deflectin 2b | 79495-63-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: deflectin 2b
• 英文别名: (6aR)-3,6a-dimethyl-9-[(2S)-2-methyldodecanoyl]furo[2,3-h]isochromene-6,8-dione
• CAS: 79495-63-9
• 化学式: C₂₆H₃₄O₅
• 分子量: 426.553
• InChiKey: VWGYSDWIZCHBOH-QLXKLKPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  deflectin 2b 、 苄胺 以 四氢呋喃 为溶剂， 反应 0.17h， 以62%的产率得到2-benzyl-3,6a-dimethyl-9-(2-methyl-dodecanoyl)-2H,6aH-furo[2,3-h]isoquinoline-6,8-dione
  参考文献：
  名称：

  Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors

  摘要：

  A series of mold metabolites of Ascomycetes, structurally belonging to the class of azaphilones, were found to inhibit the heat shock protein Hsp90. In particular, bulgarialactone B was tested for its binding to Hsp90 using surface plasmon resonance and limited proteolysis assays and for its effects on Hsp90 client proteins expression in a series of human tumor cell lines. This compound showed high affinity for Hsp90, interacting with the 90-280 region of the N-terminal domain and down-regulated the Hsp90 client proteins Raf-1, survivin, Cdk4, Akt, and EGFR. Bulgarialactone B and other natural azaphilones showed antiproliferative activity in a panel of human tumor cell lines; their conversion into semisynthetic derivatives by reaction with primary amines increased the antiproliferative activity. Preliminary results indicated in vivo activity of bulgarialactone B against an ascitic ovarian carcinoma xenograft, thus supporting the therapeutic potential of this novel series of Hsp90 inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.068