6-bromomethyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene | 193954-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6-bromomethyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene
• 英文别名: 6-(bromomethyl)-1,1,4,4,7-pentamethyl-2,3-dihydronaphthalene
• CAS: 193954-38-0
• 化学式: C₁₆H₂₃Br
• 分子量: 295.263
• InChiKey: PMFJLSUMFNXZBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  6-bromomethyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene 在 氢氧化钾 、 正丁基锂 、 四乙基溴化铵 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2E,4E)-3-Methyl-5-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopentyl]-penta-2,4-dienoic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of potent conformationally restricted retinoid X receptor ligands

  摘要：

  A series of potent retinoid X receptor (RXR) selective ligands were designed and prepared. The lead compound 6a, showed good binding (K-d; 3-7 nM) and transactivation (EC50; 19-24 nM) to the RXR subfamily of retinoid receptors. More importantly, a small variation on the aromatic ring moiety led to 6b, which had less residual RAR agonist activity with RXR binding and potency of 4-5 nM and 5-13 nM, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10079-8

文献信息

• Aromatic polycyclic retinoid-type derivatives, method for preparing same, and use thereof for making pharmaceutical and cosmetic compositions
  申请人：Centre Europeen de Bioprospective-Ceb

  公开号：US06265423B1

  公开（公告）日：2001-07-24

  Novel aromatic polycyclic retinoid-type derivatives of general formula (I), wherein groupings R3 and R4 attached to the double bond between carbons 11 and 12 are cis groupings, and pharmaceutical and cosmetic compositions containing same, are disclosed.

  本发明公开了一种通式（I）的新型芳香族多环视黄醇衍生物，其中连接在碳11和碳12之间的双键上的基团R3和R4为顺式基团，并且公开了含有该衍生物的药物和化妆品组合物。
• DERIVES POLYCYCLIQUES AROMATIQUES DE TYPE RETINOIDE, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION POUR LA FABRICATION DE COMPOSITIONS PHARMACEUTIQUES ET COSMETIQUES
  申请人：Centre Europeen de Bioprospective -CEB

  公开号：EP0879223B1

  公开（公告）日：2001-11-07
• US6265423B1
  申请人：——

  公开号：US6265423B1

  公开（公告）日：2001-07-24
• [EN] AROMATIC POLYCYCLIC RETINOID-TYPE DERIVATIVES, METHOD FOR PREPARING SAME, AND USE THEREOF FOR MAKING PHARMACEUTICAL AND COSMETIC COMPOSITIONS<br/>[FR] DERIVES POLYCYCLIQUES AROMATIQUES DE TYPE RETINOIDE, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION POUR LA FABRICATION DE COMPOSITIONS PHARMACEUTIQUES ET COSMETIQUES
  申请人：CENTRE EUROPEEN DE BIOPROSPECTIVE - CEB

  公开号：WO1997026237A1

  公开（公告）日：1997-07-24

  (EN) Novel aromatic polycyclic retinoid-type derivatives of general formula (I), wherein groupings R3 and R4 attached to the double bond between carbons 11 and 12 are cis groupings, and pharmaceutical and cosmetic compositions containing same, are disclosed.(FR) La présente invention concerne de nouveaux dérivés polycycliques aromatiques de type rétinoïde de la formule générale (I), dans laquelle les groupements R3 et R4 portés par la double liaison entre les carbones 11 et 12 sont en cis, ainsi que les compositions pharmaceutiques et cosmétiques les contenant.
• Synthesis and structure-activity relationships of potent conformationally restricted retinoid X receptor ligands
  作者：Luc J. Farmer、Lin Zhi、Susan Jeong、E. Adam Kallel、Glenn Croston、Karen S. Flatten、Rich A. Heyman、Alex M. Nadzan

  DOI：10.1016/s0960-894x(97)10079-8

  日期：1997.11

  A series of potent retinoid X receptor (RXR) selective ligands were designed and prepared. The lead compound 6a, showed good binding (K-d; 3-7 nM) and transactivation (EC50; 19-24 nM) to the RXR subfamily of retinoid receptors. More importantly, a small variation on the aromatic ring moiety led to 6b, which had less residual RAR agonist activity with RXR binding and potency of 4-5 nM and 5-13 nM, respectively. (C) 1997 Elsevier Science Ltd.