(4-amino-2-p-tolylaminothiazol-5-yl)-(3,4,5-trimethoxyphenyl)-methanone | 1186226-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-amino-2-p-tolylaminothiazol-5-yl)-(3,4,5-trimethoxyphenyl)-methanone
• 英文别名: [4-Amino-2-(4-methylanilino)-1,3-thiazol-5-yl]-(3,4,5-trimethoxyphenyl)methanone
• CAS: 1186226-92-5
• 化学式: C₂₀H₂₁N₃O₄S
• 分子量: 399.47
• InChiKey: NTEUDVRRVCLVJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氰胺 、 2-溴-1-(3,4,5-三甲氧基苯基)乙酮 、 对甲苯异硫氰酸酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以47%的产率得到(4-amino-2-p-tolylaminothiazol-5-yl)-(3,4,5-trimethoxyphenyl)-methanone
  参考文献：
  名称：

  2-Arylamino-4-Amino-5-Aroylthiazoles. “One-Pot” Synthesis and Biological Evaluation of a New Class of Inhibitors of Tubulin Polymerization

  摘要：

  The essential role of microtubules in mitosis makes them a major target of compounds useful for cancer therapy. In our search for potent antitumor agents, a novel series of 2-anilino-4-amino-5-aroylthiazoles was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. SAR was elucidated with various substitutions on the phenylamino and aroyl moiety at the 2- and 5-positions, respectively, of the 4-aminothiazole skeleton. Tumor cell exposure to several of these compounds led to the arrest of HeLa cells in the G2/M phase of the cell cycle and induction of apoptosis.

  DOI：

  10.1021/jm9001692

文献信息

• 2-Arylamino-4-Amino-5-Aroylthiazoles. “One-Pot” Synthesis and Biological Evaluation of a New Class of Inhibitors of Tubulin Polymerization
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Olga Cruz-Lopez、Carlota Lopez Cara、Giuseppe Basso、Giampietro Viola、Mohammed Khedr、Jan Balzarini、Siavosh Mahboobi、Andreas Sellmer、Andrea Brancale、Ernest Hamel

  DOI：10.1021/jm9001692

  日期：2009.9.10

  The essential role of microtubules in mitosis makes them a major target of compounds useful for cancer therapy. In our search for potent antitumor agents, a novel series of 2-anilino-4-amino-5-aroylthiazoles was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. SAR was elucidated with various substitutions on the phenylamino and aroyl moiety at the 2- and 5-positions, respectively, of the 4-aminothiazole skeleton. Tumor cell exposure to several of these compounds led to the arrest of HeLa cells in the G2/M phase of the cell cycle and induction of apoptosis.