5-[(9H-purin-6-ylamino)methylene]-2-thioxodihydropyrimidine-4,6-dione | 1449744-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 5-[(9H-purin-6-ylamino)methylene]-2-thioxodihydropyrimidine-4,6-dione
• 英文别名: 5-[(7H-purin-6-ylamino)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione
• CAS: 1449744-92-6
• 化学式: C₁₀H₇N₇O₂S
• 分子量: 289.277
• InChiKey: AURMAWROKJZUHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124.69
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  腺嘌呤 以 水 为溶剂， 生成 5-[(9H-purin-6-ylamino)methylene]-2-thioxodihydropyrimidine-4,6-dione
  参考文献：
  名称：

  Design and synthesis of novel nucleobase-based barbiturate derivatives as potential anticancer agents

  摘要：

  Cancer today remains one of the most deadly diseases in the world. In search of novel anticancer agents, a series of newly hybrid molecules were designed and synthesized by combining the structural features of nucleobase and barbiturate derivatives using the concept of green chemistry. This approach was accomplished efficiently using the aqueous medium to give the corresponding products in a high yield. The newly synthesized compounds were characterized by spectral analysis FT-IR, H-1 NMR, C-13-NMR, HMBC, MASS and elemental analysis. Evaluations of these molecules over four cell lines panel of human cancer cells have identified several compounds with significant anticancer activities against one or more cell lines. Compounds TBC and TBA proved to exhibit a wide cytotoxic effect on the tested four cell lines at ( IC50 16-24 mu M) and ( IC50 25-34 mu M), respectively. Other compounds, e. g., 1,3-BA, showed a selective cytotoxicity against HepG2 at 7 mu M. Taken together, this study has led to the development of a convenient, a highly yielded, and an environmentally friendly synthetic method of highly promising leads for cancer fighting.

  DOI：

  10.1007/s00044-013-0683-4

文献信息

• Design and synthesis of novel nucleobase-based barbiturate derivatives as potential anticancer agents
  作者：Bhaveshkumar D. Dhorajiya、Ahmed S. Ibrahim、Farid A. Badria、Bharatkumar Z. Dholakiya

  DOI：10.1007/s00044-013-0683-4

  日期：2014.2

  Cancer today remains one of the most deadly diseases in the world. In search of novel anticancer agents, a series of newly hybrid molecules were designed and synthesized by combining the structural features of nucleobase and barbiturate derivatives using the concept of green chemistry. This approach was accomplished efficiently using the aqueous medium to give the corresponding products in a high yield. The newly synthesized compounds were characterized by spectral analysis FT-IR, H-1 NMR, C-13-NMR, HMBC, MASS and elemental analysis. Evaluations of these molecules over four cell lines panel of human cancer cells have identified several compounds with significant anticancer activities against one or more cell lines. Compounds TBC and TBA proved to exhibit a wide cytotoxic effect on the tested four cell lines at ( IC50 16-24 mu M) and ( IC50 25-34 mu M), respectively. Other compounds, e. g., 1,3-BA, showed a selective cytotoxicity against HepG2 at 7 mu M. Taken together, this study has led to the development of a convenient, a highly yielded, and an environmentally friendly synthetic method of highly promising leads for cancer fighting.