Carbonic acid 8-butoxycarbonyloxy-7-hexyl-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester butyl ester | 139565-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Carbonic acid 8-butoxycarbonyloxy-7-hexyl-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester butyl ester
• 英文别名: (8-butoxycarbonyloxy-2-hexyl-9,10-dioxoanthracen-1-yl) butyl carbonate
• CAS: 139565-52-9
• 化学式: C₃₀H₃₆O₈
• 分子量: 524.611
• InChiKey: FHUKHJJQKRNEAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  38
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,8-二甲氧基蒽醌 在 sodium hydroxide 、 sodium dithionite 、 氢溴酸 、 三乙胺 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 19.5h， 生成 Carbonic acid 8-butoxycarbonyloxy-7-hexyl-9,10-dioxo-9,10-dihydro-anthracen-1-yl ester butyl ester
  参考文献：
  名称：

  Novel anthraquinone inhibitors of human leukocyte elastase and cathepsin G

  摘要：

  A large series of variously substituted anthraquinones has been synthesized and assayed for inhibitory capacity against human leukocyte elastase (HLE) and cathepsin G (CatG), two serine proteinases implicated in diseases characterized by the abnormal degradation of connective tissue, such as pulmonary emphysema and rheumatoid arthritis. It was found that 2-alkyl-1,8-dihydroxyanthraquinone analogues are competitive inhibitors of HLE with IC50 values ranging from 4 to 10-mu-M, and also inhibit CatG with IC50 values ranging from 25 to 55-mu-M. Consequently, analogues containing the 2-alkyl-1-hydroxy-8-methoxyanthraquinone substitution pattern inhibit HLE to the same magnitude as for the compounds above, but show very little inhibition of CatG. Anthraquinones containing long, hydrophobic n-butyl carbonate moieties in the 1- and 8-positions in conjunction with a third hydrophobic substituent in the 2- or 3-position are highly selective for HLE, with K(i) values in the range of 10(-7) M. All of the inhibitors described are completely reversible, with no evidence of acyl-enzyme formation detected.

  DOI：

  10.1021/jm00087a014

文献信息

• Novel anthraquinone inhibitors of human leukocyte elastase and cathepsin G
  作者：David E. Zembower、Chih Min Kam、James C. Powers、Leon H. Zalkow

  DOI：10.1021/jm00087a014

  日期：1992.5

  A large series of variously substituted anthraquinones has been synthesized and assayed for inhibitory capacity against human leukocyte elastase (HLE) and cathepsin G (CatG), two serine proteinases implicated in diseases characterized by the abnormal degradation of connective tissue, such as pulmonary emphysema and rheumatoid arthritis. It was found that 2-alkyl-1,8-dihydroxyanthraquinone analogues are competitive inhibitors of HLE with IC50 values ranging from 4 to 10-mu-M, and also inhibit CatG with IC50 values ranging from 25 to 55-mu-M. Consequently, analogues containing the 2-alkyl-1-hydroxy-8-methoxyanthraquinone substitution pattern inhibit HLE to the same magnitude as for the compounds above, but show very little inhibition of CatG. Anthraquinones containing long, hydrophobic n-butyl carbonate moieties in the 1- and 8-positions in conjunction with a third hydrophobic substituent in the 2- or 3-position are highly selective for HLE, with K(i) values in the range of 10(-7) M. All of the inhibitors described are completely reversible, with no evidence of acyl-enzyme formation detected.