cryptotanshinone anhydride | 1426129-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: cryptotanshinone anhydride
• 英文别名: 1,2,6,7,8,9-Hexahydro-1,6,6-trimethyl-3,11-dioxanaphth[2,1-e]azulene-10,12-dione；(5R)-5,15,15-trimethyl-3,8-dioxatetracyclo[8.8.0.02,6.011,16]octadeca-1(10),2(6),11(16),17-tetraene-7,9-dione
• CAS: 1426129-68-1
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: ROYYPPPACDMYJY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  隐丹参酮 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以20%的产率得到cryptotanshinone anhydride
  参考文献：
  名称：

  Potent, Irreversible Inhibition of Human Carboxylesterases by Tanshinone Anhydrides Isolated fromSalvia miltiorrhiza(“Danshen”)

  摘要：

  The roots of Salvia miltiorrhiza ("Danshen") have been used in Chinese herbal medicine for centuries for a host of different conditions. While the exact nature of the active components of this material are unknown, large amounts of tanshinones are present in extracts derived from these samples. Recently, the tanshinones have been demonstrated to be potent human carboxylesterase (CE) inhibitors, with the ability to modulate the biological activity of esterified drugs. During the course of these studies, we also identified more active, irreversible inhibitors of these enzymes. We have purified, identified, and synthesized these molecules and confirmed them to be the anhydride derivatives of the tanshinones. These compounds are exceptionally potent inhibitors (K-i < 1 nM) and can inactivate human CEs both in vitro and in cell culture systems and can modulate the metabolism of the esterified drug oseltamivir. Therefore, the coadministration of Danshen extracts with drugs that contain the ester chemotype should be minimized since, not only is transient inhibition of CEs observed with the tanshinones, but also prolonged irreversible inhibition arises via interaction with the anhydrides.

  DOI：

  10.1021/acs.jnatprod.8b00378

文献信息

• Oxygen Insertion of <i>o</i>-Quinone under Catalytic Hydrogenation Conditions
  作者：Da-Li Zhang、Li-Yan Zhou、Jun-Min Quan、Wei Zhang、Lian-Quan Gu、Zhi-Shu Huang、Lin-Kun An

  DOI：10.1021/ol400164e

  日期：2013.3.15

  An oxygen-insertion reaction that transforms an o-quinone and a conjugated alpha-diketone substrate Into an anhydride product or derivative under catalytic hydrogenation conditions is reported. The experiments and computations indicate that the oxygen insertion proceeds via a radical mechanism mediated by an acetoxyl radical.