Demethoxydebromoaplysiatoxin | 1446754-13-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: Demethoxydebromoaplysiatoxin
• 英文别名: (1S,3R,4S,5S,9R,13S,14R)-13-hydroxy-9-[(1R)-1-hydroxyethyl]-3-[(2S)-5-(3-hydroxyphenyl)pentan-2-yl]-4,14,16,16-tetramethyl-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione
• CAS: 1446754-13-7
• 化学式: C₃₁H₄₆O₉
• 分子量: 562.701
• InChiKey: XSJFPSCYMJFDNI-QGKMEOSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  debromo aplysiatoxin 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 Demethoxydebromoaplysiatoxin
  参考文献：
  名称：

  JP6170908

  摘要：

  公开号：

文献信息

• JP6170908
  申请人：——

  公开号：——

  公开（公告）日：——
• Effects of the methoxy group in the side chain of debromoaplysiatoxin on its tumor-promoting and anti-proliferative activities
  作者：Ryo C. Yanagita、Hiroaki Kamachi、Masayuki Kikumori、Harukuni Tokuda、Nobutaka Suzuki、Kiyotake Suenaga、Hiroshi Nagai、Kazuhiro Irie

  DOI：10.1016/j.bmcl.2013.05.096

  日期：2013.8

  Debromoaplysiatoxin (DAT) is a tumor promoter isolated from sea hare and exhibits anti-proliferative activity against several cancer cell lines. To clarify key residues that are responsible for its tumor-promoting activity, we focused on the chiral methoxy group in the side chain, whose role had not yet been discussed or examined before. Demethoxy-DAT (8) was derived from DAT and we evaluated its tumor-promoting activity, anti-proliferative activity, and ability to bind to protein kinase C (PKC) isozymes. Compound 8 showed somewhat weaker tumor-promoting activity than that of DAT both in vitro and in vivo, but showed higher anti-proliferative activity against several cancer cell lines. Although the affinity to novel PKC isozymes of 8 was comparable to that of DAT, the affinity to conventional PKC isozymes decreased slightly. These results suggest that the methoxy group of DAT is one of the key residues critical for tumor-promoting activity but not for anti-proliferative activity. Since the methoxy group has little influence on the molecular hydrophobicity, this is the first report showing that structural factors other than hydrophobicity in the side chain of DAT affected its biological activities. (C) 2013 Elsevier Ltd. All rights reserved.