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Chemistry and Industry of Forest Products ›› 2016, Vol. 36 ›› Issue (6): 41-48.doi: 10.3969/j.issn.0253-2417.2016.06.007

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Synthesis of Isolongifolanyl Thiazole Compounds and Their Antibacterial and Antitumor Activities

RUI Jian1, YANG Jin-lai1, CAI Tao1, XU Xu1,2, WANG Shi-fa1,2   

  1. 1. College of Chemical Engineering, Jiangsu Key Laboratory of Biomass Green Fuels and Chemicals, Nanjing 210037, China;
    2. Jiangsu Key Laboratory of Biomass Energy and Material, Nanjing 210042, China
  • Received:2015-11-19 Online:2016-12-25 Published:2016-12-23

Abstract: Eleven new kinds of isolongifolanyl thiazole compounds were synthesized by condensation, nucleophilic substitution and cyclization from isolongifolenone. The structures of the target compounds were characterized by 1H NMR, 13C NMR, LC-MS and FT-IR, respectively. Antibacterial evaluation of the compounds was carried out by minimum inhibitory concentrations assay (MIC). The results showed that the antibacterial activities of (E)-4-(4-methoxyphenyl)-2-(2-(1,1,5,5-tetramethyl-3,4,5,6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)thiazole(2e) and (E)-2-(2-(1,1,5,5-tetramethyl-3,4,5,6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)-4-(p-tolyl) thiazole (2g) were better than those of others against Escherichia coli and Staphylococcus aureus. Their MIC were 7.8 mg/L. The antibacterial activity of (E)-4-(4-chlorophenyl)-2-(2-(1,1,5,5-tetramethyl-3,4,5,6-tetrahydro-1H-2,4a-methanonaphthalen-7(2H)-ylidene)hydrazinyl)thiazole (2b) was better than those of others against fungus. Its MIC value aganist Candida albicans and Candida tropicalis was 15.6 mg/L. Their antitumor activities against HepG2 were evaluated by thiazole blue test(MTT). Compound 2g (IC50=43.9±0.9 mg/L) was found to be the most potent derivative overall the tested compounds against HepG2.

Key words: isolongifolenone, thiazole compounds, antibacterial activity, antitumor activity

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