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Here, we demonstrate that the first example of harmaline scaffolds serving as acceptor/acceptor-based N-C-C synthons triggered the ring opening and skeletal reconstruction of 3-vinyl benzofuranones for the construction of a library of skeletally diverse polycyclic harmaline scaffolds. These products were smoothly afforded in up to 77% yield, 420: 1 dr under catalyst-free conditions, and expanded the chemical space of biologically significant harmaline derivative species. All synthetic compounds showed cytotoxic activity against tumor cells, especially compound 3at, which exhibited selective cytotoxicity against A549 cells and lower cytotoxicity against normal cells MRC-5 and HK-2. In further mechanism research, 3at inhibited A549 cell proliferation through the G1 phase arrest, induced A549 cell apoptosis through internal and external apoptosis pathways, and suppressed the migration and invasion abilities of A549 cells. These data indicated that compound 3at is the most effective compound in the series and can serve as a promising precursor for drug development. [ABSTRACT FROM AUTHOR]

• A D-p-A type probe has been developed for detection of ClO−. • The mechanism associated with oxidation breakage of rhodanine moiety was proposed. • The crystal structure of the probe is reported. • The probe has been successfully applied to the imaging of ClO− in cells, plants and zebrafish. Hypochlorite (ClO−) plays an important role in many cellular processes, which is proved to be related to some serious diseases. Given the electron donating and electron withdrawing properties of benzo[ h ]chromene and rhodanine groups, respectively, we developed a Donor (D)-p-Acceptor (A) type probe 1 for the detection of ClO− based on benzo[ h ]chromene (D) and rhodanine (A), whose structure was determined by ESI-MS, NMR and X-ray diffraction. Probe 1 showed a fast (within 20 s), selective and sensitive response toward ClO− via a fluorescent turn-on output. Based-on the spectral change of probe 1 induced by ClO−, the mechanism associated with oxidation breakage of rhodanine moiety was proposed. Due to the excellent biocompatibility and low cytotoxicity, probe 1 can be used for imaging of ClO− in C6 cells, Arabidopsis thaliana, and zebrafish. [Display omitted] [ABSTRACT FROM AUTHOR]