2-Oxo-1,2-dihydrocyclopentazulen | 52711-37-2

• 英文名称: 2-Oxo-1,2-dihydrocyclopentazulen
• 英文别名: 1,2-Dihydrocyclopent azulen-2-on；tricyclo[5.4.1.04,12]dodeca-1(11),4(12),5,7,9-pentaen-3-one
• CAS: 52711-37-2
• 化学式: C₁₂H₈O
• 分子量: 168.195
• InChiKey: YHMQPSCWOVBCSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-Oxo-1,2-dihydrocyclopentazulen 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (4aE,8Z)-5-(diethylamino)-6-methylcyclonona[cd]pentalen-2(1H)-one
  参考文献：
  名称：

  Betulinic Acid Inhibits Growth Factor-induced in vitro Angiogenesis via the Modulation of Mitochondrial Function in Endothelial Cells

  摘要：

  Betulinic acid (BetA), a pentacyclic triterpene, is a selective apoptosis‐inducing agent that works directly in mitochondria. Recent study has revealed that BetA inhibits in vitro enzymatic activity of aminopeptidase N (APN, EC 3.4.11.2), which is known to play an important role in angiogenesis, but the anti‐angiogenic activity of BetA has not been reported yet. Data presented here show that BetA potently inhibited basic fibroblast growth factor (bFGF)‐induced invasion and tube formation of bovine aortic endothelial cells (BAECs) at a concentration which had no effect on the cell viability. To access whether the anti‐angiogenic nature of BetA originates from its inhibitory action against aminopeptidase N (APN) activity, the effect of BetA on APN was investigated. Surprisingly, BetA did not inhibit in vivo APN activity in endothelial cells or APN‐positive tumor cells. On the other hand, BetA significantly decreased the mitochondrial reducing potential, and treatment with mitochondrial permeability transition (MPT) inhibitors attenuated BetA‐induced inhibition of endothelial cell invasion. These results imply that anti‐angiogenic activity of BetA occurs through a modulation of mitochondrial function rather than APN activity in endothelial cells.

  DOI：

  10.1111/j.1349-7006.2002.tb01273.x
• 作为产物：
  描述：

  1-diazocyclopentazulene-2-one 生成 2-Oxo-1,2-dihydrocyclopentazulen
  参考文献：
  名称：

  Mechanistic studies on the Wolff rearrangement: the chemistry and spectroscopy of some .alpha.-keto carbenes

  摘要：

  DOI：

  10.1021/ja00311a063

文献信息

• Hafner,K. et al., Angewandte Chemie, 1974, vol. 86, # 6, p. 235 - 236
  作者：Hafner,K. et al.

  DOI：——

  日期：——
• HAFNER, K.;GOLTZ, M., ANGEW. CHEM., 1982, 94, N 9, 711
  作者：HAFNER, K.、GOLTZ, M.

  DOI：——

  日期：——