1-(5,5,8,8-Tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopentane-1-carbaldehyde | 199988-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-(5,5,8,8-Tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopentane-1-carbaldehyde
• 英文别名: 1-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopentane-1-carbaldehyde
• CAS: 199988-71-1
• 化学式: C₂₀H₂₈O
• 分子量: 284.442
• InChiKey: NEDWSXUWZVLJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(5,5,8,8-Tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopentane-1-carbaldehyde 在 N,N-二甲基丙烯基脲 、 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 生成 (2E,4E)-3-Methyl-6-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopentyl]-hexa-2,4-dienoic acid
  参考文献：
  名称：

  Retinoic acid receptor ligands based on the 6-cyclopropyl-2,4-hexadienoic acid

  摘要：

  A series of novel cyclopropanyl methyl hexadienoic acid retinoids was designed and prepared. These compounds exhibited either selective activity as RXR agonists or pan-agonists on one or more of each of the RAR and RXR isoforms. The most potent pan-agonist 5a (RAR's EC50 = 17-59 nM; RXR's EC50 6-14 nM) showed good antiproliferative properties in the in vitro cancer cell lines, ME 180 and RPMI 8226. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00924-1
• 作为产物：
  描述：

  6-(溴甲基)-1,2,3,4-四氢-1,1,4,4,-四甲基萘 在 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 1-(5,5,8,8-Tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopentane-1-carbaldehyde
  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