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Warabhorn Rodphon Pavitra Laohapaisan Nantamon Supantanapong Onrapak Reamtong Lukana Ngiwsara Kriengsak Lirdprapamongkol Dr. Charnsak Thongsornkleeb Nisachon Khunnawutmanotham Dr. Jumreang Tummatorn Prof. Jisnuson Svasti Prof. Somsak Ruchirawat 《ChemMedChem》2021,16(24):3750-3762
Eighteen hybrid compounds between 8-bromo-2-fluoro-isocryptolepine ( 4 ) and 1,2,3-triazole were synthesized via azide rearrangement-annulation reaction. Compound 4 underwent regioselective N-propargylation and click reaction to form 8-bromo-2-fluoro-isocryptolepine-triazole hybrids 11 which were evaluated for cytotoxic activity. Compound 11 c containing 1-anisyltriazole was the most effective in inhibiting HepG2, HuCCA-1 and A549 cell lines (IC50 values of 1.65–3.07 μM) while compounds 11 a (1-phenyltriazole), 11 j (1-para-CF3-benzyltriazole) and 11 l (1-meta-Cl-benzyltriazole) were potent inhibitors of HuCCA-1, HepG2 and A549 cell lines, respectively. Moreover, 11 l showed the lowest cytotoxicity to normal human kidney cell line. Compounds 11 c and 11 l provided improvement of cytotoxic activity over 4 . Compounds 4 , 11 c and 11 l were selected to investigate their mechanisms of action. The results showed that 4 could induce G2/M cell cycle arrest and was involved in the upregulation of p53 and p21 proteins. However, the mechanisms of growth inhibition by 11 c and 11 l were associated with G0/G1 cell cycle arrest and mediated by induction of oxidative stress. 相似文献
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