katacine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: katacine
• 英文别名: LDN-0097979；(2R,3R,4S)-2-(3,4,5-trihydroxyphenyl)-4-[(2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-8-yl]-8-[(2R,3R,4R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• 化学式: C₄₅H₃₈O₂₁
• 分子量: 914.784
• InChiKey: NVTLDVSBUJGIAD-GHFVFVICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  66
• 可旋转键数：
  5
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  392
• 氢给体数：
  18
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  katacine 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以31%的产率得到
  参考文献：
  名称：

  Synthesis of epigallocatechin trimer, (epigallocatechin)2-epicatechin, and (epigallocatechin)2-catechin via a Lewis acid mediated one-pot condensation and their antitumor activities in prostate cancer cells

  摘要：

  Syntheses of epigallocatechin trimer, (epigallocatechin)(2)-epicatechin and (epigallocatechin)(2)-catechin were achieved. The key condensation to form the proanthocyanidin trimer derivatives was accomplished in a one-pot procedure using a dimeric epigallocatechin electrophile, which was prepared in situ by self-condensation of an epigallocatechin derivative, and an epigallocatechin, epicatechin, or catechin derivative as the nucleophile in the presence of a Lewis acid. The epigallocatechin monomer to trimer compounds containing a pyrogallol group significantly suppressed cell proliferation in PC-3 prostate cancer cells. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.04.089
• 作为产物：
  描述：

  在 20% palladium hydroxide-activated charcoal 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以81%的产率得到katacine
  参考文献：
  名称：

  Synthesis of epigallocatechin trimer, (epigallocatechin)2-epicatechin, and (epigallocatechin)2-catechin via a Lewis acid mediated one-pot condensation and their antitumor activities in prostate cancer cells

  摘要：

  Syntheses of epigallocatechin trimer, (epigallocatechin)(2)-epicatechin and (epigallocatechin)(2)-catechin were achieved. The key condensation to form the proanthocyanidin trimer derivatives was accomplished in a one-pot procedure using a dimeric epigallocatechin electrophile, which was prepared in situ by self-condensation of an epigallocatechin derivative, and an epigallocatechin, epicatechin, or catechin derivative as the nucleophile in the presence of a Lewis acid. The epigallocatechin monomer to trimer compounds containing a pyrogallol group significantly suppressed cell proliferation in PC-3 prostate cancer cells. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2018.04.089

文献信息

• Synthesis of epigallocatechin trimer, (epigallocatechin)2-epicatechin, and (epigallocatechin)2-catechin via a Lewis acid mediated one-pot condensation and their antitumor activities in prostate cancer cells
  作者：Mikihiro Ichikawa、Shinya Yamamoto、Chisato Ishihara、Shuhei Nonobe、Yasunao Hattori、Koji Umezawa、Hiroshi Fujii、Hidefumi Makabe

  DOI：10.1016/j.tet.2018.04.089

  日期：2018.7

  Syntheses of epigallocatechin trimer, (epigallocatechin)(2)-epicatechin and (epigallocatechin)(2)-catechin were achieved. The key condensation to form the proanthocyanidin trimer derivatives was accomplished in a one-pot procedure using a dimeric epigallocatechin electrophile, which was prepared in situ by self-condensation of an epigallocatechin derivative, and an epigallocatechin, epicatechin, or catechin derivative as the nucleophile in the presence of a Lewis acid. The epigallocatechin monomer to trimer compounds containing a pyrogallol group significantly suppressed cell proliferation in PC-3 prostate cancer cells. (C) 2018 Elsevier Ltd. All rights reserved.