Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of Monogallic Acid Conjugates of Quercetin at the 3-, 7-, and 4'-Hydroxyl Groups through Selective Protection of Hydroxyl Groups

  • Jang, Jongyun (Department of Pharmaceutical Science and Technology, Natural Science Research Institute & Advanced Healthcare Industry Research Center, Catholic University of Daegu) ;
  • Kang, Dong Wook (Department of Pharmaceutical Science and Technology, Natural Science Research Institute & Advanced Healthcare Industry Research Center, Catholic University of Daegu)
  • Received : 2019.01.06
  • Accepted : 2019.01.24
  • Published : 2019.04.20
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Abstract

Keywords

JCGMDC_2019_v63n2_138_f0001.png 이미지

Figure 1. Chemical structures of EGCG, quercetin, isoquercetin, gallic acid (1) and quercetin-3-gallate (2).

JCGMDC_2019_v63n2_138_f0002.png 이미지

Scheme 1. Synthesis of quercetin-3-gallate. Reagents and reactions: (i) BnBr, K2CO3, DMF, rt, 12 h, 39%; (ii) gallic acid tribenzyl ether, EDC, DMAP, methylene chloride, 12 h, 82%; (iii) Pd/C, H2, THF/EtOH (1:1), 6 h, 60%.

JCGMDC_2019_v63n2_138_f0003.png 이미지

Scheme 2. Synthesis of quercetin-7-gallate. Reagents and reactions: (i) Ph2CCl2, Ph2O, 170 ℃, 12 h, 40%; (ii) BnBr, K2CO3, DMF, 12 h, 50%; (iii) gallic acid tribenzyl ether, EDC, DMAP, methylene chloride, rt, 52%; (iv) Pd/C, H2, THF/ EtOH (1:1), 6 h, 30%.

JCGMDC_2019_v63n2_138_f0004.png 이미지

Scheme 3. Synthesis of quercetin-4′-gallate. Reagents and reactions: (i) BnBr, K2CO3, DMF, 12 h; (ii) AcOH/ H2O (80:20), 180 ℃, 6 h, 83%; (iii) Ac2O, pyridine, 70 ℃, 3 h, 56%; (iv) BnBr, K2CO3, DMF, rt, 12 h, 35%; (v) gallic acid tribenzyl ether, EDC, DMAP, methylene chloride, rt, 12 h, 90%; (vi) Pd/C, H2, THF/ EtOH (1:1), 6 h, 41%.

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