2--oestron-3-methylether | 21003-04-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 2--oestron-3-methylether
• 英文别名: (8R,9S,13S,14S)-7,8,9,11,12,13,15,16-octahydro-2-adamantyl-3-methoxy-13-methyl-6H-cyclopenta[a]phenanthrene-17(14H)-one；2-(Adamantyl-(1))-oestron-3-methylether
• CAS: 21003-04-3
• 化学式: C₂₉H₃₈O₂
• 分子量: 418.62
• InChiKey: QGTVEUIHCNUHKL-DGGJTPRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2--oestron-3-methylether 在 甲醇 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 (8R,9S,13S,14S)-methyl 7,8,9,11,12,13,14,15,16,17-decahydro-17-hydroxy-2-adamantyl-3-methoxy-13-methyl-6H-cyclopenta[a]phenanthrene-16-carboxylate
  参考文献：
  名称：

  Targeting RORs nuclear receptors by novel synthetic steroidal inverse agonists for autoimmune disorders

  摘要：

  Designing novel inverse agonists of NR ROR gamma t still represents a challenge for the pharmaceutical community to develop therapeutics for treating immune diseases. By exploring the structure of NRs natural ligands, the representative arotenoid ligands and RORs specific ligands share some chemical homologies which can be exploited to design a novel molecular structure characterized by a polycyclic core bearing a polar head and a hydrophobic tail. Compound MG 2778 (8), a cyclopenta[a]phenantrene derivative, was identified as lead compound which was chemically modified at position 2 in order to obtain a small library for preliminary SARs. Cell viability and estrogenic activity of compounds 7, 8, 19a, 30, 31 and 32 were evaluated to attest selectivity. The selected 7, 8, 19a and 31 compounds were assayed in a Gal4 UAS-Luc co-transfection system in order to determine their ability to modulate ROR gamma t activity in a cellular environment. They were evaluated as inverse agonists taken ursolic acid as reference compound. The potency of compounds was lower than that of ursolic acid, but their efficacy was similar. Compound 19a was the most active, significantly reducing ROR gamma t activity at low micromolar concentrations. (c) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.02.018
• 作为产物：
  描述：

  雌酚酮 在 三氟化硼乙醚 、 四丁基碘化铵 、 sodium hydroxide 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2--oestron-3-methylether
  参考文献：
  名称：

  Targeting RORs nuclear receptors by novel synthetic steroidal inverse agonists for autoimmune disorders

  摘要：

  Designing novel inverse agonists of NR ROR gamma t still represents a challenge for the pharmaceutical community to develop therapeutics for treating immune diseases. By exploring the structure of NRs natural ligands, the representative arotenoid ligands and RORs specific ligands share some chemical homologies which can be exploited to design a novel molecular structure characterized by a polycyclic core bearing a polar head and a hydrophobic tail. Compound MG 2778 (8), a cyclopenta[a]phenantrene derivative, was identified as lead compound which was chemically modified at position 2 in order to obtain a small library for preliminary SARs. Cell viability and estrogenic activity of compounds 7, 8, 19a, 30, 31 and 32 were evaluated to attest selectivity. The selected 7, 8, 19a and 31 compounds were assayed in a Gal4 UAS-Luc co-transfection system in order to determine their ability to modulate ROR gamma t activity in a cellular environment. They were evaluated as inverse agonists taken ursolic acid as reference compound. The potency of compounds was lower than that of ursolic acid, but their efficacy was similar. Compound 19a was the most active, significantly reducing ROR gamma t activity at low micromolar concentrations. (c) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.02.018

文献信息

• The adamantyl carbonium ion as a dehydrogenating agent, its reactions with estrone
  作者：W.H.W. Lunn、E. Farkas

  DOI：10.1016/s0040-4020(01)96851-6

  日期：1968.1

  An unusual and useful dehydrogenation of estrone of Δ9(11)-estrone has been observed on its reaction with the adamantyl carbonium ion. With modified conditions both t-butyl and adamantyl carbonium ion sources gave 2-substituted estrone derivatives in this reaction.

  在与金刚烷基碳酸根离子反应时，已观察到Δ9 （11） -雌酮的雌酮异常且有用的脱氢。在改变的条件下，叔丁基和金刚烷基碳离子源均在该反应中得到2-取代的雌酮衍生物。