6-{Ethyl-[4-isopropyl-3-(3-phenylpropoxy)phenyl]amino}nicotinic acid | 1240481-50-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-{Ethyl-[4-isopropyl-3-(3-phenylpropoxy)phenyl]amino}nicotinic acid
• 英文别名: 6-[N-ethyl-3-(3-phenylpropoxy)-4-propan-2-ylanilino]pyridine-3-carboxylic acid
• CAS: 1240481-50-8
• 化学式: C₂₆H₃₀N₂O₃
• 分子量: 418.536
• InChiKey: NSJIEKPNKVMLGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 6-(ethyl(3-isopropoxy-4-isopropylphenyl)amino)nicotinate 在 aluminum (III) chloride 、 水 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-{Ethyl-[4-isopropyl-3-(3-phenylpropoxy)phenyl]amino}nicotinic acid
  参考文献：
  名称：

  Modification at the Lipophilic Domain of RXR Agonists Differentially Influences Activation of RXR Heterodimers

  摘要：

  RXR permissive heterodimers are reported to be activated differently depending upon the chemical structure of RXR agonists, but the relationship of agonist structure to differential heterodimer activation has not been explored in detail. In this study, we performed systematic conversion of the alkoxy side chain of 5a (6-[ethyl-(3-isopropoxy-4-isopropylphenyl)amino]nicotinic acid, NEt-3IP) and evaluated the RXR-, PPAR/RXR-, and LXR/RXR-agonist activities of the products. The cyclopropylmethoxy analogue (5c) showed similar RXR- and LXR/RXR-agonistic activities to the benzyloxy analogue (51) and n-propoxy analogue (5k) but exhibited more potent PPAR/RXR-agonistic activity than 51 or 5k. Differential modulation of RXR heterodimer-activating ability by conversion of the alkoxy group located in the lipophilic domain of the RXR-agonist common structure is expected be a useful approach in the design of new RXR agonists for the treatment of hyperlipidemia or type 2 diabetes.

  DOI：

  10.1021/ml100184k

文献信息

• Modification at the Lipophilic Domain of RXR Agonists Differentially Influences Activation of RXR Heterodimers
  作者：Fuminori Ohsawa、Ken-ichi Morishita、Shoya Yamada、Makoto Makishima、Hiroki Kakuta

  DOI：10.1021/ml100184k

  日期：2010.12.9

  RXR permissive heterodimers are reported to be activated differently depending upon the chemical structure of RXR agonists, but the relationship of agonist structure to differential heterodimer activation has not been explored in detail. In this study, we performed systematic conversion of the alkoxy side chain of 5a (6-[ethyl-(3-isopropoxy-4-isopropylphenyl)amino]nicotinic acid, NEt-3IP) and evaluated the RXR-, PPAR/RXR-, and LXR/RXR-agonist activities of the products. The cyclopropylmethoxy analogue (5c) showed similar RXR- and LXR/RXR-agonistic activities to the benzyloxy analogue (51) and n-propoxy analogue (5k) but exhibited more potent PPAR/RXR-agonistic activity than 51 or 5k. Differential modulation of RXR heterodimer-activating ability by conversion of the alkoxy group located in the lipophilic domain of the RXR-agonist common structure is expected be a useful approach in the design of new RXR agonists for the treatment of hyperlipidemia or type 2 diabetes.