(4-amino-2-p-tolylamino-thiazol-5-yl)-phenyl-methanone | 107401-68-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-amino-2-p-tolylamino-thiazol-5-yl)-phenyl-methanone
• 英文别名: (4-amino-2-p-tolylaminothiazol-5-yl)phenylmethanone；4-amino-5-benzoyl-2-(p-methylphenylamino)thiazole；[4-Amino-2-(4-methylanilino)-1,3-thiazol-5-yl]-phenylmethanone
• CAS: 107401-68-3
• 化学式: C₁₇H₁₅N₃OS
• 分子量: 309.392
• InChiKey: WNHKZUMEGWQAFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 (4-amino-2-p-tolylamino-thiazol-5-yl)-phenyl-methanone
  参考文献：
  名称：

  Studies on the Synthesis of 5-Acyl-2,4-diaminothiazoles from Amidinothioureas

  摘要：

  1-烷基或芳基-3-脒基硫脲与δ-卤酮反应或不反应，生成 5-酰基-2,4-二氨基噻唑。

  DOI：

  10.1055/s-1986-31634

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。
• An efficient protocol for solid phase aminothiazole synthesis
  作者：Kumaran G. Sreejalekshmi、Satyabhama K.C. Devi、Kallikat N. Rajasekharan

  DOI：10.1016/j.tetlet.2006.06.169

  日期：2006.8

  An efficient synthesis of 2,4-diamino-5-ketothiazoles under solid phase conditions has been achieved by the reaction of polymer supported amidinothioureas with α-haloketones. This novel synthetic approach involving traceless cleavage from the support is suited for automation, and allows solid phase combinatorial synthesis of 2,4-diamino-5-ketothiazoles in good yields and purities.

  在固相条件下，通过聚合物负载的mid基硫脲与α-卤代酮的反应已实现了2,4-二氨基-5-酮噻唑的有效合成。这种涉及从载体上无痕裂解的新颖合成方法适用于自动化，并允许以良好的收率和纯度进行固相组合合成2,4-二氨基-5-酮噻唑。
• 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.
• One-pot sequential multicomponent route to 2,4-diaminothiazoles—a facile approach to bioactive agents for cancer therapeutics
  作者：Kumaran G. Sreejalekshmi、Kallikat N. Rajasekharan

  DOI：10.1016/j.tetlet.2012.05.010

  日期：2012.7

  A facile one-pot sequential three-component route to 2,4-diaminothiazoles is reported. The new approach employs the mildest reaction conditions and commercially available reagents to generate diverse 2-alkyl/arylamino-4-amino-5-aroyl/heteroylthiazoles in short reaction times, good yield, and purity. (C) 2012 Elsevier Ltd. All rights reserved.
• SYNTHESIS AND CYCLIZATION OF 1-(<i>N</i>-NITROAMIDINO)THIOUREAS TO 2,4-DIAMINOTHIAZOLES
  作者：R. Binu、K. K. Thomas、G. C. Jenardanan、K. N. Rajasekharan

  DOI：10.1080/00304949809355265

  日期：1998.2