1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl 4-hydroxybenzoate | 1392502-57-6

• 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: 1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl 4-hydroxybenzoate
• 英文别名: (1,6,6-trimethyl-10,11-dioxo-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-9-yl) 4-hydroxybenzoate
• CAS: 1392502-57-6
• 化学式: C₂₆H₂₂O₆
• 分子量: 430.457
• InChiKey: MUNCXACQSGLKIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丹参酮 IIA 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl 4-hydroxybenzoate
  参考文献：
  名称：

  Design, synthesis and vasodilative activity of tanshinone IIA derivatives

  摘要：

  A new series of tanshinone IIA (DIIA) derivatives were synthesized through the reaction of brominated tanshinone IIA (1-Br DIIA) and aromatic acids in the presence of K2CO3. Twenty compounds were synthesized, and all of them were novel. Vasodilative activities for synthesized compounds were valuated in vitro on the contractile response of vascular thoracic aorta smooth muscle from Wistar rats. The results showed that most compounds exhibited a concentration-dependent inhibition on the contractile response of norepinephrine. Four prepared compounds, 4, 5, 8 and 13 revealed relatively remarkable vasodilative activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.014

文献信息

• Design, synthesis and biological evaluation of tanshinone IIA derivatives as NLRP3 inflammasome inhibitors
  作者：Hao Chen、Hu Yue、Yuyun Yan、Nannan Wu、Dan Wu、Ping Sun、Wenhui Hu、Zhongjin Yang

  DOI：10.1016/j.bmcl.2024.129725

  日期：2024.5

  moderately inhibitory activity in NLRP3 inflammasome/IL-1β pathway. Herein, we designed a series of derivatives on different regions of Tanshinone IIA (TNA) scaffold. The biological evaluation identified compound , a scaffold hybrid of TNA and salicylic acid, as a potent NLRP3 inflammasome inhibitor. Mechanistically, inhibits the production of ROS and prevents NLRP3 inflammasome-dependent IL-1β production

  天然产物结构长期以来一直为药物发现提供有价值的药效基团甚至候选物。丹参酮支架对 NLRP3 炎症小体/IL-1β 通路表现出中等抑制活性。在此，我们在丹参酮IIA（TNA）支架的不同区域设计了一系列衍生物。生物学评估确定化合物（TNA 和水杨酸的支架杂化物）是一种有效的 NLRP3 炎症小体抑制剂。从机制上讲，抑制 ROS 的产生并阻止 NLRP3 炎性体依赖性 IL-1β 的产生。此外，治疗可显着减弱 DSS 诱发的腹膜炎的炎症反应。我们的工作描述了一种潜在的丹参酮衍生物，其结构需要进一步优化，作为治疗炎症性疾病的 NLRP3 炎性体抑制剂。
• Design, synthesis and vasodilative activity of tanshinone IIA derivatives
  作者：Yue-Feng Bi、Zhen-Ji Wang、Ruo-Fei Guan、Yu-Ting Ye、Yuan-Yuan Chen、Yan-Bing Zhang、Hong-Min Liu

  DOI：10.1016/j.bmcl.2012.05.014

  日期：2012.8

  A new series of tanshinone IIA (DIIA) derivatives were synthesized through the reaction of brominated tanshinone IIA (1-Br DIIA) and aromatic acids in the presence of K2CO3. Twenty compounds were synthesized, and all of them were novel. Vasodilative activities for synthesized compounds were valuated in vitro on the contractile response of vascular thoracic aorta smooth muscle from Wistar rats. The results showed that most compounds exhibited a concentration-dependent inhibition on the contractile response of norepinephrine. Four prepared compounds, 4, 5, 8 and 13 revealed relatively remarkable vasodilative activity. (C) 2012 Elsevier Ltd. All rights reserved.