6′-O-p-hydroxybenzoyl-6-O-p-hydroxybenzoyl-5,7-bisdeoxycynanchoside | 1423129-06-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6′-O-p-hydroxybenzoyl-6-O-p-hydroxybenzoyl-5,7-bisdeoxycynanchoside
• 英文别名: [(2R,3S,4S,5R,6S)-6-[[(1S,4aR,5R,7S,7aS)-7-hydroxy-5-(4-hydroxybenzoyl)oxy-7-(hydroxymethyl)-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxybenzoate
• CAS: 1423129-06-9
• 化学式: C₂₉H₃₂O₁₄
• 分子量: 604.565
• InChiKey: STNVRHKQTSIGBZ-DDQHOFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  222
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  6′-O-p-hydroxybenzoyl-6-O-p-hydroxybenzoyl-5,7-bisdeoxycynanchoside 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  A Chemical–Biological Study Reveals C₉-type Iridoids as Novel Heat Shock Protein 90 (Hsp90) Inhibitors

  摘要：

  The potential of heat shock protein 90 (Hsp90) as a therapeutic target for numerous diseases has made the identification and optimization of novel Hsp90 inhibitors an emerging therapeutic strategy. A surface plasmon resonance (SPR) approach was adopted to screen some iridoids for their Hsp90 alpha binding capability. Twenty-four iridoid derivatives, including 13 new natural compounds, were isolated from the leaves of Tabebuia argentea and petioles of Catalpa bignonioides. Their structures were elucidated by NMR, electrospray ionization mass spectrometry, and chemical methods. By means of a panel of chemical and biological approaches, four iridoids were demonstrated to bind Hsp90 alpha. In particular, the dimeric iridoid argenteoside A was shown to efficiently inhibit the chaperone in biochemical and cellular assays. Our results disclose C-9-type iridoids as a novel class of Hsp90 inhibitors.

  DOI：

  10.1021/jm301398y

文献信息

• A Chemical–Biological Study Reveals C₉-type Iridoids as Novel Heat Shock Protein 90 (Hsp90) Inhibitors
  作者：Fabrizio Dal Piaz、Antonio Vassallo、Abeer Temraz、Roberta Cotugno、Maria A. Belisario、Giuseppe Bifulco、Maria G. Chini、Claudio Pisano、Nunziatina De Tommasi、Alessandra Braca

  DOI：10.1021/jm301398y

  日期：2013.2.28

  The potential of heat shock protein 90 (Hsp90) as a therapeutic target for numerous diseases has made the identification and optimization of novel Hsp90 inhibitors an emerging therapeutic strategy. A surface plasmon resonance (SPR) approach was adopted to screen some iridoids for their Hsp90 alpha binding capability. Twenty-four iridoid derivatives, including 13 new natural compounds, were isolated from the leaves of Tabebuia argentea and petioles of Catalpa bignonioides. Their structures were elucidated by NMR, electrospray ionization mass spectrometry, and chemical methods. By means of a panel of chemical and biological approaches, four iridoids were demonstrated to bind Hsp90 alpha. In particular, the dimeric iridoid argenteoside A was shown to efficiently inhibit the chaperone in biochemical and cellular assays. Our results disclose C-9-type iridoids as a novel class of Hsp90 inhibitors.