[4-amino-2-(4-methoxyphenylamino)thiazol-5-yl](4-bromophenyl)methanone | 1111005-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4-amino-2-(4-methoxyphenylamino)thiazol-5-yl](4-bromophenyl)methanone
• 英文别名: 5-(4-Bromobenzoyl)-N2-(4-methoxyphenyl)-1,3-thiazole-2,4-diamine；[4-amino-2-(4-methoxyanilino)-1,3-thiazol-5-yl]-(4-bromophenyl)methanone
• CAS: 1111005-41-4
• 化学式: C₁₇H₁₄BrN₃O₂S
• mdl: MFCD14940691
• 分子量: 404.287
• InChiKey: KUZFXGGVFBBRGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 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 、 4-甲氧基苯基 异硫氰酸酯 、 2,4'-二溴苯乙酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以53%的产率得到[4-amino-2-(4-methoxyphenylamino)thiazol-5-yl](4-bromophenyl)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

• [EN] DIAMINOTHIAZOLE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS DE DIAMINOTHIAZOLE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：APOGEE BIOTECHNOLOGY CORP

  公开号：WO2018089902A1

  公开（公告）日：2018-05-17

  The disclosure relates to diaminothiazole derivatives of formula (I) where the variables are as defined herein, pharmaceutical compositions containing such compounds, and methods for the use of such compounds and compositions for the treatment of hyperproliferative, inflammatory or neurologic diseases and disorders.

  本公开涉及式(I)的二氨基噻唑衍生物，其中变量如本文所定义，以及含有这种化合物的药物组合物，以及使用这种化合物和组合物治疗过度增生性、炎症性或神经系统疾病和紊乱的方法。
• 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.