- Synthesis, crystal structure and photoluminescence of 3-(1-benzotriazole)-4-methyl-coumarin
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A novel coumarin derivative containing an electron-transporting moiety (benzotriazole), 3-(1-benzotriazole)-4-methyl-coumarin (BMC), was synthesized from starting substances, i.e. benzotriazole and 2-hydroxyacetophenone. The compound structure was verified by FT-IR, 1H NMR, element analysis and single crystal X-ray crystallography. Crystallographic data reveal a dihedral angle of 108° between the coumarin and benzotriazole rings, which is attributed to the spatial hindrance of a 4-positioned methyl group. The fluorescence and UV-vis absorption of BMC were discussed. The compound exhibits a strong UV emission peak at 385 nm under 360 nm excitation. The molecular structure of BMC was optimized using density functional theory (DFT) at B3LYP/6-31G(d) level, showing that the optimized geometric parameters are in good agreement with experimental data. In addition, the HOMO and LUMO levels of BMC were deduced.
- Yu, Tianzhi,Zhao, Yuling,Fan, Duowang
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- Synthesis and cytotoxic activity of coumarin derivatives containing benzotriazole moieties
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Three coumarin derivatives containing benzotriazole moieties, 3-(1-benzotriazolyl)-4-methyl-coumarin (BMC), 3-(1-benzotriazolyl)-4-methyl- benzo[7,8]coumarin (BMBC), and 3-(4-methyl-1-benzotriazolyl)-4-methyl-benzo[7,8] coumarin (MBMBC), were synthesized. Among them, 3-(4-methyl-1-benzotriazolyl)-4- methyl-benzo[7,8]coumarin has been structurally characterized by X-ray crystallography. The cytotoxic effect by Sulforhodamine B (SRB) assay with these compounds against the human hepatocellular carcinoma cell lines (HepG-2) was carried out in vitro. The preliminary results showed that all compounds inhibit HepG-2 growth effectively. Taylor & Francis Group, LLC.
- Yu, Tianzhi,Zhang, Peng,Zhao, Yuling,Zhang, Hui,Fan, Duowang,Dong, Wenkui,Ding, Lan
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experimental part
p. 2655 - 2663
(2010/04/05)
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