(1S,2S)-7-Isopropyl-1-methyl-1,2,3,4-tetrahydro-phenanthrene-1,2,6-triol | 133130-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2S)-7-Isopropyl-1-methyl-1,2,3,4-tetrahydro-phenanthrene-1,2,6-triol
• 英文别名: (1S,2R)-7-Isopropyl-1-methyl-1,2,3,4-tetrahydro-phenanthrene-1,2,6-triol
• CAS: 133130-65-1
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: LEFZXSGFOUHKDI-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-7-Isopropyl-1-methyl-1,2,3,4-tetrahydro-phenanthrene-1,2,6-triol 在 sodium hydroxide 、 potassium dihydrogenphosphate 、 potassium nitrososulfonate 作用下， 以 丙酮 为溶剂， 反应 36.0h， 生成 1-methyl-cis-1,2-dihydroxy-1,2,3,4-tetrahydro-7-isopropylphenanthrene-5,6-dione
  参考文献：
  名称：

  Compounds from Danshen. Part 4. Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen)

  摘要：

  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).

  DOI：

  10.1021/jm00109a022
• 作为产物：
  描述：

  3,4-dihydro-6-(benzyloxy)-7-isopropylphenanthren-1(2H)-one 在 palladium on activated charcoal 四氧化锇 、 氢气 、 甲基磺酰氯 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 (1S,2S)-7-Isopropyl-1-methyl-1,2,3,4-tetrahydro-phenanthrene-1,2,6-triol
  参考文献：
  名称：

  Compounds from Danshen. Part 4. Structure-activity relationship of miltirone, an active central benzodiazepine receptor ligand isolated from Salvia miltiorrhiza Bunge (Danshen)

  摘要：

  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).

  DOI：

  10.1021/jm00109a022