Synthesis and photosynthetic inhibition activity of substituted 5-(bis-trifluoromethyl)methyl)-2-aminothiazoles

• Published in: Journal of fluorine chemistry Vol. 127; no. 11; pp. 1522 - 1527
• Main Authors: Boyer, Cécile, Finazzi, Giovanni, Laurent, Philippe, Haas, Alois, Blancou, Hubert
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.11.2006; Elsevier
• Subjects: 2-Aminothiazole; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; DCMU; Fluorescence; Gem bis-trifluoromethylated molecules; Lipophilicity; Physical Sciences; PS II inhibitor; Science & Technology; Fluorescence; DCMU; 2-Aminothiazole; PS II inhibitor; Gem bis-trifluoromethylated molecules; Lipophilicity; ACID; PARTITION-COEFFICIENTS; fluorescence; 2-aminothiazole; PSII inhibitor; lipophilicity; CYCLIC PEPTIDE DOLASTATIN-3; gem bis-trifluoromethylated molecules
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2006.07.007

The reaction of 5,5,5-trifluoro-4-trifluoromethyl-pent-3-en-2-one with aminothiocarbonyls yielded aminothiourea precursors which readily cyclised to the corresponding thiazole derivatives, 5-(bis-trifluoromethyl)methyl)-2-aminothiazoles. The inhibitory potency of photosystem II activity of these thiazoles was evaluated using fluorescence measurement techniques. Two of the compounds showed a good activity in comparison with the reference compound DCMU, 3-(3,4-dichlorophenol)-1,1-dimethylurea. Calculation of lipophilicity according to Rekker and Frey, and a corresponding experimental determination are reported. New substituted 5-(bis-trifluoromethyl)methyl)-2-aminothiazoles were prepared and their inhibiting photosystem II (PS II) activity were tested by fluorescence measurement. Two of them show a good activity, compared with that of DCMU, one of the best PS II inhibitors known. Calculation and determination of lipophilicity according to Rekker and Frey are also described. ▪