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A series of new 1,3,4‐oxadiazin‐5(6H)‐one derivatives (6a–n) of dehydroabietic acid were designed and synthesized as potential antimicrobial and antitumor agents. Their structures were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analyses. All the title compounds were evaluated for their antimicrobial activity against four bacterial and three fungal strains using the serial dilution method. Among them, compound 6e showed the highest antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) value of 1.9 μg/mL. In addition, the in vitro cytotoxic activities of the title compounds were also assayed against three human carcinoma cell lines (MCF‐7, SMMC‐7721, and HeLa) through the MTT colorimetric method. As a result, compounds 6b, 6g, 6k, and 6m exhibited significant inhibition against at least one cell line with IC50 values below 10 μM. Compound 6m was especially found to be the most potent derivative with IC50 values of 2.26 ± 0.23, 0.97 ± 0.11, and 1.89 ± 0.31 μM against MCF‐7, SMMC‐7721, and HeLa cells, respectively, comparable to positive control etoposide. [ABSTRACT FROM AUTHOR]

Abstract: A series of new N-substituted 1H-dibenzo[a,c]carbazole derivatives were synthesized from dehydroabietic acid, and their structures were characterized by IR, 1H NMR and HRMS spectral data. All compounds were evaluated for their antibacterial and antifungal activities against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Candida albicans, Candida tropicalis and Aspergillus niger) by serial dilution technique. Some of the synthesized compounds displayed pronounced antimicrobial activity against tested strains with low MIC values ranging from 0.9 to 15.6μg/ml. Among them, compounds 6j and 6r exhibited potent inhibitory activity comparable to reference drugs amikacin and ketoconazole. [Copyright &y& Elsevier]

A series of new 1 H -benzo[ d ]imidazole derivatives of dehydroabietic acid were designed and synthesized as potent antitumor agents. Structures of the target molecules were characterized using MS, IR, 1 H NMR, 13 C NMR and elemental analyses. In the in vitro cytotoxic assay, most compounds showed significant cytotoxic activities against two hepatocarcinoma cells (SMMC-7721 and HepG2) and reduced cytotoxicity against noncancerous human hepatocyte (LO2). Among them, compound 7b exhibited the best cytotoxicity against SMMC-7721 cells (IC 50 : 0.36 ± 0.13 μM), while 7e was most potent to HepG2 cells (IC 50 : 0.12 ± 0.03 μM). The cell cycle analysis indicated that compound 7b caused cell cycle arrest of SMMC-7721 cells at G2/M phase. Further, compound 7b also induced the apoptosis of SMMC-7721 cells in Annexin V-APC/7-AAD binding assay. [ABSTRACT FROM AUTHOR]

• Dehydroabietate-based fluorescent probe for Hg2+ and Fe3+ was synthesized and characterized. • Detection limits of the sensor were 31.0 nM and 31.2 nM for Hg2+ and Fe3+ ions, respectively. • The sensor have a wide pH range for ion detection (5 ~ 12), and a short response time (10 s). • Fluorescent imaging experiments using MCF-7 and SMCC-7721 cell were carried out successfully. A novel dehydroabietic acid-based fluorescent probe (DBH) containing 2,4-diarylbenzimidazole moiety was designed and synthesized, and the compound was characterized by its UV–Vis, FT-IR, 1H NMR, 13C NMR and ESI-MS spectra. DBH could be used for the detection of Fe3+ and Hg2+ through the selective fluorescence quenching in EtOH/H 2 O solution. The probe DBH showed excellent selectivity and sensitivity towards Fe3+ and Hg2+ over other metal ions. The limits of detection were calculated as 3.12 × 10−8 M and 3.10 × 10−8 M, respectively. Especially, DBH have a wide pH range for ion detection (5 ~ 12), and a short response time (10 s). Job's plot method in combination with ESI-MS and FT-IR spectra was used to determine the stoichiometry of DBH -Fe3+/Hg2+ complexes as both 2:1. Moreover, DBH exhibited low cytotoxicity to MCF-7 and SMCC-7721 cells (IC 50 > 100 μM). In the fluorescent cell imaging experiments, DBH could be used as a prominent intracellular probe for the detection of Fe3+ and Hg2+ in living cells. [ABSTRACT FROM AUTHOR]