4-N-ethylidenecytosine acetate | 1400898-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-N-ethylidenecytosine acetate
• CAS: 1400898-66-9
• 化学式: C₂H₄O₂*C₆H₇N₃O
• 分子量: 197.194
• InChiKey: JQIVCFBSUSNRBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95.41
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-N-ethylidenecytosine acetate 在 dimethyl sulfide borane 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 24.0h， 以57%的产率得到6-(乙基氨基)-2(1H)-嘧啶酮
  参考文献：
  名称：

  New cytosine derivatives as inhibitors of DNA methylation

  摘要：

  DNA cytosine methylation catalyzed by DNA methyltransferase 1 (DNMT1) is an epigenetic method of gene expression regulation and development. Changes in methylation pattern lead to carcinogenesis. Inhibition of DNMT1 activity could be a good strategy of safe and efficient epigenetic therapy. In this work, we present a novel group of cytosine analogs as inhibitors of DNA methylation. We show new methods of synthesis and their effect on in vitro reaction of DNA methylation. Almost all of analyzed compounds inhibit DNA methyltransferase activity in the competitive manner. K-i values for the most potent compound 4-N-furfuryl-5,6-dihydroazacytosines is 0.7 mu M. These compounds cause also a decrease of 5-methylcytosine (m(5)C) level in DNA of mammalian HeLa and HEK293 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.024
• 作为产物：
  描述：

  胞嘧啶 、 乙醛 、 溶剂黄146 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到4-N-ethylidenecytosine acetate
  参考文献：
  名称：

  New cytosine derivatives as inhibitors of DNA methylation

  摘要：

  DNA cytosine methylation catalyzed by DNA methyltransferase 1 (DNMT1) is an epigenetic method of gene expression regulation and development. Changes in methylation pattern lead to carcinogenesis. Inhibition of DNMT1 activity could be a good strategy of safe and efficient epigenetic therapy. In this work, we present a novel group of cytosine analogs as inhibitors of DNA methylation. We show new methods of synthesis and their effect on in vitro reaction of DNA methylation. Almost all of analyzed compounds inhibit DNA methyltransferase activity in the competitive manner. K-i values for the most potent compound 4-N-furfuryl-5,6-dihydroazacytosines is 0.7 mu M. These compounds cause also a decrease of 5-methylcytosine (m(5)C) level in DNA of mammalian HeLa and HEK293 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.024