ethyl 4-[N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)-N-(4-trifluoromethylbenzyl)amino]benzoate | 1300118-19-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 4-[N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)-N-(4-trifluoromethylbenzyl)amino]benzoate
• CAS: 1300118-19-7
• 化学式: C₃₁H₃₄F₃NO₂
• 分子量: 509.612
• InChiKey: GZTAVXLQQYEMDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.57
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-[N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)-N-(4-trifluoromethylbenzyl)amino]benzoate 在 potassium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以90%的产率得到4-[N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)-N-(4-trifluoromethylbenzyl)amino]benzoic acid
  参考文献：
  名称：

  Diphenylamine-based retinoid antagonists: Regulation of RAR and RXR function depending on the N-substituent

  摘要：

  Based upon the structure-activity relationships of diphenylamine derivatives with retinoid synergistic activity (RXR agonists), novel diphenylamine derivatives with a long alkyl chain (9a and 9b) or a benzyl group (10a-f) as the N-substituent were designed and synthesized. All the synthesized compounds dose-dependently inhibited HL-60 cell differentiation induced by 3.3 x 10 (10) M Am80. Among them, compound 10f showed the most potent inhibitory activity, and the mechanism was shown, by means of transactivation assay for RARs and RXRs, to involve antagonism against RARs. The N-substituent of the diphenylamine skeleton plays an important role in determining the receptor selectivity for RARs or RXRs, as well as the agonist or antagonist nature of the activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.026
• 作为产物：
  描述：

  5,6,7,8-四氢-5,5,8,8-四甲基-2-萘胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.33h， 生成 ethyl 4-[N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)-N-(4-trifluoromethylbenzyl)amino]benzoate
  参考文献：
  名称：

  Diphenylamine-based retinoid antagonists: Regulation of RAR and RXR function depending on the N-substituent

  摘要：

  Based upon the structure-activity relationships of diphenylamine derivatives with retinoid synergistic activity (RXR agonists), novel diphenylamine derivatives with a long alkyl chain (9a and 9b) or a benzyl group (10a-f) as the N-substituent were designed and synthesized. All the synthesized compounds dose-dependently inhibited HL-60 cell differentiation induced by 3.3 x 10 (10) M Am80. Among them, compound 10f showed the most potent inhibitory activity, and the mechanism was shown, by means of transactivation assay for RARs and RXRs, to involve antagonism against RARs. The N-substituent of the diphenylamine skeleton plays an important role in determining the receptor selectivity for RARs or RXRs, as well as the agonist or antagonist nature of the activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.026