6-methoxy-N-(2-methoxyphenyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-methoxy-N-(2-methoxyphenyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-amine
• 化学式: C₁₈H₁₇N₃O₂
• 分子量: 307.352
• InChiKey: WYGFYFKVMSHREG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基-1-茚酮 、 异氰酸2-甲氧苯酯 在 lithium hexamethyldisilazane 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以40%的产率得到6-methoxy-N-(2-methoxyphenyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-amine
  参考文献：
  名称：

  Methyl 3-((6-Methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)amino)benzoate (GN39482) as a Tubulin Polymerization Inhibitor Identified by MorphoBase and ChemProteoBase Profiling Methods

  摘要：

  A series of indenopyrazoles was synthesized from the corresponding indanones arid phenyl isothiocyanates in two steps. Among the compounds synthesized, methyl 3-((6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)amino)benzoate 6m (GN39482) was found to possess a promising antiproliferative activity toward human cancer cells without affecting any antimicrobial and antimalarial activities at 100 nM. Both a methoxy group at R-1 position and a methoxycarbonyl group at R-2 position of the anilinoquinazoline framework are essential for the high cell growth inhibition. Both MorphoBase and ChemProteoBase profiling analyses suggested that compound 6m was classified as a tubulin inhibitor. Indeed, compound 6m inhibited the acetylated tubulin accumulation and the microtubule formation and induced G2/M cell. Cycle arrest in HeLa cells, revealing that a promising aritiproliferative activity of compound 6m toward human cancer cells is probably caused by the tubulin polymerization inhibition.

  DOI：

  10.1021/acs.jmedchem.5b00035