4-chloro-5-(4-nitrophenyl)thieno[2,3-d]pyrimidine

• 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-chloro-5-(4-nitrophenyl)thieno[2,3-d]pyrimidine
• 化学式: C₁₂H₆ClN₃O₂S
• 分子量: 291.718
• InChiKey: YBVURUQXJIKEMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-5-(4-nitrophenyl)thieno[2,3-d]pyrimidine 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 (Z/E)N-(3,4-dimethoxybenzylidene)-N'-[5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-yl]hydrazine
  参考文献：
  名称：

  Synthesis and evaluation of 4-anilinoquinazoline bioisosteres as potential anti-breast cancer agents

  摘要：

  Based on one of the four major categories of scaffold hopping theory namely hetrocycle replacements, a series of 5-arylthieno[2,3-d]pyrimidines had been prepared and evaluated as anti-breast cancer agents. Optimization by combination of different pharmacophores with the thienopyrimidine scaffold led to discovery of biologically active compounds. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.056
• 作为产物：
  描述：

  2-氨基-4-(4-硝基苯基)-3-噻吩甲腈 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 36.0h， 生成 4-chloro-5-(4-nitrophenyl)thieno[2,3-d]pyrimidine
  参考文献：
  名称：

  Synthesis and evaluation of 4-anilinoquinazoline bioisosteres as potential anti-breast cancer agents

  摘要：

  Based on one of the four major categories of scaffold hopping theory namely hetrocycle replacements, a series of 5-arylthieno[2,3-d]pyrimidines had been prepared and evaluated as anti-breast cancer agents. Optimization by combination of different pharmacophores with the thienopyrimidine scaffold led to discovery of biologically active compounds. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.056

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。
• Synthesis and evaluation of 4-anilinoquinazoline bioisosteres as potential anti-breast cancer agents
  作者：Afaf K. El-Ansary、Aliaa M. Kamal、Mokhtar AbdHafiz Al-Ghorafi

  DOI：10.1016/j.ejmech.2014.08.056

  日期：2014.10

  Based on one of the four major categories of scaffold hopping theory namely hetrocycle replacements, a series of 5-arylthieno[2,3-d]pyrimidines had been prepared and evaluated as anti-breast cancer agents. Optimization by combination of different pharmacophores with the thienopyrimidine scaffold led to discovery of biologically active compounds. (c) 2014 Elsevier Masson SAS. All rights reserved.