8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione | 133130-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione
• 英文别名: 1,2,3,4-Tetrahydro-1,1-dimethyl-5,6-phenanthrenchinon；3,4-Phenanthrenedione, 5,6,7,8-tetrahydro-8,8-dimethyl-；8,8-dimethyl-6,7-dihydro-5H-phenanthrene-3,4-dione
• CAS: 133130-80-0
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: NUJIKIJQCXNJFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-甲氧基苯甲酰基)丙酸 在 钯 氢氧化钾 、 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 磷酸 、 三氟化硼乙醚 、 phosphorus pentoxide 、 三溴化硼 、 一水合肼 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 二乙二醇 为溶剂， 反应 30.0h， 生成 8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Tanshinone Analogues

  摘要：

  DOI：

  10.1023/b:conc.0000003428.26731.7f

文献信息

• Compounds from Danshen. Part 4. Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen)
  作者：Hson Mou Chang、Kuk Ying Chui、Fan Wah Lau Tan、Yun Yang、Zeng Pei Zhong、Chi Ming Lee、Hing Leung Sham、Henry N. C. Wong

  DOI：10.1021/jm00109a022

  日期：1991.5

  Twenty one o-quinonoid-type compounds and one coumarin-type compound related to miltirone (1) have been synthesized with the aim to identify the key structural elements involved in miltirone's interaction with the central benzodiazepine receptor. On the basis of their inhibition of [H-3]flunitrazepam binding to bovine cerebral cortex membranes, it is apparent that ring A of miltirone is essential for affinity. Although increasing the size of ring A from six-membered to seven- and eight-membered is well-tolerated, the introduction of polar hydroxyl groups greatly reduces binding affinity. The presence of 1,1-dimethyl groups on ring A is, however, not essential. On the other hand, the isopropyl group on ring C appears to be critical for binding as its removal decreases affinity by more than 30-fold. It can, however, be replaced with a methyl group with minimal reduction in affinity. Finally, linking ring A and B with a -CH2CH2- bridge results in analogue 89, which is 6 times more potent than miltirone at the central benzodiazepine receptor (IC50 = 0.05-mu-M).
• Synthesis and Antioxidant Activity of Rosmariquinone and Several Analogues
  作者：Clifford A. Hall、Susan L. Cuppett、Pat Dussault

  DOI：10.1021/jf970742k

  日期：1998.4.1

  Rosmariquinone (1) and six analogues were chemically synthesized using an ultrasound-promoted Diels-Alder cycloaddition in yields of 35-90%. The analogues included substitution of the isopropyl at carbon 13 (C-13) with a hydrogen (5), methyl (6), or tert-butyl (4) substituent. The hydrogen-substituted analogue had the lowest yield at 35%, due in part to the instability of the compound to air, while the highest yields were achieved for the methyl (85%) and tert-butyl (90%) analogues. The 60% yield obtained for the C-14 methyl analogue (7; no C-13 isopropyl) may have been caused by the meta-substituted catechol inhibiting the cycloaddition. The final two analogues were ring A modifications and included the removal of one C-4 methyl (3; 80% yield) or both C-4 methyl (2; 85% yield) groups. The analogues were tested against rosmariquinone in light-sensitized oxidation of stripped soybean oil. Analogues 5 and 6 were significantly (P < 0.05) better antioxidants than rosmariquinone and all other analogues. The antioxidant properties of compounds 2-7 were not significantly different (P < 0.05) from each other while compounds 2 and 4 had significantly (P < 0.05) lower antioxidant activity than rosmariquinone. This study demonstrated the importance of structural characteristics of antioxidants and that natural antioxidants, such as rosmariquinone, can be improved through chemical modification.
• CHANG, HSON MOU;CHUI, KUK YING;TAN, FAN WAH LAU;YANG, YUN;ZHONG, ZENG PEI+, J. MED. CHEM., 34,(1991) N, C. 1675-1692
  作者：CHANG, HSON MOU、CHUI, KUK YING、TAN, FAN WAH LAU、YANG, YUN、ZHONG, ZENG PEI+

  DOI：——

  日期：——