2-(4-methoxy-N-methylanilino)-6-(trifluoromethyl)pyridine-3-carboxylic acid | 1421676-46-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(4-methoxy-N-methylanilino)-6-(trifluoromethyl)pyridine-3-carboxylic acid
• CAS: 1421676-46-1
• 化学式: C₁₅H₁₃F₃N₂O₃
• 分子量: 326.275
• InChiKey: HRFYLQOULCMLJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(4-methoxy-N-methylanilino)-6-(trifluoromethyl)pyridine-3-carboxylic acid 、 碘乙烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以88%的产率得到ethyl 2-(4-methoxy-N-methylanilino)-6-(trifluoromethyl)pyridine-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of N-alkyl-N-(4-methoxyphenyl)pyridin-2-amines as a new class of tubulin polymerization inhibitors

  摘要：

  Based on our prior antitumor hits, 32 novel N-alkyl-N-substituted phenylpyridin-2-amine derivatives were designed, synthesized and evaluated for cytotoxic activity against A549, KB, KBVIN, and DU145 human tumor cell lines (HTCL). Subsequently, three new leads (6a, 7g, and 8c) with submicromolar GI(50) values of 0.19-0.41 mu M in the cellular assays were discovered, and these compounds also significantly inhibited tubulin assembly (IC50 1.4-1.7 mu M) and competitively inhibited colchicine binding to tubulin with effects similar to those of the clinical candidate CA-4 in the same assays. These promising results indicate that these tertiary diarylamine derivatives represent a novel class of tubulin polymerization inhibitors targeting the colchicine binding site and showing significant anti-proliferative activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.047
• 作为产物：
  描述：

  methyl 2-(4-methoxy-N-methylanilino)-6-(trifluoromethyl)pyridine-3-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 36.0h， 以72%的产率得到2-(4-methoxy-N-methylanilino)-6-(trifluoromethyl)pyridine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of N-alkyl-N-(4-methoxyphenyl)pyridin-2-amines as a new class of tubulin polymerization inhibitors

  摘要：

  Based on our prior antitumor hits, 32 novel N-alkyl-N-substituted phenylpyridin-2-amine derivatives were designed, synthesized and evaluated for cytotoxic activity against A549, KB, KBVIN, and DU145 human tumor cell lines (HTCL). Subsequently, three new leads (6a, 7g, and 8c) with submicromolar GI(50) values of 0.19-0.41 mu M in the cellular assays were discovered, and these compounds also significantly inhibited tubulin assembly (IC50 1.4-1.7 mu M) and competitively inhibited colchicine binding to tubulin with effects similar to those of the clinical candidate CA-4 in the same assays. These promising results indicate that these tertiary diarylamine derivatives represent a novel class of tubulin polymerization inhibitors targeting the colchicine binding site and showing significant anti-proliferative activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.047