Meesin, Jatuporn

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Meesin, Jatuporn
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jatuporn.me@kmitl.ac.th

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    DBU-Mediated Dimerization: Facile Access to 9,9′-Bifluorenylidenes and Isoindigos
    (2023-11-14)
    Purahong, Nitchakan
    ;
    Hongthong, Sakchai
    ;
    Chotsaeng, Nawasit
    ;
    Kuhakarn, Chutima
    ;
    Meesin, Jatuporn
    The present work describes the 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted self-dimerization of 9-chlorofluorenes and 3-chlorooxindoles for the preparation of the corresponding 9,9 -bifluorenylidene and isoindigo derivatives in moderate to good yields of 29 97%. The reactions proceed readily in a short reaction time under mild and metal-free conditions. Scale-up syntheses (5.0 mmol) of selected 9,9 -bifluorenylidene derivatives proceed in decent yields, highlighting the synthetic utility of the reported protocol.
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    Sulfonylated Indeno[1,2-c]quinoline Derivatives as Potent EGFR Tyrosine Kinase Inhibitors
    (2023-06-06)
    Hengphasatporn, Kowit
    ;
    Aiebchun, Thitinan
    ;
    Mahalapbutr, Panupong
    ;
    Auepattanapong, Atima
    ;
    Khaikate, Onnicha
    The epidermal growth factor receptor (EGFR) has been considered a potential target for lung cancer therapy due to its essential role in regulating the survival and proliferation of cancer cells. Although erlotinib, a potent EGFR tyrosine kinase (EGFR-TK) inhibitor, has been used as the first-line drug for lung cancer treatment, acquired drug resistance caused by the T790M secondary mutation of EGFR-TK inevitably develops after a median response duration of 9-13 months. Thus, the search for promising compounds to effectively target EGFR-TK has become an imperative necessity. In this study, the kinase inhibitory activities of a series of sulfonylated indeno[1,2-c]quinolines (SIQs) against EGFR-TK were experimentally and theoretically investigated. Among the 23 SIQ derivatives studied, eight compounds showed enhanced EGFR-TK inhibitory activity (IC<inf>50</inf> values of ca. 0.6-10.2 nM) compared to the known drug erlotinib (IC<inf>50</inf> of ∼20 nM). In a cell-based assay in human cancer cell lines with EGFR overexpression (A549 and A431 cells), the eight selected SIQs all showed more significant cytotoxicity against A431 than A549 cells, consistent with the higher EGFR expression in A431 cells. Molecular docking and FMO-RIMP2/PCM calculations revealed that SIQ17 occupies the ATP-binding site of EGFR-TK, where its sulfonyl group is mainly stabilized by C797, L718, and E762 residues. Triplicate 500 ns molecular dynamics (MD) simulations also confirmed the binding strength of SIQ17 in complex with EGFR. Overall, the potent SIQ compounds obtained in this work could be further optimized for developing novel anticancer drug candidates targeting EGFR-TK.
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    Synthesis of indolo- and benzothieno[3,2-c]quinolines via POCl3 mediated tandem cyclization of o-alkynylisocyanobenzenes derived from o-alkynyl-N-phenylformamides
    (2022-08-01)
    Uppalabat, Thikhamporn
    ;
    Tapdara, Anyawan
    ;
    Khaikate, Onnicha
    ;
    Worakul, Thanapat
    ;
    Surawatanawong, Panida
    A synthesis of indolo[3,2-c]quinolines and benzothieno[3,2-c]quinolines has been developed employing o-alkynyl-N-phenylformamide derivatives as the substrates. The reaction proceeded via a tandem process involving POCl<inf>3</inf>-assisted intramolecular cyclization of the firstly formed o-alkynylisocyanobenzenes, leading to the desired products in moderate to high yields. Furthermore, the reaction is efficient on a gram-scale and the products were structurally modified by amination, Suzuzki-Miyaura reaction and Heck cross-coupling. Photophysical properties of several selected indolo[3,2-c]quinolines were studied by UV-Visible and fluorescence spectroscopy and rationalized using time-dependent DFT calculations.
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    Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethyl­xanthate: Synthesis of Isoindigos
    (2022-08-17)
    Meesin, Jatuporn
    ;
    Chotsaeng, Nawasit
    ;
    Kuhakarn, Chutima
    A novel dimerization of 3-chlorooxindoles promoted by potassium ethylxanthate to access isoindigo derivatives is described. The reactions proceeded readily at room temperature in short reaction times. A mechanistic study revealed that the 3-chlorooxindole is initially converted into O-ethyl S-(2-oxo-2,3-dihydro-1H-indol-3-yl) dithiocarbonate, which subsequently undergoes dimerization with elimination of arbon disulfide. In almost all cases, analytically pure isoindigos were isolated in moderate to good yields without a requirement for chromatographic purification.
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    DBU-Mediated Reaction of 3-Chlorooxindole and 9-Xanthyl Fluorene for Synthesis of 3-Arylidene Oxindole
    (2025-04-01)
    Purahong, Nitchakan
    ;
    Teerawatananond, Thapong
    ;
    Chotsaeng, Nawasit
    ;
    Janthakit, Pattarapapa
    ;
    Nalaoh, Phattananawee
    This work reports a new route for the synthesis of 3-(9H-fluoren-9-ylidene)indolin-2-one derivatives via the reaction of 3-chlorooxindoles and O-ethyl S-(9H-fluoren-9-yl) carbonodithioates mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reactions readily proceeded at room temperature, enable a collection of 3-alkenyl oxindoles to be prepared within a short reaction time (15 minutes). The 3-alkenyl oxindoles can be easily converted to 3-fluorenyl oxindoles by NaBH<inf>4</inf> reduction.
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    Electrochemically driven reductive cyclization of o-nitroanilines: synthesis of 1,2-fused benzimidazoles and benzo[d]imidazoles
    (2025-03-31)
    Saetan, Jutamart
    ;
    Purahong, Nitchakan
    ;
    La-Ongthong, Kannika
    ;
    Hassa, Nattawoot
    ;
    Chotsaeng, Nawasit
    The electrochemical synthesis of 1,2-fused benzimidazoles and benzo[d]imidazoles from o-nitroanilines in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded through a tandem process involving nitro reduction/C(sp<sup>3</sup>)-H amination/condensation. The method can accommodate a broad range of o-nitroanilines and results in the desired products in yields of up to 99%. A plausible reaction mechanism was proposed on the basis of controlled experiments and cyclic voltammetry (CV) analysis. The benefits of the developed method include one-pot synthesis, open-air conditions, gram-scale synthesis and no requirement for a strong reductant.