Total synthesis of 2′,4′,6′ -trimethoxy-3′,5′- dimethylchalcone derivatives

被引:1
|
作者
Park, Rae Yeon [1 ]
Lee, Hana [1 ]
Park, Kwangyong [1 ]
机构
[1] Chung Ang Univ, Sch Chem Engn & Mat Sci, 84 Heukseok Ro, Seoul 06974, South Korea
关键词
2; 4; 6; '-trimethoxy-3; 5; '-dimethylchalcone; antidiabetic compounds; chalcone derivatives; dimethyl cardamonin; total synthesis; FLAVONOIDS; INDUCTION; CHALCONE; 2'; 4'-DIHYDROXY-6'-METHOXY-3'; 5'-DIMETHYLCHALCONE; APOPTOSIS; CELLS;
D O I
10.1002/bkcs.12515
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
2',4'-Dihydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC), which is isolated from plants, has recently attracted much attention due to its beneficial pharmacological effects. The preparation of twelve 2',4',6'-trimethoxy-3',5' -dimethylchalcone (DMDMC) derivatives, which are dimethylated-derivatives of DMC, is reported herein for the first time. Our synthetic method allowed the efficient construction of the DMDMC derivatives from phloroglucinol in 37.8%-46.5% overall yields. This promising approach would be advantageous for the production of many different DMDMC derivatives in a short period of time.
引用
收藏
页码:731 / 738
页数:8
相关论文
共 50 条
  • [31] Synthesis of 5,6,7-trimethoxy-2-(4-methylphenyl)-1-(2H) phthalazinone-4-carboxamides
    Patankar, JA
    Verma, RS
    Athalye, SS
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 5 (03) : 239 - 240
  • [32] Design, synthesis, and preliminary biological evaluation of 3′,4′,5′-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents
    Deng, Xiangping
    Liu, Renbo
    Li, Junjian
    Li, Zhongli
    Liu, Juan
    Xiong, Runde
    Lei, Xiaoyong
    Zheng, Xing
    Xie, Zhizhong
    Tang, Guotao
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (04) : 1874 - 1884
  • [33] In vitro and in vivo reversal of cancer cell multidrug resistance by 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone
    Qian, F
    Ye, CL
    Wei, DZ
    Lu, YH
    Yang, SL
    JOURNAL OF CHEMOTHERAPY, 2005, 17 (03) : 309 - 314
  • [34] PREPARATION OF DERIVATIVES OF 5,6,7-TRIMETHOXY 1-HEXAHYDROPHENANTHRENONE
    TOCHTERMANN, W
    LEBOUC, A
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1975, 280 (05): : 301 - 303
  • [36] In vivo antitumor activity by 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone in a solid human carcinoma xenograft model
    Chun-Lin Ye
    Jian-Wen Liu
    Dong-Zhi Wei
    Yan-Hua Lu
    Feng Qian
    Cancer Chemotherapy and Pharmacology, 2005, 56 : 70 - 74
  • [37] SYNTHESIS OF DIVICINE (2-4-DIAMINO-5-6-DIHYDROXYPYRIMIDINE) AND OTHER DERIVATIVES OF 4-5(5-6)-DIHYDROXYPYRIMIDINE
    DAVOLL, J
    LANEY, DH
    JOURNAL OF THE CHEMICAL SOCIETY, 1956, (JUL): : 2124 - 2131
  • [38] Hepatoprotective Effects of 2′,4′-Dihydroxy-6′-methoxy-3′,5′-dimethylchalcone on CCl4-Induced Acute Liver Injury in Mice
    Yu, Wan-Guo
    Qian, Jie
    Lu, Yan-Hua
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2011, 59 (24) : 12821 - 12829
  • [39] Induction of apoptosis in K562 human leukemia cells by 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone
    Ye, CL
    Qian, F
    Wei, DZ
    Lu, YH
    Liu, JW
    LEUKEMIA RESEARCH, 2005, 29 (08) : 887 - 892
  • [40] In vivo antitumor activity by 2′,4′-dihydroxy-6′-methoxy-3′,5′-dimethylchalcone in a solid human carcinoma xenograft model
    Ye, CL
    Liu, JW
    Wei, DZ
    Lu, YH
    Qian, F
    CANCER CHEMOTHERAPY AND PHARMACOLOGY, 2005, 56 (01) : 70 - 74