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Synthesis,Crystal Structure and Antineoplasmic Activity of 3,6,8-Tribromo-5-hydroxy-2,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one

Synthesis, Crystal Structure and Antineoplasmic Activity of 3,6,8-Tribromo-5-hydroxy-2,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
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摘要 The reaction of 5-hydroxyl-7-methoxyflavone(tectochrysin) with bromine obtained 3,6,8-tribromo-5-hydroxy-2,7-dimethoxy-2,3-dihydrochromen-4-one(1), which was characterized by FT-IR, 1 H-NMR, 13C-NMR, elemental analysis and X-ray single-crystal diffraction. Complex 1 belongs to the monoclinic system, space group pbca with a = 9.4673(8), b = 17.9938(15), c = 21.2004(17) A, V = 3611.5(5) A3, Z = 8, μ = 0.6726 mm^(-1), Dc = 1.795 g/cm3, F(000) = 2080, the final R = 0.0358 and wR = 0.0644 with I 2σ(I). The results show that the addition reaction occurs at the carbon-carbon double bond(C2 and C3) of tectochrysin and 1 belongs to dihydroflavone. The reaction mechanism was discussed and the structure revealed that the crystal structure of 1 is stabilized by intramolecular hydrogen bonds and C–Br···π interactions. The antitumor ability of 1 was evaluated against human leukemia cells(K562), human breast cancer cells(MCF-7) and human lung cancer cells(A549). 1 exhibited potent antitumor activities against human leukemia cells(K562) with the IC50 values of 18.9 μmol/L. The reaction of 5-hydroxyl-7-methoxyflavone(tectochrysin) with bromine obtained 3,6,8-tribromo-5-hydroxy-2,7-dimethoxy-2,3-dihydrochromen-4-one(1), which was characterized by FT-IR, 1 H-NMR, 13C-NMR, elemental analysis and X-ray single-crystal diffraction. Complex 1 belongs to the monoclinic system, space group pbca with a = 9.4673(8), b = 17.9938(15), c = 21.2004(17) A, V = 3611.5(5) A3, Z = 8, μ = 0.6726 mm^(-1), Dc = 1.795 g/cm3, F(000) = 2080, the final R = 0.0358 and wR = 0.0644 with I 2σ(I). The results show that the addition reaction occurs at the carbon-carbon double bond(C2 and C3) of tectochrysin and 1 belongs to dihydroflavone. The reaction mechanism was discussed and the structure revealed that the crystal structure of 1 is stabilized by intramolecular hydrogen bonds and C–Br···π interactions. The antitumor ability of 1 was evaluated against human leukemia cells(K562), human breast cancer cells(MCF-7) and human lung cancer cells(A549). 1 exhibited potent antitumor activities against human leukemia cells(K562) with the IC50 values of 18.9 μmol/L.
出处 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2018年第7期1071-1077,共7页 结构化学(英文)
基金 supported by Youth Backbone Teachers Project Funded by Xianyang Normal University(No.XSYGG201606) Scientific Research Program Funded by Shaanxi Provincial Education Department(No.16JK1822) Natural Science Basic Research Plan Funded by Shaanxi Province of China(No.2016JM5024) Science and Technology Projects of Xianyang City(No.2017k02-19) University Students Research and Innovation Training Program of Xianyang Normal University(No.2017060&201710722003) University Students Research and Innovation Training Program of Shaanxi Province(No.2490)
关键词 3 6 8-tribromo-5-hydroxy-2 7-dimethoxy-2 3-dihydrochromen-4-one spectroscopic property crystal structure reaction mechanisms antitumor activity 3,6,8-tribromo-5-hydroxy-2,7-dimethoxy-2,3-dihydrochromen-4-one spectroscopic property crystal structure reaction mechanisms antitumor activity
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