E)-2-(2,3-dihydro-1-benzofuran-5-yl)ethenyl]-1,3-benzoxazole and 2-{(E)-2-[4-(methylsulfanyl)phenyl]ethenyl}-1,3-benzoxazole showed the highest activity against M. tuberculosis, M. kansasii, and M. avium, and they demonstrated significantly higher activity against M. avium and M. kansasii than isoniazid. The PET-inhibiting activity of the most active ortho-substituted compound 2-[(E)-2-(2-methoxyphenyl)ethenyl]-1,3-benzoxazole was IC₅₀ = 76.3 μmol/L, while the PET-inhibiting activity of para-substituted compounds was significantly lower. The site of inhibitory action of tested compounds is situated on the donor side of photosystem II. The structure-activity relationships are discussed.
authors.affiliation: Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic.
authors.forename: Ales
authors.initials: A
authors.lastname: Imramovsky
authors.affiliation: Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic ; Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic.
authors.forename: Jan
authors.initials: J
authors.lastname: Kozic
authors.affiliation: Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia.
authors.forename: Matus
authors.identifier: 0000-0003-1421-3384
authors.initials: M
authors.lastname: Pesko
authors.affiliation: Laboratory for Mycobacterial Diagnostics and TB, Institute of Public Health in Ostrava, Partyzanske namesti 7, 702 00 Ostrava, Czech Republic.
authors.forename: Jirina
authors.initials: J
authors.lastname: Stolarikova
authors.affiliation: Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic.
authors.forename: Jarmila
authors.initials: J
authors.lastname: Vinsova
authors.affiliation: Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia.
authors.forename: Katarina
authors.identifier: 0000-0003-2785-8077
authors.initials: K
authors.lastname: Kralova
authors.affiliation: Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackeho 1/3, 612 42 Brno, Czech Republic.
authors.forename: Josef
authors.identifier: 0000-0003-2003-9052
authors.initials: J
authors.lastname: Jampilek
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002736:Chloroplasts / Q000378:metabolism; D004579:Electron Transport / Q000187:drug effects; D020128:Inhibitory Concentration 50; D009159:Mycobacteriaceae / Q000187:drug effects*; D010788:Photosynthesis / Q000187:drug effects*; D013045:Species Specificity; D018724:Spinacia oleracea; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D001583:Benzoxazoles