(4-chlorophenyl)[5-(4-chlorophenyl)thieno[2,3-d]pyrimidin-4-yl]amine | 329708-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: (4-chlorophenyl)[5-(4-chlorophenyl)thieno[2,3-d]pyrimidin-4-yl]amine
• 英文别名: N,5-bis(4-chlorophenyl)thieno[2,3-d]pyrimidin-4-amine
• CAS: 329708-97-6
• 化学式: C₁₈H₁₁Cl₂N₃S
• mdl: MFCD02677415
• 分子量: 372.277
• InChiKey: PJHCDRSJAMWULG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-4-(4-氯苯基)-3-甲酸乙酯基噻吩 在 三氯氧磷 作用下， 以 异丙醇 为溶剂， 反应 0.75h， 生成 (4-chlorophenyl)[5-(4-chlorophenyl)thieno[2,3-d]pyrimidin-4-yl]amine
  参考文献：
  名称：

  Novel Dual Use of Formamide-POCl₃ Mixture for the Efficient, One-Pot Synthesis of Condensed 2H-Pyrimidin-4-amine Libraries Under Microwave Irradiation

  摘要：

  The novel dual use of formamide-POCl3 mixture for the incorporation of a C-N fragment to form the pyrimidine nucleus and its subsequent chlorination in an efficient, one-pot synthesis of potentially bioactive condensed 2H-pyrimidin-4-amine libraries under microwave irradiation (MWI) is reported. The one-pot microwave-assisted synthetic protocol is high-yielding, ecofriendly, rapid, and novel as well as eliminates intermittent work-ups. The protocol can be adapted for the library synthesis of series of a condensed pyrimidines.

  DOI：

  10.1080/00397911.2011.607934

文献信息

• Design, Synthesis and Biological Evaluation of Some 5-Arylthieno[2,3-<i>d</i>]pyrimidines as Potential Anti-cancer Agents
  作者：Afaf Kamal El-Ansary、Aliaa Mohammed Kamal、Mokhtar Abd-Hafiz Al-Ghorafi

  DOI：10.1248/cpb.c16-00291

  日期：——

  Structure-based design, synthesis and biological evaluation of new small molecules anti-cancer agents were described. On continuation of applying scaffold hopping theory, a series of 5-arylthieno[2,3-d]pyrimidines based on the structural features of lapatinib was designed, synthesized and characterized using IR, 1H-NMR, 13C-NMR, mass and microanalyses. Biological evaluation of the cytotoxic activity against MCF-7 cell line and the inhibition of the enzymatic activity of epidermal growth factor tyrosine kinase were carried out in vitro for the target compounds. Substituting the 4-anilino-5-arylthieno[2,3-d]pyrimidines with different pharmacophoric groups at ortho, meta and/or para positions led to discovery of two potent lead compounds 3b and f with excellent cytotoxic activity and enzymatic inhibition activity.

  基于结构的药物设计、合成和生物评价的新型小分子抗癌剂被详细描述。在延续应用骨架跃迁理论的基础上，根据拉帕替尼的结构特征，设计、合成了基于5-芳基噻吩并[2,3-d]嘧啶的一系列化合物，并通过IR、1H-NMR、13C-NMR、质谱和微量分析进行了表征。针对目标化合物，进行体外细胞毒活性对MCF-7细胞系的生物评价和表皮生长因子酪氨酸激酶的酶活性抑制试验。将4-苯胺基-5-芳基噻吩并[2,3-d]嘧啶中的不同药效团在邻位、间位和/或对位进行取代，发现了两种具有优异细胞毒活性和酶抑制活性的强效先导化合物3b和f。
• Novel Dual Use of Formamide-POCl₃ Mixture for the Efficient, One-Pot Synthesis of Condensed 2<i>H</i>-Pyrimidin-4-amine Libraries Under Microwave Irradiation
  作者：Kishore S. Jain、Muthu K. Kathiravan、Jitender B. Bariwal、Pratip K. Chaskar、Santosh S. Tompe、Nikhilesh Arya

  DOI：10.1080/00397911.2011.607934

  日期：2013.1.1

  The novel dual use of formamide-POCl3 mixture for the incorporation of a C-N fragment to form the pyrimidine nucleus and its subsequent chlorination in an efficient, one-pot synthesis of potentially bioactive condensed 2H-pyrimidin-4-amine libraries under microwave irradiation (MWI) is reported. The one-pot microwave-assisted synthetic protocol is high-yielding, ecofriendly, rapid, and novel as well as eliminates intermittent work-ups. The protocol can be adapted for the library synthesis of series of a condensed pyrimidines.