[4-amino-2-(3-methoxyphenylamino)-thiazol-5-yl]-phenylmethanone | 1111055-66-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4-amino-2-(3-methoxyphenylamino)-thiazol-5-yl]-phenylmethanone
• 英文别名: [4-Amino-2-(3-methoxyanilino)-1,3-thiazol-5-yl]-phenylmethanone
• CAS: 1111055-66-3
• 化学式: C₁₇H₁₅N₃O₂S
• 分子量: 325.391
• InChiKey: BMACDARQSMTWPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氰胺 、 2-溴苯乙酮 、 3-甲氧基异硫氰酸苯酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以58%的产率得到[4-amino-2-(3-methoxyphenylamino)-thiazol-5-yl]-phenylmethanone
  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.