1,6,6-trimethyl-11-(4-methoxyphenyl)-7,8,9,10-tetrahydro-6H-furo[2',3':1,2]phenanthro[3,4-d]imidazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1,6,6-trimethyl-11-(4-methoxyphenyl)-7,8,9,10-tetrahydro-6H-furo[2',3':1,2]phenanthro[3,4-d]imidazole
• 英文别名: 9-(4-Methoxyphenyl)-5,17,17-trimethyl-3-oxa-8,10-diazapentacyclo[10.8.0.02,6.07,11.013,18]icosa-1(12),2(6),4,7(11),9,13(18),19-heptaene；9-(4-methoxyphenyl)-5,17,17-trimethyl-3-oxa-8,10-diazapentacyclo[10.8.0.02,6.07,11.013,18]icosa-1(12),2(6),4,7(11),9,13(18),19-heptaene
• 化学式: C₂₇H₂₆N₂O₂
• 分子量: 410.516
• InChiKey: SPMZJLJERLLRDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丹参酮 IIA 、 4-甲氧基苯甲醛 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 1,6,6-trimethyl-11-(4-methoxyphenyl)-7,8,9,10-tetrahydro-6H-furo[2',3':1,2]phenanthro[3,4-d]imidazole
  参考文献：
  名称：

  高效液相色谱-柱前衍生化-高效液相色谱-荧光检测法测定丹参（丹参）中的丹参酮。

  摘要：

  丹参酮是传统草药丹参（Salvia miltiorrhiza）中的主要生物活性成分。丹参酮的灵敏可靠的测定方法对于确保丹参的质量很有用。

  DOI：

  10.1002/pca.2719

文献信息

• Determination of Tanshinones in Danshen (<i>Salvia miltiorrhiza</i> ) by High-Performance Liquid Chromatography with Fluorescence Detection after pre-Column Derivatisation
  作者：Naoya Kishikawa、Akiko Yamanouchi、Mahmoud Hamed El-Maghrabey、Kaname Ohyama、Naotaka Kuroda

  DOI：10.1002/pca.2719

  日期：2018.1

  Tanshinones are a major class of bioactive ingredients in the traditional herbal medicines, Danshen (Salvia miltiorrhiza). A sensitive and reliable determination method for tanshinones is useful to ensure the quality of Danshen.

  丹参酮是传统草药丹参（Salvia miltiorrhiza）中的主要生物活性成分。丹参酮的灵敏可靠的测定方法对于确保丹参的质量很有用。
• Tanshinone-IIA-Based Analogues of Imidazole Alkaloid Act as Potent Inhibitors To Block Breast Cancer Invasion and Metastasis in Vivo
  作者：Qiong Wu、Kangdi Zheng、Xiaoting Huang、Li Li、Wenjie Mei

  DOI：10.1021/acs.jmedchem.8b01018

  日期：2018.12.13

  Tanshinone-IIA (Tan-IIA), a primary active component extracted from commonly used Chinese herbal, Salvia miltiorrhiza (Danshen), is considered as a potential inhibitor against tumor cell proliferation. However, the potential application of Tan-IIA is hindered by its poor water solubility and low bioavailability. In this work, an imidazole moiety was linked to the skeleton of Tan-IIA to enhance its antitumor activity. A series of Tan-IIA-based analogues TA01-TA12 were synthesized, and their inhibitory activities against the migration and invasion of MDA-MB-231 cells were investigated. All compounds, particularly TA12, markedly inhibited the proliferation, migration, and invasion of MDA-MB-231cells. TA12 also prominently blocked cancer cell metastasis in blood vessels and surrounding tissues in zebrafish xenograft model. Further studies showed that the mechanisms may involve S-phase arrest pathway, which was probably caused by inducing reactive oxygen species production and activating DNA damage. These results indicated that the Tan-IIA-based analogues of imidazole derivates can act as potent antimetastasis agents.
• Synthesis of novel tanshinone derivatives for treatment of castration‐resistant prostate cancer
  作者：Defeng Xu、Hang Hu、Jing Guan、Jun Da、Yipeng Xie、Yalin Liu、Ren Kong、Guoqiang Song、Huan Zhou

  DOI：10.1111/cbdd.13567

  日期：2019.9

  AbstractProstate cancer is the second leading cause of death in USA and has developed serious resistance to current drugs. Thus, development of new drugs for the treatment of castration‐resistant prostate cancer (CRPC) is urgently needed. In this study, 25 novel derivatives of tanshinone IIA as potential androgen receptor (AR) suppression reagents for the treatment of CRPC have been synthesized. The inhibition on DHT‐mediated AR transactivation and cell viability assay were performed to test the synthesized compounds. The results showed that among 25 new compounds, seven methoxy‐substituted tanshinone IIA derivatives showed significant inhibition effect on DHT‐mediated AR transactivation. In particular, TAN‐24 that contains three methoxy groups showed the strongest inhibition effect on DHT‐mediated AR transactivation. In addition, TAN‐24 also suppressed DHT‐AR transactivation more effectively than those of tanshinoneIIA and enzalutamide. In cytotoxicity against human prostate cancer cell lines assay, TAN‐24 exhibited the most potent in vitro cytotoxicity against LNCaP and CWR22Rv1 cells, with IC50 values 20‐ and 19‐times lower than those of tanshinone IIA and comparable to enzalutamide. TAN‐24 reported in the present work represents a novel and effective AR suppression drug, showing great potential for the treatment of CRPC.